Worst Sports Contracts of All Time

Your reckless spending is nothing compared to these deals.

Every pro sports team or organization employs someone who specializes in contracts. Their job is to come up with appropriate contract offers for players while utilizing past performance, future potential and the market as guides. They scour through spreadsheets, talk with personnel departments and spend an inordinate amount of time to make sure that the contract’s value aligns with the athlete’s value. But mistakes are still made, and teams often overestimate what an athlete is worth.

That’s something that just comes with the territory of working in a sports front office. A player doesn’t live up to his contract, and those who negotiated the deal feel the heat. Bad contracts could be due to a variety of reasons such as poor performance, head-scratching clauses or special provisions. While most bad contracts produced a poor ROI for the teams that handed them out, others were bad for the athlete.

These are the worst of the worst sports contracts of all time.

100. Alex Rodriguez

A-Rod or A-Fraud? Charles Krupa / AP Photo

Sport: Baseball (MLB)

Year: 2008

Contract: 10 years, $275 million

Team: New York Yankees

Return on investment: 880 G, .269 AVG, 178 HR, 583 RBI

Bottom line: For the longest time, Alex Rodriguez owned the two largest contracts in sports history. First, he signed a 10-year, $252 million deal with the Texas Rangers in 2001, opted out after seven seasons and then signed the deal with the Yankees.

During this contract, Rodriguez was suspended an entire season for PEDs but instead of having his $25 million salary wiped from the books, the Yankees still had to pay him $3 million based on a provision in the contract.

Even though Rodriguez missed out on that $22 million, he still made over $450 million during his MLB career, which was more than any North American team sport athlete ever at the time of his retirement.

99. Sean Avery

Sean Avery did not deliver much production on the ice with the Dallas Stars. Tony Gutierrez / AP Photo

Sport: Hockey (NHL)

Year: 2008

Contract: 4 years, $15.5 million

Team: Dallas Stars

Return on investment: 23 GP, 3 G, 7 A, 10 PTS

Bottom line: This isn’t an example of nepotism, but it’s pretty damn close. Sean Avery was brought in because he was buddies with the team’s general manager who said that the Stars lacked a fiery personality.

Well, they apparently got too much fire as just five months into his tenure, Avery conducted an interview where he referred to his ex-girlfriends as “sloppy seconds” because they were dating other NHL players.

After being suspended, Avery’s teammates didn’t even want him to return so the team promptly waived him.

98. Jon Koncak

Jon Koncak, center, became known as “Jon Contract” for getting overpaid. Joe Holoway Jr. / AP Photo

Sport: Basketball (NBA)

Year: 1989

Contract: 6 years, $13.7 million

Team: Atlanta Hawks

Return on investment: 430 G, 3.6 PPG, 4.3 RPG, 1.0 BPG

Bottom line: Jon Koncak’s deal was so bad that afterward people nicknamed him “Jon Contract.”

His deal came at a time when only the top NBA players’ salaries were known so when people heard that a backup big man was being paid that much, they took notice. One of those people was Shaquille O’Neal who saw Koncak play while still in school and realized he could make a whole lot of money in the NBA if Koncak made nearly $14 million.

So, in a way, we can thank Koncak’s contract for helping motivate Shaq.

97. Dez Bryant

Dez Bryant never lived up to his potential. David J. Phillip / AP Photo

Sport: Football (NFL)

Year: 2010

Contract: 5 years, $12 million ($8.4 million guaranteed)

Team: Dallas Cowboys

Return on investment: 75 G, 381 REC, 5,424 YDS, 14.2 AVG, 56 TD

Bottom line: Dez Bryant had a problem with maturity when coming out of college, so the Cowboys included stipulations in his contract that he had to abide by. These included:

A midnight curfew
No alcohol
Biweekly counseling sessions
A strip club ban unless approved by the team

Bryant was 21 when he signed this deal, but you would have never known it by the contract provisions. You have to give credit to the Cowboys for being proactive in protecting one of their star players.

But in 2015, they resigned him to a five-year, $70 million deal, which might even be a worse deal than Bryant’s rookie contact. That’s because the Cowboys cut him in 2018 due to disciplinary reasons.

96. Todd MacCulloch

What were the Nets thinking? Bill Kostroun / AP Photo

Sport: Basketball (NBA)

Year: 2001

Contract: 6 years, $34 million

Team: New Jersey Nets

Return on investment: 62 G, 9.7 PPG, 6.1 RPG, 1.4 BPG

Bottom line: When backup center Todd MacCulloch heard that he was offered a $34 million contract by the Nets, he thought it was a prank. Do we need to say anymore?

The offer was real, but the only joke was the contract itself. MacCulloch played one season with the Nets before they realized it was also a joke, and they traded him away.

95. Kevin Brown

Kevin Brown pitched five seasons with the Dodgers before being traded. John Hayes / AP Photo

Sport: Baseball (MLB)

Year: 1999

Contract: 7 years, $105 million

Team: Los Angeles Dodgers

Return on investment: 137 G, 58-32 (.644 W-L%), 2.83 ERA

Bottom line: Kevin Brown’s deal was the first $100 million contract in baseball history, and the Dodgers were the only ones offering anything close to that much money.

The next-highest offer was some $40 million cheaper than L.A.’s offer, and on top of that, Brown’s deal came with perks.

Included were 12 round-trip charter flights from Georgia to Los Angeles so Brown’s family could come to watch him pitch in person.

94. Horace Grant

Horace Grant may have cost the Magic a shot a keeping Shaq. Chris O’Meara / AP Photo

Sport: Basketball (NBA)

Year: 1996

Contract: 5 years, $50 million

Team: Orlando Magic

Return on investment: 193 G, 11.4 PPG, 8.1 RPG, 2.2 APG

Bottom line: The two highest-paid NBA players from 1996 to 1998 were: 1. Michael Jordan and 2. Horace Grant.

The spectacled big man negotiated a front-loaded contract extension in which nearly 60 percent of his total money was paid out in the first two years of the deal.

Just weeks after this deal, Shaquille O’Neal departed Orlando for the Lakers, in part, because the Magic couldn’t match the Lakers’ offer.

93. Willie Taggart

Willie Taggart had a .429 winning percentage at Florida State. Chris Seward / AP Photo

Sport: Football (NCAA)

Year: 2018

Contract: 6 years, $30 million

Team: Florida State

Return on investment: 21 G, 9-12 record (.429 W-L%)

Bottom line: Florida State didn’t just fire Willie Taggart after less than two seasons as head coach. They had to write three checks to get rid of him.

First, they owed Taggart $18 million per the terms of their buyout with him. Then, they owed Taggart’s former team Oregon $3 million since that’s what they agreed to pay to nab him from the Pacific Northwest. But Oregon took Taggart from South Florida, so FSU then had to pay an additional $1.3 million to their fellow Sunshine State school.

In the end, Florida State had to pay out over $20 million to their ex-coach and his two ex-schools.

92. Eddie Gaedel

Now, that’s a small strike zone. AP Photo

Sport: Baseball (MLB)

Year: 1951

Contract: 1 game, $100

Team: St. Louis Browns

Return on investment: Walked in his one career plate appearances to give him the highest on-base percentage in MLB history.

Bottom line: Standing 3-feet-7, Eddie Gaedel was a novelty act and the shortest player in MLB history. He was used as a publicity stunt by Browns owner Bill Veeck, who was just as much a promoter as an owner.

While the $100 wage didn’t impact the Browns much, the reaction to the stunt didn’t sit well in MLB’s offices. They voided Gaedel’s contract afterward and accused Veeck of making a mockery of the game, only to later reinsert Gaedel’s one at-bat into the record books.

91. Nnamdi Asomugha

Nnamdi Asomugha retired in 2013. Lynne Sladky / AP Photo

Sport: Football

Year: 2011

Contract: 5 years, $60 million ($25 million guaranteed)

Team: Philadelphia Eagles

Return on investment: 32 G, 95 TKL, 4 INT, 0 FF

Bottom line: The Eagles signed Nnamdi Asomugha because he was both a great player and a great leader. But after a disastrous first season in Philadelphia, Asomugha spent much of the following season eating lunch in his car instead of with his teammates.

Many people have likely done this at some point in their careers, but those same people likely aren’t working a job where cohesion is of the utmost. Those same people also likely didn’t get $25 million to play a game like football.

Asomugha didn’t last long in Philly and was cut after that second season.

90. Brock Osweiler

Brock Osweiler lasted one season with the Houston Texans. Eric Gay / AP Photo

Sport: Football

Year: 2016

Contract: 4 years, $72 million ($37 million guaranteed)

Team: Houston Texans

Return on investment: 15 G, 15 TD, 16 INT, 59.0 CMP%, 72.2 RAT

Bottom line: Brock Osweiler was so bad in his one year in Houston that the Texans decided to pay to get rid of him rather than pay him.

They traded him to the Browns, but in order to do so, they also had to send a high draft pick just for Cleveland to accept the deal.

This was considered one of the most creative trades in NFL history and only someone of Osweiler’s incompetence could make it happen.

89. Ilya Bryzgalov

Doh. Tom Mihalek / AP Photo

Sport: Hockey (NHL)

Year: 2011

Contract: 9 years, $51 million

Team: Philadelphia Flyers

Return on investment: 99 GM, .905 SV%, 3.09 GAA

Bottom line: Before the Flyers could even get Ilya Bryzgalov’s contract under their salary cap, they first had to trade away two of their best players. Then came this deal, which was an unmitigated disaster that the Flyers bought out just two years into the planned nine years.

But in order to buy out Bryzgalov, the Flyers had to exercise a provision that paid him two-thirds of the remaining money spread out over twice as long as the remaining years.

Thus, Philadelphia is on the hook for $23 million to Bryzgalov to be paid over 14 seasons or until 2027.

88. Bret Hart

Bret Hart was a fan favorite. Wikimedia Commons

Sport: Wrestling

Year: 1997

Contract: 3 years, $7.5 million

Promotion: WCW

Return on investment: Seven-time champion, two-time heavyweight champion

Bottom line: After the Montreal Screwjob in WWF, Bret Hart joined WCW on a fully guaranteed contract. Not only was he making a base of $2.5 million per year, but he also received $6,500 per live event and was guaranteed at least 125 of those events per year.

That comes out to over $800,000 per year if he worked the bare minimum. Additionally, Hart had a reimbursement for disability clause in his deal worth up to $100,000 if he suffered any in-ring injuries, which is a certainty for any professional wrestler.

Of course, injuries derailed Hart’s career, and the deal still makes no sense.

87. Pablo Sandoval

The Red Sox regretted their deal with Pablo Sandoval almost from Day 1. Carlos Osorio / AP Photo

Sport: Baseball (MLB)

Year: 2015

Contract: 5 years, $90 million

Team: Boston Red Sox

Return on investment: 161 G, .237 AVG, 14 HR, 59 RBI

Bottom line: When Pablo Sandoval showed up in Boston looking like this, the locals had a sense things would not go well. He ate himself out of the lineup and eventually out of Boston, who cut bait after two-and-a-half years.

But a contract is a contract, and that meant the team had to continue paying him even though he wasn’t on the team.

Sandoval left Boston in the middle of 2017, and they’ve paid him roughly $40 million since then in salary and with an option buyout.

86. Andrea Pirlo

Andrea Pirlo was not worth the money for New York City FC. Jason DeCrow / AP Photo

Sport: Soccer (MLS)

Year: 2015

Contract: 3 years, $14.1 million

Team: New York City FC

Return on investment: 60 GM, 1 G, 11 AST

Bottom line: Some moves are made to help on the field. Others are made to help in the stands. Signing Pirlo was clearly the latter.

The Italian legend was brought over to New York from Europe due to the city having a large Italian population.

Well, Pirlo helped fill the seats for NYCFC, but he didn’t fill the back of the net with the soccer ball.

85. Nick Foles

Nick Foles played four games with the Jaguars. Stephen B. Morton / AP Photo

Sport: Football (NFL)

Year: 2019

Contract: 4 years, $88 million ($45.1 million guaranteed)

Team: Jacksonville Jaguars

Return on investment: 4 G, 3 TD, 2 INT, 65.8 CMP%, 84.6 RAT

Bottom line: NFL contracts are always loaded with many different bonuses, and Nick Foles’ deal enabled him to take in $30.5 million in the 2019 season.

He received a $25 million signing bonus to go along with his $5 million salary. He also received a $250,000 roster bonus and another $250,000 workout bonus.

Foles’ 2019 earnings of $30.5 million were just a notch lower than the $31.9 million he made in his first seven NFL seasons combined. He got all that for four games of work with the Jaguars.

84. Rusney Castillo

Rusney Castillo has played 162 games in his major league career. Keith Srakocic / AP Photo

Sport: Baseball (MLB)

Year: 2014

Contract: 7 years, $72.5 million

Team: Boston Red Sox

Return on investment: 99 G, .262 AVG, 7 HR, 35 RBI

Bottom line: The way MLB payrolls work is that a player like Rusney Castillo receives his full salary regardless if he’s on the big league club or down in the minors.

But the Red Sox have elected to banish Castillo in the minors in order to avoid the luxury tax they would incur by having Castillo and his salary on their major league books.

So even though Castillo has impressed at the minor league level — and has warranted a callup to the majors — the Red Sox won’t promote him for purely financial reasons.

83. Mike Vanderjagt

Mike Vanderjagt brought little to Dallas. Matt Slocum / AP Photo

Sport: Football (NFL)

Year: 2006

Contract: 3 years, $4.5 million ($2.5 million guaranteed)

Team: Dallas Cowboys

Return on investment: 10 G, 13 FGM, 18 FGA, 72.2 FG%

Bottom line: For years, the Cowboys saved on money by not paying a premium for kickers and applying the money elsewhere.

That philosophy changed in 2006, but they soon regretted doing so as Mike Vanderjagt couldn’t make kicks, couldn’t stay healthy and couldn’t get on the good side of his head coach.

He lasted three months into his three-year deal before being released.

82. Vin Baker

Vin Baker played only 210 games with the Sonics after signing a seven-year deal. Elaine Thompson / AP Photo

Sport: Basketball (NBA)

Year: 1999

Contract: 7 years, $86 million

Team: Seattle SuperSonics

Return on investment: 210 G, 14.3 PPG, 6.6 RPG, 0.8 BPG

Bottom line: Vin Baker was an All-Star in 1998 and then became an alcoholic in 1999. That led to his worst season, but Seattle ignored the warning signs and offered him a massive contract.

Baker’s battles with alcoholism continued to get worse as did his production, and at one point, he even believed drinking would somehow help his free-throw percentage.

It would be another couple of years before he sought help with an alcohol treatment program, and that only came after a coach smelled alcohol on his breath during practice.

81. Carl Pavano

Carl Pavano pitched in only 26 games with the Yankees. John Froschauer / AP Photo

Sport: Baseball (MLB)

Year: 2005

Contract: 4 years, $39.95 million

Team: New York Yankees

Return on investment: 26 G, 9-8 (.529 W-L%), 5.00 ERA

Bottom line: Injuries are a part of the game, but how long a player sits out due to injury is often a matter of toughness. Carl Pavano suffered injury after injury during his four seasons in New York, and his toughness and image took a hit from his teammates.

He pitched the equivalent of one full season yet got paid for four seasons, and Pavano even admitted that he needed to earn the respect of his teammates.

That never happened, and he didn’t become healthy until he left the Big Apple.

80. Phil Jackson

Phil Jackson could not bring an NBA title to the Knicks as an executive. Richard Drew / AP Photo

Sport: Basketball

Year: 2014

Contract: 5 years, $60 million

Team: New York Knicks

Return on investment: 261 G, 90-171 record (.345 W-L%), 0 postseason appearances

Bottom line: Phil Jackson was out of the NBA for three years and never held any front-office experience when the Knicks made him their chief decision-maker as president of basketball operations.

Jackson won 11 titles as a coach but seemed out of touch with the contemporary basketball landscape, and the Knicks set a franchise record for most single-season losses under him.

He lasted three years into his five-year deal before the Knicks parted ways with him in 2017.

79. DeAngelo Hall

DeAngelo Hall, left, played eight games with the Raiders. Tony Avelar / AP Photo

Sport: Football (NFL)

Year: 2008

Contract: 7 years, $70 million ($24.5 million guaranteed)

Team: Oakland Raiders

Return on investment: 8 G, 48 TKL, 3 INT, 0 FF

Bottom line: Not only did the Raiders sign Hall to this monstrous contract, but they also traded away a high draft pick in order to get him, before signing him.

After poor play in half a season, the Raiders asked him to restructure the deal, but Hall declined. As a result, they released him and ended up paying Hall $8 million total ($7 million signing bonus plus $1 million salary) for eight games of play.

78. Shea Weber

How would like to be the player that caused an NHL lockout? Mark Humphrey / AP Photo

Sport: Hockey (NHL)

Year: 2012

Contract: 14 years, $110 million

Team: Nashville Predators

Return on investment: 283 GP, 67 G, 113 A, 180 PTS

Bottom line: The NHL had a lockout during the 2012-13 season that cost the league 510 regular-season games. One of the biggest reasons for that lockout was Shea Weber’s deal and specifically the 14-year length of it.

During the lockout, both the players and owners agreed to a new rule in which eight years would be the maximum length of a contract to prevent similar mistakes as Weber’s deal with the Predators.

77. Melvin Upton Jr.

Melvin Upton Jr. hit .198 with the Braves. David Goldman / AP Photo

Sport: Baseball (MLB)

Year: 2013

Contract: 5 years, $75.25 million

Team: Atlanta Braves

Return on investment: 267 G, .198 AVG, 21 HR, 61 RBI

Bottom line: In the 2013 offseason, the Braves acquired Melvin Upton and his brother Justin.

They spent more for Melvin but got much better production out of Justin, so in a way, you could argue that the Braves broke even with the Uptons.

But the only notable thing Melvin did in his time in Atlanta was pose for a Sports Illustrated cover alongside Justin and their “long-lost cousin” Kate Upton.

76. Mike Hampton

Mike Hampton went 21-28 with the Rockies. Erik S. Lesser / AP Photo

Sport: Baseball (MLB)

Year: 2001

Contract: 8 years, $121 million

Team: Colorado Rockies

Return on investment: 62 G, 21-28 (.429 W-L%), 5.75 ERA

Bottom line: When Mike Hampton signed the largest contract in MLB history at the time, he angered many media members with his comments about why he left the New York Mets for the Colorado Rockies.

Hampton cited Colorado’s “school system” as the reason why he went to Colorado, which insulted the intelligence of everyone who knew he left for $121 million.

75. Jay Cutler

Jay Cutler was not Mr. Popular in Chicago. Charles Rex Arbogast / AP Photo

Sport: Football (NFL)

Year: 2014

Contract: 7 years, $126 million ($54 million)

Team: Chicago Bears

Return on investment: 35 G, 53 TD, 34 INT, 64.5 CMP%, 88.9 RAT

Bottom line: More so than any position in sports, you want your quarterback to have great leadership skills, motivate teammates and project confidence. With that in mind, Jay Cutler should have been playing any position besides quarterback.

He had teammates call out his leadership and question his heart, which is something an organization doesn’t want to hear about a guy they signed to a nine-figure deal.

As for projecting confidence, Cutler was known for being the King of Bad Body Language.

74. David Wright

New York Mets’ David Wright high-fives with teammates in the dugout after scoring on a double hit by Daniel Murphy against the Miami Marlins in the third inning of a baseball game at Citi Field on Friday, April 25, 2014, in New York. Kathy Kmonicek / AP Photo

Sport: Baseball (MLB)

Year: 2013

Contract: 8 years, $138 million

Team: New York Mets

Return on investment: 323 G, .279 AVG, 38 HR, 152 RBI

Bottom line: Eight years in MLB translates to 1,296 games. Since David Wright took the field for just 323 games during that span, due to injuries, he only played in 25 percent of the possible games.

You see why so many kids want to be pro athletes when they grow up. They can get paid $138 million for showing up to work just 25 percent of the time.

73. LeCharles Bentley

LeCharles Bentley never played a game for the Browns. Ron Schwane / AP Photo

Sport: Football (NFL)

Year: 2006

Contract: 6 years, $35 million ($12.5 million guaranteed)

Team: Cleveland Browns

Return on investment: 0 games

Bottom line: This contract was more bad luck than anything else as LeCharles Bentley suffered a season-ending injury on the first play of the first practice. He underwent four surgeries and had a virus so bad that doctors discussed possible amputation of his lower leg.

Bentley missed two full years due to injury and never suited up for the Browns but still collected $15 million to essentially get operated on and rehab.

72. Nicolas Batum

Nicolas Batum, left, got paid star money for role-player production. Nell Redmond / AP Photo

Sport: Basketball (NBA)

Year: 2016

Contract: 5 years, $120 million

Team: Charlotte Hornets

Return on investment: 238 G, 11.3 PPG, 5.4 RPG, 4.7 APG

Bottom line: Thanks to a new TV deal, the NBA’s salary cap hiked in 2016 as it jumped $24 million after increasing to just $7 million in 2015. Players like Nicolas Batum were the beneficiaries. Since they weren’t necessarily worth substantial raises, they simply became free agents at the right time.

The worst part of Batum’s deal for the Hornets is that his contract contains a player option for the 2020-21 season. Batum accepted the $27 million for the year.

Why take his chances on the open market? Not even the biggest gambler would take that risk.

71. Grant Hill

Injuries limited Grant Hill with the Magic. Gregory Smith / AP Photo

Sport: Basketball (NBA)

Year: 2000

Contract: 7 years, $92.8 million

Team: Orlando Magic

Return on investment: 200 G, 16.4 PPG, 5.0 RPG, 3.1 APG

Bottom line: The Orlando Magic’s medical staff takes the blame on this one since Grant Hill had a preexisting ankle injury that they overlooked before signing him.

He then had to endure multiple surgeries as well as a potentially fatal staph infection that put him on antibiotics for six months. All of these injuries then affected his gait and led to groin injuries, which resulted in hernia surgery.

As a result of his medical issues, Hill played in 200 games for Orlando and missed 374 games due to injury.

70. Juan Gonzalez

Juan Gonzalez, center, did not finish his career with a bang. Ron Schwane / AP Photo

Sport: Baseball (MLB)

Year: 2005

Contract: 1 year, $600,000

Team: Cleveland Indians

Return on investment: 1 G, 0-for-1

Bottom line: Employers always want their employees to put in extra effort for the greater good of an organization. Well, Juan Gonzalez put in extra effort, and it cost the Indians’ organization $600,000.

He ran out a groundball during his one at-bat and ended up tearing his hamstring. The play would be the last of his career, but he won’t complain about the $600,000 he earned for one day of work.

69. Steve Spurrier

Steve Spurrier, center, did not have much success in Washington, D.C. Koji Sasahara / AP Photo

Sport: Football (NFL)

Year: 2002

Contract: 5 years, $25 million

Team: Washington Football Team (formerly Redskins)

Return on investment: 32 G, 12-20 record (.375 W-L%)

Bottom line: Steve Spurrier was that guy who took over a new company and fired many of the longtime employees so he could bring in his old co-workers. That usually doesn’t work in the corporate world, and it also didn’t work in the football world.

He later admitted that he joined the Washington Football Team (then the Redskins) for all of the wrong reasons and that he went to D.C. because “they offered the most money.”

68. Kobe Bryant

Kobe Bryant played 1,346 games in the NBA. Lenny Ignelzi / AP Photo

Sport: Basketball (NBA)

Year: 2014

Contract: 2 years, $48.5 million

Team: Los Angeles Lakers

Return on investment: 101 G, 19.2 PPG, 4.4 RPG, 3.8 APG

Bottom line: Despite being 35 years old and coming off a torn Achilles’ tendon, Kobe Bryant was awarded with a contract that kept him as the league’s highest-paid player.

The Lakers were slammed for the deal since they seemed to be rewarding past accomplishments instead of future success.

But Bryant was still a box-office draw for Lakers fans even though he struggled to stay healthy during the deal, including suffering a leg fracture and torn rotator cuff.

67. Nathan Horton

Nathan Horton hears cash registers ringing. Jay LaPrete / AP Photo

Sport: Hockey (NHL)

Year: 2013

Contract: 7 years, $37.1 million

Team: Columbus Blue Jackets

Return on investment: 36 GM, 5 G, 5 AST, 19 PTS

Bottom line: Nathan Horton was considered an injury-prone player even before he signed this deal, and he didn’t suddenly become an Iron Man afterward.

He had surgery shortly after signing the contract and then was diagnosed with a degenerative back injury after his only season in Columbus.

The worst part of this deal from the Blue Jackets’ standpoint is that Horton’s contract wasn’t insured, leaving them on the hook even if he was unable to play due to injury.

66. Barry Zito

Barry Zito won less than 45 percent of his games with the Giants. Julie Jacobson / AP Photo

Sport: Baseball (MLB)

Year: 2007

Contract: 7 years, $126 million

Team: San Francisco Giants

Return on investment: 208 G, 63-80 (.441 W-L%), 4.62 ERA

Bottom line: Barry Zito’s contract was worth $126 million, but he made $133 million during his time in San Francisco. That’s because the Giants had a team option in the eighth season for $18 million or a buyout option for $7 million.

Due to how poorly Zito performed in San Francisco, the team elected to pay him the $7 million to go away rather than paying $18 million for another season of subpar results.

65. CM Punk

CM Punk went 0-2 in the UFC, but he still was a big winner in the octagon with his contract. David Dermer / AP Photo

Sport: Mixed Martial Arts

Year: 2014

Contract: 2 fights, $1.5 million

Team: N/A

Return on investment: 0-2 record

Bottom line: Wrestler-turned-mixed martial artist CM Punk was a total failure in the octagon. But his agent certainly didn’t fail his client — he negotiated Punk to receive a pair of $500,000 purses for each of his fights.

Punk got that just for showing up, whether he won or lost, and then he received a cut of the pay-per-view revenue, which pushed him over seven figures.

If you do the math, Punk made $80,000 for every minute he lasted in the octagon and $1,333.33 for every second.

64. Charlie Kerfeld

There’s a reason Charlie Kerfeld isn’t a household name. bubbaonbaseball / Twitter

Sport: Baseball (MLB)

Year: 1987

Contract: 1 year, $110,037.37 plus 37 boxes of Jell-O

Team: Houston Astros

Return on investment: 21 G, 0-2 record, 6.67 ERA

Bottom line: Charlie Kerfeld wore No. 37, which is why he asked for an extra $37, an extra 37 cents and an extra 37 boxes of Jell-O in his contract.

Perhaps he ate all 37 boxes in one sitting since Kerfeld battled weight problems throughout the 1987 season with the Astros and was banished to the minors.

63. Chuck Smith

Chuck Smith, No. 91, never got healthy enough to contribute to the Panthers. Chuck Burton / AP Photo

Sport: Football (NFL)

Year: 2000

Contract: 5 years, $21 million ($4.5 million guaranteed)

Team: Carolina Panthers

Return on investment: 2 G, 1 TKL, 0 SACK, 0 FF

Bottom line: The Panthers deserve all of the blame for this contract. They didn’t do their due diligence on Chuck Smith’s medical. It also should have been a sign that his previous team didn’t make much of an effort to re-sign him, despite Smith being productive.

He had an arthritic knee before he signed the deal, but Carolina was too blinded by his production instead of paying attention to his medical report.

He played just a handful of snaps for Carolina, had another surgery and then failed his physical before retiring.

62. Josh Smith

Josh Smith never found a comfort zone in Detroit. Danny Johnston / AP Photo

Sport: Basketball (NBA)

Year: 2013

Contract: 4 years, $54 million

Team: Detroit Pistons

Return on investment: 105 G, 15.5 PPG, 6.9 RPG, 3.7 APG

Bottom line: Sometimes sports franchises get too overconfident in their abilities and try to fit a square peg in a round hole. That’s the case with Josh Smith, who was a good player but was forced to play out of position for the Pistons.

Eighteen months into a four-year contract, and the Pistons realized the error of their ways and decided they’d be better off paying Smith not to play for them rather than play for him.

So they cut him.

61. Jake Delhomme

The NFL stood for Not For Long for Jake Delhomme. Rick Havner / AP Photo

Sport: Football (NFL)

Year: 2009

Contract: 5 years, $42.5 million ($20 million guaranteed)

Team: Carolina Panthers

Return on investment: 11 G, 8 TD, 18 INT, 55.5 CMP%, 59.4 RAT

Bottom line: Imagine having your worst day at work, ever, and then being rewarded with a pay raise. That’s what happened to Jake Delhomme, who committed six turnovers in a playoff loss and then got a new contract just weeks later.

Weeks is also how long his “four-year contract” with the Panthers lasted as that six-turnover game wasn’t an anomaly, and Delhomme lasted just one season.

60. Jim Harbaugh

Will Jim Harbaugh ever lead Michigan to a national title? Darron Cummings / AP Photo

Sport: Football (NCAA)

Year: 2015

Contract: 7 years, $52 million

Team: Michigan Wolverines

Return on investment: 69 G, 48-21 record (.696 W-L%)

Bottom line: Jim Harbaugh is a very good college coach, but Michigan is paying him to be a great coach.

His contract contains numerous bonuses, perks and incentives such as the use of two university-provided vehicles and a private suite for games that accommodates 16 people. Michigan also makes an annual $2 million payment to Harbaugh’s life insurance premium, and he gets $4,000 in annual apparel allowance.

Yes, an NCAA coach on a $52 million contract gets an allowance.

59. Larry Brown

Larry Brown was not an MVP player with the Raiders the way he was with the Cowboys. Susan Ragan / AP Photo

Sport: Football (NFL)

Year: 1996

Contract: 5 years, $12.5 million ($3.5 million guaranteed)

Team: Oakland Raiders

Return on investment: 12 G, 26 TKL, 1 INT, 0 FF

Bottom line: Sometimes players aren’t good fits on the field, and sometimes they’re not good fits off the field. Larry Brown fell into both categories during his short stay in Oakland.

He played in just 12 of 32 games due to poor play, injuries and a suspension for “conduct detrimental to team.” The team didn’t specify what that conduct was but the Raiders soon realized that Brown was hurting them more than helping them.

Thus, they fired him by waiving him two years into a five-year deal.

58. Mo Vaughn

Mo money, more problems for the Angels. Mark J. Terrill / AP Photo

Sport: Baseball (MLB)

Year: 1999

Contract: 6 years, $80 million

Team: Anaheim Angels

Return on investment: 300 G, .276 AVG, 69 HR, 225 RBI

Bottom line: Mo Vaughn’s contract got off to a bad start when he injured his ankle in his first game, which sent him to the disabled list. The contract also had a bad ending since he missed the entire 2001 season after tearing a tendon.

In between, he wasn’t that good for the Angels, and his teammates didn’t shed a tear when he was traded to the Mets in 2002.

After the trade, the Angels’ Troy Percival said, “We may miss Mo’s bat, but we won’t miss his leadership.”

57. Don Nelson

Don Nelson, left, didn’t last one full season with the Knicks. Elaine Thompson / AP Photo

Sport: Basketball (NBA)

Year: 1995

Contract: 3 years, $5 million

Team: New York Knicks

Return on investment: 59 G, 34-25 record (.576 W-L%)

Bottom line: Don Nelson angered so many people in the Knicks organization that they didn’t even give him a full season to do his job.

Despite being a top-three seed, the team fired him with a month left in the regular season. The chief reason was that he wanted to trade Knicks legend Patrick Ewing.

The two sides eventually reached a $3.2 million settlement that allowed Nelson to seek another job without the Knicks requesting additional compensation.

56. Josh Hamilton

Josh Hamilton had a disappointing time on the Angels. Tony Gutierrez / AP Photo

Sport: Baseball (MLB)

Year: 2013

Contract: 5 years, $125 million

Team: Los Angeles Angels

Return on investment: 240 G, .255 AVG, 31 HR, 123 RBI

Bottom line: After Josh Hamilton signed this deal, his former team the Texas Rangers expressed disappointment on how he handled the situation.

Hamilton didn’t give the Rangers a chance to match the Angels’ offer, and instead of calling Texas to tell them what Los Angeles offered, he simply called them after the fact to let them know he was heading west.

After his paltry production, perhaps the Angels were the ones expressing disappointment.

55. Spencer Prior

Spencer Prior produced more entertainment off the field for Cardiff City than on it. Coral / Twitter

Sport: Soccer (Premier League)

Year: 2001

Contract: £700,000 fee ($925,330)

Team: Cardiff City

Return on investment: 81 APP, 2 G, 0 A, 4 YC

Bottom line: Cardiff City’s owner had quite a sense of humor, so he included in Spencer Prior’s contract a clause in which the player had to eat sheep testicles to consummate the deal. Seriously.

Prior was on board to join the club, but in reality, a meal served to Prior that was labeled as sheep testicles was actually just chicken. Prior wasn’t told that fact until after downing the chicken.

But it proved his commitment to the team. Too bad he couldn’t deliver on the field.

54. Javon Walker

Now you see Javon Walker’s production, now you don’t. Paul Sakuma / AP Photo

Sport: Football (NFL)

Year: 2008

Contract: 6 years, $55 million ($16 million guaranteed)

Team: Oakland Raiders

Return on investment: 11 G, 15 REC, 196 YDS, 13.1 AVG, 1 TD

Bottom line: Javon Walker’s time with the Raiders maybe had a bit of foreshadowing. Just three months after signing his contract, he was found unconscious on the Las Vegas Strip.

He was the victim of a robbery, but one could say he then robbed the Raiders of millions of dollars with his lackluster production over two years.

As for the foreshadowing, in 2020, the Raiders relocated to the site of the crime, Las Vegas.

53. Bill Walton

Bill Walton had a forgettable Clippers career. Fred Jewell / AP Photo

Sport: Basketball (NBA)

Year: 1979

Contract: 7 years, $7 million

Team: San Diego Clippers

Return on investment: 249 G, 10.5 PPG, 8.3 RPG, 2.6 APG, 2.0 BPG

Bottom line: After a nasty split to his Trail Blazers career over the way they handled his injuries, Bill Walton signed with the hometown San Diego Clippers.

But a new setting produced the same results, and he played in just 43 percent of the possible games during the length of the deal.

The Clippers struggled so much during Walton’s tenure that they ended up relocating to Los Angeles, and Walton cites that as the biggest failure of his career.

52. Jim McIlvaine

What were the Sonics thinking? Michael Caulfield / AP Photo

Sport: Basketball (NBA)

Year: 1996

Contract: 7 years, $33.6 million

Team: Seattle SuperSonics

Return on investment: 160 G, 3.5 PPG, 3.7 RPG, 1.9 BPG

Bottom line: Not only was this a bad signing in terms of production from Jim McIlvaine, but it was a bad signing for team morale and chemistry.

McIlvaine got a huge contract while one of the team’s stars, Shawn Kemp, had his contract demands rejected by the team.

Kemp eventually got a pay raise — from a new team after being traded — and that was the beginning of the end of pro basketball in Seattle.

51. Todd Gurley

Todd Gurley gets paid by the Rams while playing for another team. Jason Behnken / AP Photo

Sport: Football (NFL)

Year: 2018

Contract: 4 years, $57.5 million ($45 million guaranteed)

Team: Los Angeles Rams

Return on investment: 29 G, 2,108 YDS, 29 TD, 4.4 AVG

Bottom line: The weird thing about this contract was that it was an extension signed in 2018, but it didn’t go into effect until 2020.

Todd Gurley still had two years left on his rookie deal. But the Rams cut Gurley before the 2020 season, so he didn’t play a single game under this deal.

However, guaranteed money is guaranteed money, and the Rams will have to pay him while he suits up for another team.

50. David Boston

David Boston tested positive for steroids in San Diego. TheClemReport / Twitter

Sport: Football (NFL)

Year: 2003

Contract: 7 years, $47 million ($12 million guaranteed)

Team: San Diego Chargers

Return on investment: 14 G, 70 REC, 880 YDS, 7 TD, 12.6 AVG

Bottom line: When David Boston showed up in San Diego with arms like this, there were suspicions that he was on something illegal. He then refused to lose weight at the team’s request and was suspended after arguing with the team’s strength and conditioning coach.

His abrasive personality continued to rub teammates and coaches the wrong way, and his production didn’t come close to matching his salary.

So Boston was traded away just one year into the contract and, to the surprise of no one, a receiver who looked like this tested positive for steroids and was hit with a four-game suspension.

49. Alonzo Mourning

Alonzo Mourning only played 30 games with the Nets due to kidney diseases. Bill Kostroun / AP Photo

Sport: Basketball (NBA)

Year: 2003

Contract: 4 years, $22 million

Team: New Jersey Nets

Return on investment: 30 G, 9.4 PPG, 5.1 RPG, 1.6 BPG

Bottom line: Due to various kidney diseases, Alonzo Mourning played in just 88 of 246 games from 2000 to 2003. But the Nets treated this disease like a sprained ankle and thought he would be able to bounce back without issue.

So they signed him to a four-year deal in July 2003, and just four months later Mourning announced his retirement to undergo a kidney transplant.

This was a lesson learned for the Nets and all NBA teams that you can’t view organ diseases the same as orthopedic injuries.

48. Mike Tyson

Mike Tyson, right, lost a lot of money to Don King. AP Photo

Sport: Boxing

Year: 1988

Contract: Don King to receive 30 percent of Tyson’s purses

Team: N/A

Return on investment: 10-3 (8 KO), Won heavyweight title

Bottom line: Boxing promoter Don King getting 30 percent of Tyson’s purses is just one clause in the horrible contract “Iron Mike” signed when he was the heavyweight champion.

King also got a cut of Tyson’s TV and casino deals, foreign broadcast rights and even owned the boxer’s likeness.

When Tyson appeared in the WWF in 1998, they needed a picture for their ads, and the picture they received had its rights credited to Don King Productions.

47. Kevin Garnett

Kevin Garnett’s $126 million deal with the Timberwolves was bad for the NBA. Ann Heisenfelt / AP Photo

Sport: Basketball (NBA)

Year: 1998

Contract: 6 years, $126 million

Team: Minnesota Timberwolves

Return on investment: 454 G, 22.5 PPG, 12.3 RPG, 5.1 APG, 1 MVP

Bottom line: This was a great deal for Minnesota since they were a small market who locked up an MVP on a long-term deal. It was an even better deal for Garnett because $126 million can’t be a bad thing. But this was a terrible contract for the NBA as a whole as KG’s deal set a bad precedent for other players.

After the deal, every above-average player wanted an eight-figure deal, and this contract played a big role in the ensuing NBA lockout in 1998-99 season.

46. Ken Griffey Jr.

Ken Griffey Jr. had a disappointing homecoming with the Reds. Al Behrman / AP Photo

Sport: Baseball (MLB)

Year: 2000

Contract: 9 years, $112.5 million

Team: Cincinnati Reds

Return on investment: 945 G, .270 AVG, 210 HR, 602 RBI

Bottom line: No one could have seen this disaster of a contract coming as Ken Griffey returned to Cincinnati, which is where he grew up.

But perhaps The Kid feasted a little too much on home-cooking because he got fat and lazy while in The Queen City. Being out of shape often led to injuries and then a subpar work ethic led to longer-than-normal rehabs.

The Reds gleefully declined a $16 million club option that could have brought Griffey back for a 10th season in 2009.

45. Bobby Petrino

Louisville made a terrible deal with Bobby Petrino, center. Michael Dwyer / AP Photo

Sport: Football (NCAA)

Year: 2016

Contract: 7 years, $31.7 million

Team: Louisville Cardinals

Return on investment: 36 G, 19-17 record (.528 W-L%)

Bottom line: While college athletes continue to bring in their schools millions of dollars and see none of it, coaches like Bobby Petrino continue to make out like bandits after being fired.

When he signed a contract extension with Louisville, the deal had several buyout provisions that were in Petrino’s favor. The coach didn’t even last three years into his seven-year deal, but Louisville was still forced to pay him the remaining guaranteed money on his contract.

So on the day that Petrino found out he was fired, he couldn’t be too upset. That also meant he would be getting over $14 million thanks to Louisville negotiating a terrible deal.

44. Rick DiPietro

Rick DiPietro got a lot of money from the Islanders. David Duprey / AP Photo

Sport: Hockey (NHL)

Year: 2006

Contract: 15 years, $67.5 million

Team: New York Islanders

Return on investment: 175 GP, 72-74 record, .904 SV%, 2.89 GAA

Bottom line: Rick DiPietro’s deal is believed to be the second-longest in North American team sports history, trailing only Magic Johnson’s 25-year deal with the Lakers. But DiPietro was no Magic on the ice, and seven years into the deal, the Islanders wanted out.

The two sides agreed to a buyout, and DiPietro was waived, but he still received two-thirds of the $36 million he was due.

The money is being paid out in eight annual installments of $1.5 million per year until 2021.

43. Jayson Williams

Jayson Williams’ NBA career ended in 1999. Duane Burleson / AP Photo

Sport: Basketball (NBA)

Year: 1998

Contract: 7 years, $100 million

Team: New Jersey Nets

Return on investment: 30 G, 8.1 PPG, 12.0 RPG, 2.0 BPG

Bottom line: Jayson Williams suffered a career-ending injury just 30 games after signing for seven figures, but that was just the tip of the iceberg for the problems he would endure.

In 2002, he accidentally shot and killed his limo driver while playing with a gun. Then, while on trial, he was arrested multiple other times, including for a DWI and a bar fight.

He was sentenced to five years in jail but ended up serving just over two years, and all of the money spent on a defense team caused him to nearly go bankrupt.

42. Robert Griffin III

A good deal for Washington was a bad deal for Robert Griffin III. Richard Lipski / AP Photo

Sport: Football (NFL)

Year: 2015

Contract: 1 year, $16.1 million guaranteed

Team: Washington Football Team (formerly Redskins)

Return on investment: DNP

Bottom line: In 2015, the Washington Football Team (then the Redskins) picked up Robert Griffin’s option for the 2016 season worth just over $16 million. But that option was only guaranteed for injury, which meant if he got injured during the 2015 season and that injury caused him to rehab into 2016, then he would be guaranteed the money.

But if Griffin didn’t get hurt, then Washington could later decline the option and not pay anything. Shortly after picking up the option, Washington realized that they didn’t want Griffin for 2016, and the only way they could guarantee he wouldn’t get injured and the option tolling was by not playing him. At all.

A healthy Griffin didn’t play one single snap during the 2015 season to prevent any chance of him getting hurt. It was a smart financial decision by the Redskins but turned out to be a bad deal for Griffin, who essentially had a redshirt year.

41. Blake Griffin

Blake Griffin did not end up being a Clipper for life. Mark J. Terrill / AP Photo

Sport: Basketball (NBA)

Year: 2017

Contract: 5 years, $173 million

Team: Los Angeles Clippers

Return on investment: 33 G, 22.6 PPG, 7.9 RPG, 5.4 APG, 0.3 BPG

Bottom line: In July 2017, the Clippers compared Blake Griffin to Martin Luther King and Gandhi. They told him he would be a Clipper for life, and they held a mock ceremony to raise his jersey to the rafters in order to sell Griffin on re-signing with the team, which he did.

Six months later, they traded him to Detroit with 4.5 years left on his contract. Apart from the business of the NBA smacking Griffin in the face, he hasn’t been able to live up to his contract because he’s constantly injured.

He’s missed over one-third of his team’s possible games but still gets 100 percent of the money on his contract.

40. Matt Flynn

Matt Flynn didn’t do much in Seattle, and he still made millions of dollars. Rick Bowmer / AP Photo

Sport: Football (NFL)

Year: 2012

Contract: 3 years, $20.5 million ($9 million guaranteed)

Team: Seattle Seahawks

Return on investment: 3 G, 0 TD, 0 INT, 9 ATT

Bottom line: If you do the math, Matt Flynn made $1 million for every pass he threw in Seattle.

That’s what happens when you lose the starting job to some rookie named Russell Wilson and have to serve as his backup.

For comparison, Wilson made just over $1 million during the 2012 season, which comes out to $2,568.45 for every pass he threw that year.

39. Percy Harvin

Percy Harvin was not a good teammate on the Seahawks. Ted S. Warren / AP Photo

Sport: Football (NFL)

Year: 2013

Contract: 6 years, $67 million ($25.5 million guaranteed)

Team: Seattle Seahawks

Return on investment: 6 G, 23 REC, 150 YDS, 0 TD, 6.5 AVG

Bottom line: Forget about the multiple injuries and poor production. What makes Percy Harvin’s deal so terrible is that he was a locker-room cancer in Seattle.

There were times where he refused to enter into a game, and there were also times in which he punched teammates in the face.

Right, Golden Tate?

38. Glenn Robinson

Glenn Robinson got a $68 million deal as an NBA rookie. Morry Gash / AP Photo

Sport: Basketball (NBA)

Year: 1994

Contract: 10 years, $68 million

Team: Milwaukee Bucks

Return on investment: 679 G, 20.8 PPG, 6.1 RPG, 2.8 APG

Bottom line: After holding out for a 13-year, $100 million deal, Glenn Robinson settled for just $68 million over a decade. It remains the largest contract ever given to a rookie as Robinson was the No. 1 overall pick in 1994 after a standout career at Purdue.

The NBA quickly realized that they couldn’t be handing out these massive deals to unproven rookies, so the next season they implemented rookie-scale contracts that have predetermined amounts based on a player’s draft spot.

37. Joakim Noah

Joakim Noah has six words to say: Thank you, NBA collective bargaining agreement. Nick Wass / AP Photo

Sport: Basketball (NBA)

Year: 2016

Contract: 4 years, $72 million

Team: New York Knicks

Return on investment: 53 G, 4.6 PPG, 7.9 RPG, 2.0 APG, 0.7 BPG

Bottom line: During Joakim Noah’s brief stay in New York, he failed a drug test, got suspended, had a verbal exchange with his coach and produced subpar on-court results. Besides that, everything was great.

The Knicks gave up on him after two years but will still have to pay him until 2022 thanks to the NBA’s collective bargaining agreement.

36. Ville Leino

Ville Leino did not enjoy playing in Buffalo. Alan Diaz / AP Photo

Sport: Hockey (NHL)

Year: 2011

Contract: 6 years, $27 million

Team: Buffalo Sabres

Return on investment: 137 GP, 10 G, 36 A, 46 PTS

Bottom line: “Jail.” That’s how Ville Leino described what it was like playing in Buffalo. He said there was pressure on him, and he had no way out of it.

He said he just got up every morning and unemotionally went to work just how an inmate goes through the motions of whatever they have to do that day.

Leino’s “sentence” was supposed to last six years, but he was released — both literally and figuratively — less than halfway into his term.

35. David Beckham

David Beckham got a great deal when he joined MLS. Jeremy Piper / AP Photo

Sport: Soccer (MLS)

Year: 2007

Contract: 5 years, $32.5 million

Team: Los Angeles Galaxy

Return on investment: 98 GM, 18 G, 31 AST

Bottom line: At the time, this was a good deal for the MLS to raise its profile by landing the world’s most famous soccer player. But then it was revealed that David Beckham had a special ownership provision in the deal, which enabled him to make off like a bandit when he exercised that option and made this a bad deal for MLS.

In this contract, Beckham was given the option to purchase an MLS expansion team for $25 million. That was the range of what a team went for in 2007, but now some teams are worth $500 million.

Beckham exercised his option in 2014 and bought into the ownership group of Inter Miami CF at a much cheaper price than his fellow co-owners.

34. Samuel Eto’o

Samuel Eto’o scored with his Anzhi Makhachkala deal. The team? Not so much. Jon Super / AP Photo

Sport: Soccer (Russian Professional Football League)

Year: 2011

Contract: 3 years, $87 million

Team: Anzhi Makhachkala

Return on investment: 73 GM, 36 G, 11 AST

Bottom line: Russian club Anzhi Makhachkala made Samuel Eto’o this offer with the hope of raising their profile as an elite club.

Well, that didn’t happen, but it did raise the Cameroon star’s bank account since he made twice as much as Cristiano Ronaldo did with Real Madrid.

But besides the salary, the best part of Eto’o’s contract was that Anzhi reportedly paid his rent in Russia, which checked in at $80,000 per month.

33. Chandler Parsons

Chandler Parsons played only 95 games for the Grizzlies. David Zalubowski / AP Photo

Sport: Basketball (NBA)

Year: 2016

Contract: 4 years, $94 million

Team: Memphis Grizzlies

Return on investment: 95 G, 7.2 PPG, 2.6 RPG, 1.8 APG

Bottom line: Chandler Parson had two knee surgeries in one year, but the Grizzlies disregarded his injury history and signed him for nearly $100 million.

Guess what happened right after the deal? Parsons hurt his knee again and never stayed healthy during the duration of his contract. He and the Grizzlies were at odds over his level of play, and the two sides parted ways with Parsons still under contract.

Thus, he simply sat on his couch for months — while still getting paid — until the team found a trade partner in the Atlanta Hawks.

32. Michael Jordan

Michael Jordan made $1.1 million playing minor league baseball. Dave Martin / AP Photo

Sport: Baseball (MiLB)

Year: 1994

Contract: 1 year, $4 million

Team: Chicago White Sox/Birmingham Barons

Return on investment: 127 G, .202 AVG, 3 HR, 51 RBI (minors)

Bottom line: When Michael Jordan retired in 1993 to take up baseball, the team he signed with just happened to be owned by the same man who owned the Chicago Bulls.

Owner Jerry Reinsdorf then decided to pay Jordan his full Bulls salary during his time in minor league baseball. While it was certainly a nice gesture — and Jordan may have shown his gratefulness by returning to the NBA — it also may have upset many MLB players.

The average MLB salary in 1994 was just $1.1 million so someone in the minors making three-and-a-half times that didn’t sit well.

31. Joey Votto

The Reds are paying Joey Votto a lot of money. Gene J. Puskar / AP Photo

Sport: Baseball (MLB)

Year: 2014

Contract: 10 years, $225 million

Team: Cincinnati Reds

Return on investment: 827 G, .298 AVG, 127 HR, 414 RBI

Bottom line: This deal was signed before the 2012 season but didn’t go into effect until two years later and runs through 2023.

Joey Votto turned 30 years old in 2014. That means not a single year of the decade-long deal will takes place during a player’s prime, which is his 20s.

Add in the fact that Votto was given a no-trade clause in the deal, and the Reds are stuck with an albatross of a contract that they can’t get rid of.

30. Sam Bradford

Sam Bradford wasn’t worth the money for the Cardinals. Ralph Freso / AP Photo

Sport: Football (NFL)

Year: 2018

Contract: 2 years, $40 million ($15 million guaranteed)

Team: Arizona Cardinals

Return on investment: 3 G, 2 TD, 4 INT, 62.5 CMP%, 62.5 RAT

Bottom line: In addition to his salary, Sam Bradford had per-game bonuses of $312,500 that he would get for every game that he was active.

Over a 16-game season, that would total up to $5 million, but it took the Cardinals just three games to realize Bradford wasn’t worth the money.

They made him inactive starting with Week 4, so he wouldn’t get the bonuses, and then they released him midseason.

29. Jacoby Ellsbury

Jacoby Ellsbury did not make it in New York the way the Yankees wanted. Kathy Willens / AP Photo

Sport: Baseball (MLB)

Year: 2014

Contract: 7 years, $153 million

Team: New York Yankees

Return on investment: 520 G, .264 AVG, 39 HR, 102 SB

Bottom line: Chances are that a player who’s injury-prone in his 20s will also be injury-prone in his 30s. The Yankees thought Ellsbury would be the exception and defeat Father Time, and they thought wrong.

He missed the entire 2018 and 2019 seasons due to injury but still raked in over $42 million during those seasons to essentially rehab.

You gotta love MLB’s guaranteed contracts.

28. Jerry Porter

Jerry Porter, right, played 10 games with the Jaguars. Phil Coale / AP Photo

Sport: Football (NFL)

Year: 2008

Contract: 6 years, $30 million ($10 million guaranteed)

Team: Jacksonville Jaguars

Return on investment: 10 G, 11 REC, 181 YDS, 1 TD, 16.5 AVG

Bottom line: Jerry Porter’s tenure in Jacksonville started with hamstring surgery, ended with a groin injury and had little in terms of actual football in between. Doing the math, he made $1 million for every game and $10 million for every touchdown.

The Jaguars could have brought him back for just $1 million in salary the following year, but they decided to cut their losses and cut him in 2009.

27. Bruce Sutter

Bruce Sutter rolled the dice on deferred payments with the Braves. And won. DaveSalter_ / Twitter

Sport: Baseball (MLB)

Year: 1985

Contract: 6 years, $9.1 million

Team: Atlanta Braves

Return on investment: 112 G, 40 SV, 4.55 ERA

Bottom line: Bruce Sutter’s deal isn’t extravagant, but he opted to have his money deferred, and the Braves agreed in order to appease the Cy Young winner. But this wasn’t just a four- or five-year deferment but rather a 30-year deferment.

Atlanta is, and will be, paying Sutter no less than $1.12 million per year through 2021. Sutter last pitched in 1988 so he’ll still be receiving checks from the Braves for 33 years after his retirement when he’s 68 years old. And he’ll get the $9.1 million “principal.”

In the end, his deal will be worth over $44 million.

26. Marcell Dareus

You might say Marcell Dareus stole money from the Bills. Bill Wippert / AP Photo

Sport: Football (NFL)

Year: 2016

Contract: 6 years, $96 million ($60 million guaranteed)

Team: Buffalo Bills

Return on investment: 13 G, 47 TKL, 4.5 SACK

Bottom line: In 2015, Marcell Dareus was suspended by the NFL for violating the league’s substance-abuse policy, and he came up for a contract extension the next season.

Teams have the option of putting clauses into contracts that would void the guaranteed money if a player gets suspended, but they elected not to do that with Dareus’ deal, and it cost them.

He was suspended, again, just months after signing the deal, but the Bills were still on the hook for the guaranteed money.

25. Drew Bledsoe

Tom Brady changed the Patriots’ plans with Drew Bledsoe. Elise Amendola / AP Photo

Sport: Football (NFL)

Year: 2001

Contract: 10 years, $103 million ($30 million guaranteed)

Team: New England Patriots

Return on investment: 2 G, 2 TD, 2 INT, 60.6 CMP%, 75.3 RAT

Bottom line: This was the largest contract in NFL history at the time, and all of the headlines said that this deal would virtually guarantee Drew Bledsoe would finish his career in New England.

Twelve months later, he was traded to Buffalo. That’s the business of the NFL. Bledsoe, the Patriots and no one besides Tom Brady could foresee Tom Brady becoming Tom Brady.

24. Eddy Curry

Eddy Curry, left, was not worth $60 million for the Knicks. Julie Jacobson / AP Photo

Sport: Basketball (NBA)

Year: 2005

Contract: 6 years, $60 million

Team: New York Knicks

Return on investment: 222 G, 15.2 PPG, 5.8 RPG, 0.6 BPG

Bottom line: In early 2005, Eddy Curry was with the Bulls and was sidelined with an irregular heartbeat. The Bulls wanted him to undergo a DNA test to see if he had a congenital heart condition, but Curry refused. However, the Knicks had no such worries about Curry’s heart, so they executed a sign-and-trade to nab Curry.

Either due to his heart issue — or due to a lack of worth ethic — Curry struggled to stay healthy and in shape while in New York. He played in just 45 percent of the possible NBA games over the length of his six-year deal.

23. Michael Jordan

Michael Jordan was underpaid in his early years. John Swart / AP Photo

Sport: Basketball (NBA)

Year: 1988

Contract: 8 years, $25 million

Team: Chicago Bulls

Return on investment: 502 Games, 31.6 PPG, 3 MVPs, 4 NBA titles

Bottom line: We reserved No. 23 for No. 23, and this entry is an outlier of sorts. Obviously, the Bulls got a great ROI so what makes this one of the worst contracts ever is from the athlete’s standpoint.

An annual salary of $2 million-$3 million was the going rate back in 1988 but eight-year deals were not. Thus, by the end of it — which coincided with the 1995-96 season in which Chicago won a record 72 games — Jordan was vastly underpaid compared to his peers such as Patrick Ewing, who made five times as much as MJ that year.

22. Billy Gillispie

Billy Gillispie went 40-27 as Kentucky’s head coach. John Russell / AP Photo

Sport: Basketball)

Year: 2007

Contract: 7 years, $17.7 million

Team: Kentucky Wildcats

Return on investment: 67 G, 40-27 record (.597 W-L%)

Bottom line: Billy Gillispie technically shouldn’t be on this list because he spent his entire two seasons as Kentucky’s head coach without a contract.

He worked on a memorandum of understanding and didn’t have an agent, and those facts would later hurt him during a settlement. Gillispie was fired after two seasons and the MOU stated that he would be due $6 million as a buyout. But since the “contract” was never signed, Kentucky didn’t legally owe him that amount.

He eventually sued Kentucky, which then countersued the very next day. In the end, the two sides settled with Gillispie receiving $2.98 million instead of the $6 million he was seeking.

21. Mike Glennon

Mike Glennon got a lot of money from the Bears for little production. Paul Sancya / AP Photo

Sport: Football (NFL)

Year: 2017

Contract: 3 years, $45 million ($18.5 million guaranteed)

Team: Chicago Bears

Return on investment: 4 G, 4 TD, 5 INT, 66.4 CMP%, 76.9 RAT

Bottom line: The $18.5 million Mike Glennon received came from four different buckets. He received $8 million in salary for the 2017 season and also a $3 million signing bonus. That accounts for $11 million.

The other $7.5 million came from two different roster bonuses — one in 2017 ($5 million) and one in 2018 ($2.5 million) that he got even though he didn’t play for the Bears in 2018.

20. Michael Johnson

Michael Johnson lasted one season in Tampa Bay. Chris O’Meara / AP Photo

Sport: Football (NFL)

Year: 2014

Contract: 5 years, $43.8 million ($24 million guaranteed)

Team: Tampa Bay Buccaneers

Return on investment: 14 G, 27 TKL, 4.0 SACK, 2 FF

Bottom line: From 2009 to 2013, Michael Johnson played for the Cincinnati Bengals, and then in 2014, he joined the Bucs. However, Johnson remained part of a group text with all Bengals players while in Tampa.

There was likely lots of shooting the breeze in the text, but there was likely also some football-related stuff, which makes it odd that a player on a different team would be allowed to be a part of it.

Johnson lasted just one disappointing season in Tampa and guess what team he joined after being cut? Cincinnati.

19. Dennis Rodman

Dennis Rodman was very popular in the late 1990s. Paula Illingworth / AP Photo

Sport: Wrestling

Year: 1999

Contract: 1 year, $1.1 million

Promotion: WCW

Return on investment: 1 match

Bottom line: During the late 1990s, Dennis Rodman wandered into the world of pro wrestling. He was certainly enough of a character to be successful, but he had no experience.

However, his name carried value with it so WCW paid him over $1 million for one single match in 1999. The match was poorly received, and 18 months later, the company went out of business with money being a main factor.

18. Diana Taurasi

Diana Taurasi got paid to not work. Ross D. Franklin / AP Photo

Sport: Basketball

Year: 2015

Contract: 1 year, $107,000

Team: UMMC Ekaterinburg

Return on investment: Did not play

Bottom line: After winning a WNBA championship in 2014, Diana Taurasi sat out the entire 2015 WNBA season and got paid to do so. Huh? Taurasi spent her summers playing in the WNBA but her winters playing overseas where the salaries were much higher. She made $107,000 per year with the Phoenix Mercury but made $1.5 million annually for her European team, UMMC Ekaterinburg.

So they decided it would be better for them if Taurasi skipped her WNBA season and UMMC did that by paying her what she would have made with the Phoenix Mercury to instead sit on the sideline.

It was a great deal for UMMC Ekaterinburg as they kept their star player healthy, and it was great for Taurasi who got paid to not work. But it was horrible for the WNBA as it highlighted the pay disparity the league had at the time.

No one expected their salaries to compete with those of the NBA, but Taurasi was getting paid 15 times as much to play in Europe than for her domestic sports league.

17. Matt Millen

Matt Millen, right, was a much better player than NFL executive. Duane Burleson / AP Photo

Sport: Football (NFL)

Year: 2001

Contract: 5 years, $25 million

Team: Detroit Lions

Return on investment: 80 G, 21-59 record (.263 W-L%)

Bottom line: Despite having no front-office experience, Matt Millen was hired as the Lions’ president, CEO and general manager.

Before the hiring, he even told the team’s owner that he wasn’t qualified to which owner William Clay Ford Sr. — whose grandfather founded Ford Motor Company — said, “You’re smart. You’ll figure it out.”

Millen may have been smart, but he didn’t figure it out. Fans were so upset at his job performance that chants of “Fire Millen” broke out during games for the Pistons, Red Wings, Michigan State and even at WrestleMania 23, which took place in Detroit.

16. Antonio Bryant

Antonio Bryant played zero games for the Bengals. Al Behrman / AP Photo

Sport: Football (NFL)

Year: 2010

Contract: 4 years, $28 million ($8 million guaranteed)

Team: Cincinnati Bengals

Return on investment: 0 games

Bottom line: Only in pro sports could you make $8 million for five months of work and not even work during that time.

Antonio Bryant signed with the Bengals in May 2010 after having knee surgery. He was barely able to practice while recovering, and the only time he put his jersey on was for picture day.

By August, the Bengals realized they made a mistake and cut him without Bryant playing a single snap.

15. Gilbert Arenas

File the Gilbert Arenas-Wizards deal under “When Things Don’t Go According to Plan.” Mark Duncan / AP Photo

Sport: Basketball (NBA)

Year: 2008

Contract: 6 years, $111 million

Team: Washington Wizards

Return on investment: 55 G, 20.2 PPG, 3.9 RPG, 6.7 APG

Bottom line: It would be one thing if Gilbert Arenas was just bad on the court, but he was even worse off it and specifically in the team’s locker room. He and a teammate had an unsettled debt over a card game, so they drew guns on each other in the locker room like a scene from the wild, wild West.

Arenas then compounded that by making a joke out of the situation with an infamous photo, and the NBA suspended him shortly thereafter. He was sentenced to two years of probation and traded to Orlando as Washington tried to cleanse itself of Arenas and his contract.

14. Albert Pujols

Memo to MLB teams: Don’t give 10-year deals to 32-year-old players. Chris Carlson / AP Photo

Sport: Baseball (MLB)

Year: 2012

Contract: 10 years, $240 million

Team: Los Angeles Angels

Return on investment: 1,118 G, .258 AVG, 211 HR, 746 RBI

Bottom line: The Angels, Cardinals and Marlins all offered Pujols 10-year deals in 2012. They all were paying for past performance instead of future results. Pujols rejected returning to the Cardinals because they offered only $210 million and he turned down the Marlins because they wouldn’t include a no-trade clause.

Thus, the Angels won the Pujols sweepstakes, and once the playing part of the deal ends, the Angels will owe Pujols another $10 million as a part of a 10-year personal services contract.

13. Tom King

Tom King played his college basketball at Michigan. Wikimedia Commons

Sport: Basketball (NBA)

Year: 1946

Contract: 1 year, $16,500

Team: Detroit Falcons

Return on investment: 58 G, 5.1 PPG, 0.6 APG, 23.7 FG%

Bottom line: The NBA’s first year was in 1946, and Tom King, who played at Michigan, signed with the nearby Detroit Falcons.

Back then, players often had second jobs, and King’s second job was to serve as the Falcons’ business manager/public relations director. Because of all of his roles for the team, King negotiated a salary for himself that made him the highest player in the league despite paltry on-court production.

In a surely related note, just weeks after the Falcons’ season ended, they folded due to huge financial losses.

12. Rafa Marquez

Rafa Marquez admitted he made a mistake playing in the MLS. Bill Kostroun / AP Photo

Sport: Soccer (MLS)

Year: 2010

Contract: 4 years, $20.4 million

Team: New York Red Bulls

Return on investment: 50 GM, 1 G, 7 A

Bottom line: The MLS has a rule called the designated player rule, which allows teams to sign players and have their salary circumvent the salary cap.

It’s reserved for special players such as David Beckham, and Rafa Marquez was seen in that same vein as Becks. But while Marquez’s salary was in line with Beckham’s, his temperament, level of play and attitude certainly were not.

He was indifferent during his time in New York and admitted afterward that he made a mistake in signing with the MLS.

11. Joe Louis

Joe Louis, left, won 45 fights in his career. AP Photo

Sport: Boxing

Year: 1935

Contract: 10 years

Team: N/A

Return on investment: 45-1 record (31 KO), won heavyweight championship

Bottom line: At 20 years old, Joe Louis signed two contracts — one with his manager and one with his promoter — that went into effect when he turned 21 in 1935.

Among the stipulations were that 25 percent of Louis’ boxing earnings would go to both individuals, meaning that Louis would only get half of his purse. Also, among the conditions of the contract were that the Black Louis couldn’t have his picture taken with a white woman nor could he gloat over an opponent.

In part due to this contract, Louis spent the later years of his life in debt, and when his mother passed away, the IRS seized $667 she had willed to her son.

10. Yoenis Cespedes

Yoenis Cespedes lost money because he got hurt being chased by a wild boar. David Zalubowski / AP Photo

Sport: Baseball (MLB)

Year: 2017

Contract: 4 years, $110 million

Team: New York Mets

Return on investment: 119 G, .282 AVG, 26 HR, 71 RBI

Bottom line: After a non-baseball injury in 2019 cost Yoenis Cespedes the entire season, his’ contract had $23.5 million cut from it and converted into an unlikely-to-reach bonus.

As for that injury, it came when Cespedes suffered multiple ankle fractures on an accident at his Florida ranch. He reportedly was being chased by a wild boar and stepped in a hole while getting out of the way which caused the injury. Seriously.

Cespedes’ contract prohibits certain activities that increase the risk of injury, and because of that, the Mets were able to recoup some of the money from the contract.

9. Allan Houston

Allan Houston’s contract was so bad it forced an NBA rule change. Frank Franklin II / AP Photo

Sport: Basketball (NBA)

Year: 2001

Contract: 6 years, $100.4 million

Team: New York Knicks

Return on investment: 307 G, 19.6 PPG, 3.0 RPG, 2.4 APG

Bottom line: Allan Houston’s contract was so disastrous that the NBA created a new clause in their collective bargaining agreement to prevent other teams from making the same mistake.

The “Allan Houston Rule” was created in 2005, which was essentially an amnesty clause. It allowed teams to waive a player without his contract counting against the NBA’s luxury tax.

The player still received whatever money that was owed to him, but those financials didn’t figure into the franchise’s tax threshold.

8. Albert Haynesworth

Albert Haynesworth got way overpaid. Evan Vucci / AP Photo

Sport: Football (NFL)

Year: 2009

Contract: 7 years, $115 million ($41 million guaranteed)

Team: Washington Football Team (formerly Redskins)

Return on investment: 20 G, 53 TKL, 6.5 SACK, 0 FF

Bottom line: Here’s what a Redskins teammate said of Albert Haynesworth in 2013: “His goal was to come here, make a large signing bonus and then get released and not have to do any of the work.”

That pretty much sums up Haynesworth’s time in Washington, D.C., as he came in out of shape, feuded with teammates and called out the coaching staff.

He was the NFL’s first $100 million defensive player, and it would be years before there was another because of the bad taste Haynesworth’s deal left in everyone’s mouths.

7. Charlie Weis

Charlie Weis, right, won 26 games as Notre Dame coach. Michael Conroy / AP Photo

Sport: Football (NCAA)

Year: 2006

Contract: 10 years, $36 million

Team: Notre Dame

Return on investment: 50 G, 26-24 record (.520 W-L%)

Bottom line: After joining Notre Dame in 2005, Charlie Weis coached just seven games before earning a new contract courtesy of a 10-year extension.

That’s a decision the Fighting Irish would later regret as the team fired him in 2009 but still owed him six years on the deal.

To settle, Notre Dame had to agree to a buyout of nearly $19 million, which was paid over six years.

6. Chris Davis

Chris Davis, right, has struck out over 1,800 times in his MLB career. Eric Risberg / AP Photo

Sport: Baseball (MLB)

Year: 2016

Contract: 7 years, $161 million

Team: Baltimore Orioles

Return on investment: 518 G, .198 AVG, 92 HR, 230 RBI

Bottom line: If you were bad at your job — and you knew it — but were signed to a guaranteed contract with your employer, would you voluntarily quit?

That’s a dilemma that Davis confronted after the 2019 season but he elected to not retire because, in his words, he still has something left in the tank.

He may have meant something left in the bank because there is no chance in hell he was going to walk away from $69 million over the next three years.

5. Ricky Williams

Ricky Williams missed out on a big payday with the Saints. Stephen J. Carrera / AP Photo

Sport: Football (NFL)

Year: 1999

Contract: 8 years, $68.4 million ($8.8 million guaranteed)

Team: New Orleans Saints

Return on investment: 38 G, 3,129 YDS, 16 TD, 3.8 AVG

Bottom line: This was a great deal for the Saints but a horrible one for Williams.

With rapper Master P serving as his agent, Williams negotiated a deal that was extremely incentive-heavy and included many unlikely-to-reach bonuses such as $3 million if Williams broke the all-time single-season rushing record.

All in all, Williams ended up with just over $12 million from the contract, thus leaving over $55 million on the table.

4. JaMarcus Russell

JaMarcus Russell is one of the biggest busts in NFL history. Jack Dempsey / AP Photo

Sport: Football (NFL)

Year: 2007

Contract: 6 years, $61 million ($31.5 million guaranteed)

Team: Oakland Raiders

Return on investment: 31 G, 18 TD, 23 INT, 52.1 CMP%, 65.2 RAT

Bottom line: Credit goes to JaMarcus Russell’s agents for negotiating a front-heavy contract which protected the quarterback in the event that he was a bust.

Well, he was a bust, but because of the deal, Russell made over $36 million, which was a 65 percent raise over the player in the same draft slot one year earlier.

Russell’s team and the Raiders went back and forth for months to finalize the deal, and ESPN reported that the contract had seven different drafts before completion.

3. Michael Vick

What could have been with Michael Vick. John Bazemore / AP Photo

Sport: Football (NFL)

Year: 2005

Contract: 10 years, $130 million ($37 million guaranteed)

Team: Atlanta Falcons

Return on investment: 31 G, 35 TD, 26 INT, 53.9 CMP%, 74.4 RAT

Bottom line: Two years into this deal, Michael Vick was convicted of dogfighting and sentenced to 23 months in prison. But there were also financial implications, and the Falcons argued that Vick should have to return part of his signing bonus since he used the money to fund the elaborate dogfighting scheme.

An arbitrator agreed with the Falcons’ assessment, and Vick was forced to repay $19.97 million of his signing bonus. As a result, Vick ended up making just $7.59 million from a contract that was worth up to $130 million.

2. Joe Smith

The Timberwolves lost more than money with Joe Smith. Mark J. Terrill / AP Photo

Sport: Basketball

Year: 1999

Contract: 2 years, $3.8 million

Team: Minnesota Timberwolves

Return on investment: 121 G, 11.3 PPG, 6.9 RPG, 1.3 APG, 1.2 BPG

Bottom line: In 1999, the Timberwolves attempted to circumvent the salary cap by signing Joe Smith to three successive one-year contracts below market value.

In order for Smith to accommodate their wishes, the team then promised they would give him a $68 million deal after the three one-year contracts. The NBA caught wind of the plan before the third year of the pact and voided Smith’s contract, fined the team $3.5 million, suspended both the owner and GM and stripped the team of four first-round draft picks!

Moral of the story: Cheaters never win.

1. Bobby Bonilla

The Mets will be paying Bobby Bonilla until 2035. BarDown / Twitter

Sport: Baseball

Year: 2000

Contract: 1 year, $5.9 million

Team: New York Mets

Return on investment: Did not play for Mets

Bottom line: The above contract was what the Mets owed Bonilla when they cut him. But instead of simply paying that amount, they decided to take an offer from Bonilla’s manager on deferred payments with an 8 percent annual rate. The deferred payments didn’t kick in until 2011 and would run for… 25 years.

So every July 1 from 2011 through 2035, Bonilla receives a payment of $1.19 million, which nets him a total of $29,831,205. Bonilla last played for the Mets in 1999 and last played in the majors in 2001, but he’ll keep getting checks until he’s 72 years old.

Why did the Mets decide to enter this agreement? Their owner Fred Wilpon was invested in a Ponzi scheme with Bernie Madoff and thought his ROI with Madoff outweighed the interest rate of the deferred deal. Oops.