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The 20 most lucrative player contracts in sporting history

WWOS staff

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Sport's richest ever contracts
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Sport's richest ever contracts

Golf star Dustin Johnson has just signed a $175 million deal to be the marquee man for Greg Norman's Saudi-backed LIV Golf tour.

Yet that deal doesn't go close to making the top 20 richest sports contracts ever signed.

The mega-deals that belong in the truly elite bracket have been signed by a mix of the world's best footballers and stars of America's biggest sports leagues. Surprisingly, despite its limited global profile in comparison to the NFL and the NBA, baseball's MLS has the most representatives on the mega-contract list.

Here are the 20 largest ever contracts handed out in sporting history.

Attribution: Getty
20. Anthony Rendon (baseball) - seven years, $342M
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20. Anthony Rendon (baseball) - seven years, $342M

At the end of the 2019 season, both Anthony Rendon and Washington Nationals teammate Stephen Strasburg entered free agency.

Nationals owner Mark Lerner said the team could not afford both stars, and chose Strasburg, leaving Rendon to sign an almost identical deal with the Los Angeles Angels.

Attribution: Getty
19. Stephen Strasburg (baseball) - seven years, $342M
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19. Stephen Strasburg (baseball) - seven years, $342M

One of the most-hyped pitching prospects in history, Strasburg hit the ground running with the Washington Nationals in 2010 and carved out a very impressive first decade in Major League Baseball, culminating in a World Series MVP award in 2019.

Just a couple of months after that success he was rewarded with the biggest-ever contract for a pitcher, and a seven-year extension with the Nationals.

Attribution: Getty
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18. Miguel Cabrera (baseball) - eight years, $345M
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18. Miguel Cabrera (baseball) - eight years, $345M

Miguel Cabrera's eight-year deal with the Detroit Tigers handed out in 2016 made him a record-holder in all of Detroit sports, with the $248 million USD amount the largest handed out to an athlete in the Motor City.

Unfortunately for the Tigers, the veteran's body broke down almost immediately after signing on the dotted line and he's not added to his 11 All-Star appearances since 2016.

Attribution: Getty
17. Alex Rodriguez (baseball) - 10 years, $351M
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17. Alex Rodriguez (baseball) - 10 years, $351M

You've got to wonder just what kinds of figures Alex Rodriguez could've earned if he played now, given this monster extension with the Yankees was signed in 2008.

Rodriguez won a World Series title the following season, but the deal didn't come without controversy either.

He was suspended for the entire 2014 season after his involvement in a doping scandal.

Attribution: Getty
16. Josh Allen (NFL) - six years, $359M
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16. Josh Allen (NFL) - six years, $359M

Josh Allen became one of the highest-paid players in NFL history when he signed an extension with the Buffalo Bills in 2022.

Of Allen's $258 million USD deal, $150 million is guaranteed. The guaranteed money is the most in a single contract in NFL history, surpassing Patrick Mahomes' $141.5 (USD) million guaranteed.

Attribution: Getty
15. Nolan Arenado (baseball) - eight years, $362M
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15. Nolan Arenado (baseball) - eight years, $362M

Nolan Arenado looked set to remain a member of the Colorado Rockies for the majority of his career when he signed an eight-year deal in 2019, but it all went south.

Just a year later, he requested a trade citing "disrespect" from people within the organisation.

He was eventually traded to the St Louis Cardinals in February 2021 along with $51 million USD in exchange for five players.

Attribution: Getty
14. Max Verstappen (F1) - five years, $383M
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14. Max Verstappen (F1) - five years, $383M

After claiming his first Formula 1 world championship in 2021, Max Verstappen recommitted to Red Bull Racing on a monster new deal.

The 24-year-old is signed through until the 2028 season in a massive statement of intent from Red Bull as well as a show of commitment from Verstappen himself.

Attribution: Getty
13. Manny Machado (baseball) - 10 years, $418M
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13. Manny Machado (baseball) - 10 years, $418M

Manny Machado was already a four-time All-Star and two-time Golden Glove Award winner when he signed what was then the biggest free-agent contract in American sports history in 2019.

The decade-long deal includes an opt-out clause after the fifth season and also includes a limited no-trade clause.

Attribution: Getty
12. Gerrit Cole (baseball) - nine years, $451M
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12. Gerrit Cole (baseball) - nine years, $451M

Gerrit Cole was a major winner after hitting the free agency market when he signed a world-record deal for a pitcher with the New York Yankees.

He became the first pitcher in MLB history to earn over $300 million USD, and has the option of opting out of the nine-year deal after the fifth year.

Attribution: Getty

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