The Largest Contracts In Professional Sports History

By on April 6, 2019 in ArticlesSports News

When Mike Trout inked a 12-year, $430 million deal to stay with the Los Angeles Angels, he immediately made history. That amount is – by far– the largest guaranteed sum that a professional athlete has ever received. Trout's average salary will be close to $36 million.

It's a big responsibility: if you really want to overdramatize things, Trout has essentially been tasked with saving baseball. The Angels will look to return to prominence with him, and his re-signing is a major move in a summer where star free agents have seen their contract negotiations drag out.

While Trout is now officially the highest-paid athlete in the world, he's hardly the only one making a ton of money. Let's take a look at the ten biggest contracts in professional sports history. Note that these deals have to be officially cited, so soccer stars like Lionel Messi won't make the cut, since their official contract deals have never been confirmed. We're also only looking at contracts that were guaranteed – this doesn't take into account any performance or promotional bonuses.

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Mike Trout, Los Angeles Angels – 12 years, $430 million

Since becoming a full-time major leaguer in 2012, Trout has made seven All-Star teams and won two AL MVP awards. However, it hasn't translated to much team success. The Angels have made the playoffs just once in that span, getting swept during the 2014 postseason. Trout will have to lead the Angels on multiple deep playoff runs to truly make this a worthwhile deal. It's probably not fair to put so much weight on one player's shoulders, but then again, no one's ever made this much money before.

Canelo Alvarez, DAZN – 5 years, $365 million

Trout may hold the record for most overall money, but Alvarez blows him out of the water when it comes to annual salary. The boxer signed a five-year, 11-fight deal last October with the streaming service DAZN. The contract will pay him a whopping $73 million per year, with each fight being worth about $33.18 million.

Bryce Harper, Philadelphia Phillies – 13 years, $330 million

After Harper signed his deal, it was only a matter of time before his buddy Trout got a major extension, too. Harper's free agency saga dragged out for nearly the entire offseason; he signed just about a month before Opening Day. Eventually, he left Washington to join an NL East rival. The Phillies made back-to-back World Series appearances in 2008 and 2009, but haven't had a winning record since 2011. Harper is expected to immediately help turn the team's fortunes around.

Giancarlo Stanton, Miami Marlins – 13 years, $325 million

This is the largest contract on this list that wasn't signed within the past year. Stanton re-signed with the Marlins on this massive deal but was dealt to the Yankees just two seasons later. That means the Bronx Bombers are picking up the majority of the tab on Stanton. However, if Stanton doesn't opt out of his contract after the 2020 season, the Yankees will receive $30 million in salary cap relief from the Marlins.

Manny Machado, San Diego Padres – 10 years, $300 million

Remember when Machado had the biggest deal of the 2019 MLB offseason? Seems like so long ago. The Padres have struggled mightily in relative anonymity for the past decade, so signing a star like Machado is a huge deal. There's a catch, though: Machado can opt out after five seasons. If he doesn't like the state of the team at that point, the Padres will lose him for nothing.

Alex Rodriguez, New York Yankees – 10 years, $275 million

A-Rod opted out of his existing deal in 2007 to sign a 10-year, $275 million extension with the New York Yankees. The end of Rodriguez's career was marred by injury and scandal. And throughout his stay, he was a polarizing figure in New York, especially playing next to hometown hero Derek Jeter. But Rodriguez did collect his only World Series ring during this contract, helping the Yankees beat the Phillies in 2009. It's the franchise's last World Series victory.

Nolan Arenado, Colorado Rockies – 8 years, $260 million

Arenado is no stranger to the long ball, having hit at least 37 home runs the past four seasons. While critics may say it's because he plays half of his games at Coors Field, the Rockies were still smart to lock him up. In addition to four All-Star appearances, Arenado is a defensive wizard. He's won a Gold Glove every season he's been in the league.

Alex Rodriguez, Texas Rangers – 10 years, $252 million

Rodriguez is the only player to appear twice on this list. This deal in 2000 set the bar for massive MLB contracts. He ultimately only spent three years with the Rangers, winning the AL MVP award in 2003 but failing to make the playoffs during his tenure with the team. The Rangers traded Rodriguez to the Yankees before the 2004 season. Four years later, he signed a new (at the time) record-setting deal to stay in New York.  

Miguel Cabrera, Detroit Tigers – 8 years, $247 million

Cabrera's contract is a bit different than some of the others on this list in that it kicked in after he was past his prime. In 2014, the Tigers offered their star first baseman an eight-year extension starting in 2016. Cabrera was 33 when the deal began, and he'll be in his forties when it ends. Injury is also a risk – Cabrera spent most of 2017 playing with two herniated discs in his back, and played just 38 games last season due to hamstring and biceps injuries.

Albert Pujols, Los Angeles Angels – 10 years, $240 million

In 11 seasons with the St. Louis Cardinals, Pujols made nine All-Star teams and won three MVP awards. He also led the league in runs scored five times, slugging and on-base percentage three times each, home runs twice, and batting average once. Since signing this deal with the Angels in 2012, Pujols has made just one All-Star team, in 2015. And the only statistical categories he's led the league in? Grounding into double plays, which he's done twice (in 2014 and 2017). Pujols also hasn't hit higher than .285 since joining the Angels. He's still a future Hall of Famer, but it'll be largely based on what he did before signing this contract.

Robinson Cano, Seattle Mariners – 10 years, $240 million

Before the 2014 season, Cano signed this deal with the Mariners. He turned down a seven-year, $175 million contract to stay with the Yankees. Cano did make three All-Star appearances in five seasons with the Mariners, but he was suspended 80 games last year for the use of performance-enhancing drugs. The Mariners traded him to the Mets this offseason. Cano promptly hit a home run in his first at-bat with his new team.

Articles Written by Joey Held
If there's a story anywhere in the world of music, sports, or entertainment, Joey wants to tell it. He's been freelancing since 2010, and prior to that, he attended the University of Miami, where he double majored in broadcast journalism and sport administration. A Chicago native, Joey currently resides in Austin, TX. Follow him on Twitter and always feel free to suggest a song for his next karaoke performance. Joey's favorite billionaire is Mark Cuban.
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