The 9 Biggest Contracts In The History Of Sports

Most professional athletes do pretty well for themselves, but the best players in various sports have the potential to retire with generational wealth based on the absurd amount of money certain teams are willing to fork over to secure their services.

At this point, it feels like pro athletes are resetting the market on an annual basis based on the increasingly massive contracts that have been handed out over the past few years.

You won’t be shocked to learn the richest deals in sports history have all been handed all fairly recently, but you may be shocked by the size of the bags that were secured by the people who received them.

1. Juan Soto: $765 Million

The fact that there’s no hard salary cap in Major League Baseball means plenty of teams won’t think twice about breaking the bank for a superstar, and the Mets did exactly that when they gave Juan Soto the biggest contract in history after he entered free agency following what turned out to be his only season with the Yankees.

It’s a bit hard to imagine the 26-year-old Dominican phenom will end up playing for the entirety of the 15-year deal he signed at the end of 2024 (which also included a $24 million signing bonus), but if he does, he’ll end up getting paid close to $315K for every regular season game he suits up for.

2. Shohei Ohtani: $700 Million

There was zero doubt there was going to be a massive bidding war when Shohei Ohtani became a free agent after wrapping up his final season with the Angels, and he had a number of suitors before the Dodgers prevailed with a 10-year contract worth $700 million.

It’s pretty easy to understand why Los Angeles went that route when you consider Ohtani is a generational player who has already helped them win a World Series, and while his deal is smaller than Soto’s, the fact that it’s also shorter means he’s getting paid over $430,000 whenever he steps onto the field.

3. Lionel Messi: $674 Million

Lionel Messi is one of the greatest soccer players of all time, and while he may have been a little bit past his prime when he re-upped his contract with Barcelona in 2017, the club was still more than willing to give him a four-year extension worth $674,000,000.

That was the largest deal in sports history at the time it was signed and remains the biggest one a soccer player has ever received as far as the total amount of money is concerned—although his longtime rival arguably got a better contract a couple of years after that one expired.

4. Cristiano Ronaldo: $536 Million

As you can likely guess, the rival in question is Cristiano Ronaldo, who headed from England to Saudi Arabia after being targeted in the push that brought a number of notable soccer players to the Saudi Pro League with the help of the virtually endless amount of oil money at its disposal.

Al-Nassr lured Ronaldo to the Middle East with a contract that paid him around $536 million for two-and-a-half years of work, which was the richest annual contract in soccer history at the time when you consider he was making close to $215 million every 365 days (we’ll get to the man who ended up surpassing him in a moment).

5. Patrick Mahomes: $450 Million

Patrick Mahomes is the only NFL player on this list, and the Chiefs QB turned plenty of heads when he signed what was then the biggest contract ever given to a professional athlete in 2020 when Kansas City revealed it was going to pay him $450 million over the course of ten years with an extension set to expire after the 2031 season.

Not all of that money is guaranteed, but it’s worked out pretty well for both parties involved so far when you consider the Chiefs have made the Super Bowl four times since he signed the deal and will have the chance to win their third championship in the row against the Eagles.

6. Karim Benzema: $447.3 Million

Al-Nassr put the Saudi Pro League on notice when it signed Ronaldo, but it didn’t take very long for Al-Ittihad to respond by making a splash of its own by landing Karim Benzema.

In 2023, the club signed the former Real Madrid striker to a two-year deal worth $447,302,608, and there isn’t a single professional athlete who’s earned a higher annual salary than the man who’s currently raking in over $223 million a year.

7. Mike Trout: $426.5 Million

Shohei Ohtani spent six seasons playing alongside the man who signed what was both the biggest contract in MLB history and second-biggest ever behind Messi when the Angels inked Trout to a 12-year, $426.5 million contract deal prior to the 2019 season where he won his third AL MVP award.

Unfortunately, the Angels have largely declined to invest in additional talent to support Trout (who is their only big name in the wake of Ohtani’s departure), and while the future doesn’t look too bright for a team that hasn’t made the playoffs in a decade, it’s probably easier to deal with that kind of mediocrity when you’re making around $220K per game.

8. Canelo Álvarez: $365 Million

This is one of the more unconventional entries on this list when you consider most boxers don’t sign multi-year contracts, but Canelo Álvarez did exactly that when he agreed to a deal with DAZN, the streaming service that earned the right to air his next 11 fights when it forked over $365 million for that privilege in 2018.

9. Mookie Betts

Mookie Betts also received a cool $365 million from the Dodgers, who really kicked off the spending spree they’ve been on in recent years with the 12-year contract he received in 2021.

Betts also played an instrumental role in the World Series they won the season before he got a new deal and was also a key contributor in the championship the team took home during Ohtani’s first campaign.

As a result, all signs point to those investments paying off based on how things have been trending.