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10 biggest contracts in MLB history

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In recent years, there has been a lot of competition for the biggest MLB contract ever.

Spending in baseball appears to be out of control, at least among some of the richest MLB owners who have no problem giving out massive contracts. Therefore, some of the biggest contracts in MLB history have come in the last handful of years. But what is the biggest MLB contract ever?

Counting down to the biggest MLB contract ever

To show you just how far baseball has come financially, we wanted to show you some of the largest MLB contracts of all time.

Oddly enough, some of the biggest free agency deals of the 2023 offseason didn’t even make the cut. Nevertheless, spending has sky-rocketed over the last decade or so, helping to produce this list of the 10 biggest contracts in MLB history.

10. Gerrit Cole – 9 Years, $324 Million

Gerrit Cole is the only pitcher who has made it onto our list of the 10 largest MLB contracts. When the Yankees were desperate for an ace after the 2019 season, they gave Cole a nine-year, $324 million deal to secure his services.


Cole was on the heels of a dominant 2019 season in which he led the American League in both ERA and strikeouts. Oddly enough, Cole has never won a Cy Young and isn’t always the obvious choice for the best pitcher in baseball. Nevertheless, no pitcher has been able to secure a contract worth more than his $324 million deal.

9. Giancarlo Stanton – 13 Years, $325 Million

At the time that Giancarlo Stanton signed his 13-year, $325 million contract with the Marlins, it was the biggest the sports world had ever seen. Back then, Stanton was the most feared power hitter in the game.

Oddly enough, everything that has happened since then has been a little predictable. The small-market Marlins couldn’t afford to keep paying Stanton so much, so they unloaded him and most of his contract on the Yankees. His performance with the Yankees hasn’t exactly matched his salary, as Stanton is now a DH who hits an occasional homer but doesn’t do much else, making this contract a good example of the risk involved in these types of contracts.

8. Corey Seager – 10 Years, $325 Million

It’s funny how desperation and large contracts often go hand-in-hand. The Rangers were desperate to revamp their lineup, so they made Corey Seager a $325 million promise. At the time, Seager was just one year removed from being a World Series MVP, so the Rangers thought Seager was worth the investment.

It’s still too soon to know for sure if it was worth it, although Seager didn’t exactly live up to the contract during his first year in Texas. 


7. Bryce Harper – 13 Years, $330 Million

In a way, it’s surprising to see Bryce Harper so far down this list. When he signed with the Phillies for 13 years and $330 million in 2019, it was the largest contract in MLB history.

But just a few years later, it’s not even in the top five.

On the other hand, at 13 years, Harper’s contract is still one of the longest contracts signed, especially for a player who had already played seven seasons in the majors. Plus, $330 million over 13 years isn’t exactly chump change, and after leading the Phillies to the World Series in 2022, Harper is on his way to earning his massive contract. 

6. Fernando Tatis Jr. – 14 Years, $340 Million

The Padres certainly took a risk when they signed Fernando Tatis to a contract extension worth $340 million over 14 years. Tatis was just 22 years old at the time, although he had already won a Silver Slugger award and went on to lead the National League in home runs in 2021.

On the downside, Tatis didn’t play at all in 2022 and was suspended at the start of the 2023 season. Therefore, San Diego has already experienced the highs and lows of a contract of this size.

Of course, Tatis is still young and could still live up to this massive contract. However, it goes without saying that no other player on this list had so little experience in the majors when he signed this deal.

5. Francisco Lindor – 10 Years, $341 Million

The Mets gave up some substantial pieces in a trade with Cleveland to get Francisco Lindor, so after that, they had to pay him.

At the time, Lindor already had multiple Gold Gloves and multiple Silver Slugger awards, making it clear that he is one of the best two-way players in the game. This contract also means that Lindor will be in New York through the 2031 season when he’ll be 37, which means that if Lindor doesn’t age well, neither will this contract.

4. Manny Machado – 11 Years, $350 Million

Manny Machado nearly made it onto this list twice because he’s signed two different contracts worth $300 million. In 2019, he signed a 10-year deal worth $300 million. But that deal wasn’t enough, so when Machado indicated that he would opt out of the deal after the 2023 season, the Padres quickly signed him to a new 11-year, $350 million contract.

That contract comes with a full no-trade clause, keeping Machado in San Diego through the 2033 season. While that seems like a long contract, Machado was only 30 at the time of the $350 million extension and has a chance to live up to that deal.

3. Aaron Judge – 9 Years, $360 Million

Coming off his historic 2022 season, the Yankees had no choice but to give Aaron Judge one of the biggest contacts in MLB history.

He’s clearly worthy of that kind of contract and has been an integral part of the Yankees throughout his career. According to reports, the Giants offered Judge a contract worth over $400 million, which could have potentially been the largest contract in MLB history. But in the end, Judge stayed in New York and should be satisfied with his $360 million contract.

2. Mookie Betts – 12 Years, $365 Million

The Red Sox weren’t willing to give Mookie Betts one of the largest MLB contracts of all time, but the Dodgers did. Soon after the 2020 blockbuster deal that sent Betts to Los Angeles, the Dodgers gave him a 12-year, $365 million extension, keeping him in Los Angeles through the 2032 season.

While Betts still has a lot of years left on that deal, he’s continued to be an all-star and one of the best players in baseball. In fact, he won both a Gold Glove and Silver Slugger in 2022, so there’s no doubt that he’s still an elite player. The only thing left is for Betts to help the Dodgers win a World Series.

1. Mike Trout – 12 Years, $426.5 Million

One day soon, Mike Trout’s teammate with the Angels Shohei Ohtani is likely to pass him for the biggest MLB contract ever. But for the time being, Trout still has that honor, and fittingly so.

The 12-year, $426 million extension he got with the Angels came after years of being the best player in the game and someone who will one day be considered among the greatest of all time.

Whether his recent injury issues allow him to fully live up to that deal remains to be seen. But Trout was still worth the risk of such a huge contract. In fact, Trout was the highest-paid player in North American sports history until Patrick Mahomes came along.

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