The Biggest Contracts in MLB History

MLB's offseason calendar is in full swing. The general manager meetings are in the books, and we're now less than a month from the winter meetings. Those festivities will begin Dec. 3 in Nashville, Tennessee. Not a lot of free agent movement has happened just yet, but we have a chance very soon to see Shohei Ohtani sign the biggest MLB contract ever.

Rumor has it the two-way superstar would like to sign quickly, and could do so before the winter meetings begin. We know the dude is going to get paid handsomely. The real question is: How high will the number be? MLB Trade Rumors is predicting a 12-year, $528 million contract for baseball's best player.

As you can imagine, that would shatter all kinds of contract records. Before teams start opening up their checkbooks to sign players this winter, here are the 10 biggest MLB contracts in baseball history.

Biggest MLB Contracts Ever: No. 10-6

10. Gerrit Cole: Nine years, $324 million

Gerrit Cole's nine-year contract with the New York Yankees gets extra points because he's the only pitcher on this list. He's also been a pillar of consistency for the Bombers. Cole's first campaign was the pandemic-shortened 2020 season. He still made all 12 of his possible starts, and he's followed that up with three straight years of 30-plus starts.

Cole has posted a 51-23 record across 108 starts as a Yankee (664 innings). It's accompanied by a 3.08 ERA, 1.01 WHIP (walks plus hits per inning pitched), and 816 strikeouts. After a stellar 2023 season (15-4 record, 2.63 ERA and 222 strikeouts in 209 innings), he's expected to add his first Cy Young Award to these accomplishments.

8 (Tie). Giancarlo Stanton: 13 years, $325 million

Giancarlo Stanton signed this monster deal with the Miami Marlins, but just about everyone expected him to finish the contract playing somewhere other than in South Florida. Heck, Stanton probably knew this as the ink was drying.

Stanton's long-term extension started in 2015. It began with a pair of 27-homer campaigns for the Marlins while playing no more than 119 games in a single season. And then came 2017 when he took home NL MVP Award honors thanks to a 59-homer, 132-RBI performance.

That led to him getting dealt to the Yankees the following offseason. Stanton has four years of at least 24 homers for New York since 2018, and he's also performed well in the postseason. However, his inability to stay healthy and a general decline in overall production — his OPS (on-base plus slugging rating) went from .894 in 2019 to .695 in 2023 — is making his contract more of a problem than anything else.

8. (Tie) Corey Seager: 10 years, $325 million

Corey Seager's huge, long-term deal to join the Texas Rangers following the 2021 season was part of a huge spending spree. Texas also agreed to pay Marcus Semien $175 million that same winter. That gave them a very expensive — but also very productive — middle of the infield.

And, of course, this was all justified in 2023 with the Rangers winning their first World Series title. Seager was a big reason for the club's success, and it was punctuated with his second career World Series MVP Award.

Between 2015 and 2021 with the Los Angeles Dodgers, Seager never posted a 30-homer campaign and finished with 80-plus RBIs just once. He's done that in each of his first two years in Texas.

7. Bryce Harper: 13 years, $330 million

Philadelphia Phillies fans are still pumped over the fact that Bryce Harper signed a 13-year deal with the club. He was an integral part of Philly's 2022 World Series run, and he's already among the franchise's postseason home run leaders.

During his five years with the Phillies, Harper is hitting .284/.395/.536 with 122 home runs, 368 RBIs and 387 runs scored. He also took home the 2021 NL MVP Award, along with two Silver Slugger Awards while also appearing in one All-Star Game.

6. Fernando Tatis Jr.: 14 years, $340 million

A lot has changed since the San Diego Padres signed Fernando Tatis Jr. to this $340 million deal. When the ink dried, Tatis was seen as the club's starting shortstop for the foreseeable future. Some injuries and a performance-enhancing drug suspension later, he's now the Padres' right fielder.

The shift in position has gone pretty well, though. That's evidenced by his Gold Glove Award and Platinum Glove Award from 2023. Tatis has been active for two seasons since this deal has gone into effect (2021 and 2023). Between those campaigns, he's won those defensive awards, one Silver Slugger Award, and placed third in the 2021 NL MVP Award voting.

His .770 OPS from this past year is a steep drop from what he did in 2021 (.975), but it had also been more than a year since he took the field in a big-league game. He'll only be entering his age-25 season in 2024 as well.

Biggest MLB Contracts Ever: No. 5-1

5. Francisco Lindor: 10 years, $341 million

Even with a lackluster start to his New York Mets career in 2021, Francisco Lindor has already cemented himself as one of the franchise's best shortstops. Between his performances in 2022 and 2023, he holds several single-season Mets records at his position.

This includes home runs (31 in '23), RBIs (107 in '22) and fWAR (Fangraphs' wins above replacement) (6.6 in '22). In fact, he owns the two best single-season performances in each of these three categories. Lindor added to his accomplishments in 2023 by becoming the fourth Mets player to produce 30 homers and 30 steals in one year, which helped him earn his third career Silver Slugger Award.

4. Manny Machado: 11 years, $350 million

During the same offseason Harper signed with the Phillies, Manny Machado signed a 10-year, $300 million deal with the Padres. The biggest difference between these two deals was that Harper locked himself in for the duration of his contract, while Machado had an opt-out looming prior to 2024.

San Diego made that a moot point early in the 2023 season by locking in its third baseman for another 11 years and $350 million.

Machado has been with the Padres since 2019. He's finished within the top 20 of NL MVP voting three times, and that includes two different top-three finishes. The sweet-swinging right-handed hitter has also produced three seasons of 30-plus homers. His 138 homers as a member of the Padres already have him within the top 5 in franchise history and in striking distance of the top spot once 2024 rolls around.

3. Aaron Judge: 9 years, $360 million

It's hard to have a better walk year than Aaron Judge did in 2022 with the Yankees. Winning the AL MVP Award is a great way to add leverage to contract negotiations. The same could be said about him breaking the AL single-season home run record by slugging 62 dingers.

That led to Judge getting the richest contract in Yankees history (and one of the richest in MLB history). His $40 million average annual value is a record for position players, too. And as if this all wasn't enough, New York also named him team captain.

Injuries limited him to 106 games played in Year 1 of his new contract, but he made the most of the time he had on the field. Judge still found himself among the league leaders with 37 home runs.

2. Mookie Betts: 12 years, $365 million

Mookie Betts' 12-year deal with the Los Angeles Dodgers has him under contract through 2032. Acquiring him via trade with the Boston Red Sox immediately paid dividends in 2020. Despite the 60-game season, Betts finished second in NL MVP Award voting while also taking home a Gold Glove Award and a Silver Slugger Award, and winning the World Series.

The rest of his Dodgers tenure has been pretty darn good, too. Across 416 games played between 2021 and 2023, Betts has slashed .281/.373/.536. He's averaged 32 home runs, 36 doubles, 82 RBIs and 112 runs scored per season during this time.

1. Mike Trout: 12 years $426.5 million

Of course, Mike Trout is at the top of this list. Before Shohei Ohtani came along, a healthy Mike Trout was easily the best player in baseball. It made sense for the Los Angeles Angels to lock Trout down to a long-term extension that'd make him a career Angel. The bigger mistake they've made is not putting a team around him so Los Angeles could reach October with any kind of regularity (or, at all).

Trout's extension went into effect in 2019. That ended up being a typical year for him, which included 45 home runs, 104 RBIs and a 1.083 OPS, all of which helped him win his third AL MVP Award. It's been rough for the outfielder since then, mostly because he hasn't been able to stay on the field consistently.

After playing 53 of a possible 60 games in 2020, Trout has suited up for just 237 out of a possible 486 games because of various injuries. Hopefully, his age-32 campaign in 2024 will bring more health and at least 130 games played for the first time since his last MVP performance.

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