The Biggest MLB Contracts Ever - Richest MLB Deals in History

In recent memory, the contracts that star MLB players have been receiving are eye-opening, to say the least.

Shohei Ohtani has made good on his Dodgers contract so far, though he's only 12 games into a deal that could keep him a Dodger for 1,620 of them, ultimately paying him $700 million by the time all the deferrals are paid out.

Let's count down the rest of the list of the 10 biggest contracts in MLB history.

• Fantasy baseball injury reports
• Fantasy baseball trade analyzer
• Daily MLB starting lineups for fantasy baseball
• Fantasy baseball BvP matchups data (Batter vs. Pitcher)
• Fantasy baseball PvB matchups data (Pitcher vs. Batter)
• Who should I start? Fantasy baseball player comparisons
• Fantasy baseball closer depth charts, bullpens, saves
• Fantasy Baseball live scoreboard, daily leaderboards

No. 8 (Tie) — Giancarlo Stanton, Miami Marlins, $325 million (13 years)

Nobody really expected Giancarlo Stanton to finish out his mega-extension with the Marlins when he signed it in November of 2014, but he only made it three seasons in! Even factoring in that the Marlins kicked in $30 million in future payments to the Yankees to facilitate the trade, they're ultimately paying just $60 million of the deal, with the Yankees writing the checks for the remainder.

Stanton has struggled to stay healthy as a Yankee, playing in just 549 of 870 possible games (63%) from 2018-23. He's been solid at the plate with a 122 wRC+, but ultimately has been worth just 8.4 fWAR due to his large proportion of time as the DH.

Giancarlo Stanton is still under contract for four more years, plus a Club Option with a $10 million in 2028. pic.twitter.com/qbRZrq1PYH

— Mike Maher (@mikeMaher) March 20, 2024

No. 8 (Tie) — Yoshinobu Yamamoto, Los Angeles Dodgers, $325 million (12 years)

By far the largest deal for any player without any prior MLB experience, the Dodgers, Yankees, and Mets all blew initial expectations out of the water in offering Yamamoto deals worth at least $300 million each. He ultimately chose to join Ohtani in Los Angeles, with the two combining for over $1 billion in commitments. It's far too early to evaluate this deal in any meaningful way, but Yamamoto has rebounded from his horrible start in Seoul to spin two scoreless five-inning outings.

Yoshinobu Yamamoto's deal includes a pair of opt-outs, sources tell ESPN.

Here are more details on the contract, which is pending a physical: 12 years, $325 million (which includes a $50 million signing bonus), no deferred money, an additional $50.6 million posting fee to Orix.

— Jeff Passan (@JeffPassan) December 22, 2023

No. 8 (Tie) — Corey Seager, Texas Rangers, $325 million (10 years)

It's foolish to act as if Seager has already made good on his massive contract, though the Rangers certainly wouldn't trade away his postseason heroics last year for, say, better performance in the twilight of his career. The nagging health issues that have plagued Seager continue to be a factor, as his MVP runner-up season could have been legendary if he'd played more than 119 games. But even with a so-so first year in Texas in 2022 and limited time in 2023, he's been what the Rangers have asked, with a 139 wRC+ and 10.7 WAR in the Lone Star State.

No. 7 — Bryce Harper, Philadelphia Phillies, $330 million (13 years)

Harper languished on the free-agent market until March 2019. You can't really blame him for eliminating all of the noise that another trip to the open market would create, instead taking a 13-year deal with no opt outs, even at a low AAV that could certainly lead to him being underpaid over the life of the contract.

So far, it certainly looks like that's the case. Harper's been nothing short of incredible as a Phillies player, locking up his second MVP in 2021 and compiling 18.9 fWAR, or 5.2 per 162 games. He's showing no signs of slowing down even after a position change to first base in his age-31 season.

Contract breakdown for Bryce Harper's deal with the Philadelphia Phillies, sources tell ESPN:

2019: $10M (plus $20M signing bonus)
2020: $26M
2021: $26M
2022: $26M
2023: $26M
2024: $26M
2025: $26M
2026: $26M
2027: $26M
2028: $26M
2029: $22M
2030: $22M
2031: $22M

— Jeff Passan (@JeffPassan) March 1, 2019

No. 6 — Fernando Tatis Jr., San Diego Padres, $340 million (14 years)

Easily the most tumultuous entry on this list, Tatis is in just the fourth year of his contract but has already dealt with a shoulder surgery, multiple wrist surgeries, a PED suspension, and a move to right field to accommodate Xander Bogaerts.

It's not shocking then that Tatis's performance and availability during his deal have been... erratic to say the least. In 2021, he was an excellent hitter and poor shortstop before his 2022 was completely wiped out by injury and the suspension. He came back in 2023 as a brilliant right fielder and above-average-but-not-great hitter, and he now looks to put together a monster season on both sides of the ball in 2024.

Here's the breakdown of Fernando Tatis Jr.'s 14-year, $340M contract, per source:

2021: $1M 2028: $25M
2022: $5M 2029: $36M
2023: $7M 2030: $36M
2024: $11M 2031: $36M
2025: $20M 2032: $36M
2026: $20M 2033: $36M
2027: $25M 2034: $36M

— Mark Feinsand (@Feinsand) February 22, 2021

No. 5 — Francisco Lindor, New York Mets, $341 million (10 years)

It feels as if Lindor's contract has flown under the radar as one of the best big deals in baseball. In his first three seasons of the deal, Lindor was worth 15.9 fWAR (5.3 per season), providing far more value than his $34.1 million AAV would demand to break even from an analytics perspective.

His slick fielding, switch-hitting heroics, and gregarious personality arguably make him the face of the Mets franchise, a fact that will become inarguable if Pete Alonso departs in free agency this coming offseason.

No. 3 (Tie) — Mike Trout, Los Angeles Angels, $360 million (10 years)

Very technically, Trout's contract is a 12-year, $426.5 million one, but that includes $66.5 million that he was already due from his previous extension; this deal tacked on $360 million and moved some money around. Trout won his third MVP in the first year of the deal but has struggled to stay healthy since; from 2020-23 onward, he played in just 290 of 546 (53%) games that the Angels played.

That said, Trout's been his usual self when able to be on the field; his wRC+ since the deal started is 167, and he's been worth just under 22 fWAR.

No. 3 (Tie) — Aaron Judge, New York Yankees, $360 million (9 years)

Nobody's ever holding a team hostage and saying they have to sign a player, but I think Yankees fans would have mutinied if Judge had signed in San Francisco or San Diego instead. From a pure baseball perspective, is paying a player coming off a virtually impossible to match $40 million a year from ages 31-39 a great move? Probably not in the long run, but the Yankees just couldn't let their superstar walk away.

In case you needed a better understanding of what Aaron Judge’s nine-year, $360 million contract with the Yankees means. That’s nearly…

$770,000 per week
$110,000 per day
$4,600 per hour
$76 per minute

🤯🤯🤯

(H/T @JoePompliano) pic.twitter.com/kBLCOzBR4V

— Sports Illustrated (@SInow) December 7, 2022

No. 2 — Mookie Betts, Los Angeles Dodgers, $365 Million (12 years)

We'll never know for sure if Betts really would have taken this deal if the Red Sox had offered it, or if the uncertainty surrounding COVID led him to accept it before he was set to hit free agency. But the Dodgers are certainly glad they were the ones to offer it, and Mookie has rewarded them handsomely.

Betts has more than made good on his end of the deal, as he's been arguably the best player in baseball since the day he signed it. He's been worth 21.9 fWAR and his wRC+ is 151, all while moving from right field to a right/second base hybrid, to now taking on shortstop for the first extended stretch in his career -- all on the wrong side of 30.

The Mookie Betts contract extension, which tacks 12 years and $365M onto his $27M salary (of which pro rata pay is $10M) this year, is stunning. While deferrals in the deal are expected, the sheer size of the number — $392M — illustrates how much the Dodgers believe in Betts.

— Jeff Passan (@JeffPassan) July 22, 2020

No. 1 — Shohei Ohtani, Los Angeles Dodgers, $700 million (10 years)

Even if you prefer to use the present value of Ohtani's massive contract, the ~$460 million in 2024 is still the largest deal in history by nearly $100 million.

As with Yamamoto, there's no sense in evaluating the merits of Ohtani's deal just a few weeks in. But the Dodgers are paying for more than just a player: they're paying for the biggest superstar in the league today, a player they can market in not one but two countries. They're paying for the right to say "Shohei Ohtani is ours, not anybody else's." Dodgers fans sure are happy they can say the same.

Shohei Ohtani’s new deal is the largest contract signed in North American sports history 😳 pic.twitter.com/2UqqImob86

— ESPN (@espn) December 9, 2023

More Fantasy Baseball Advice