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Biggest Contracts in MLB History: Ohtani, Judge, Trout, & More

Last Updated: December 15, 2023
From Bryce Harper and Mike Trout to Mookie, Machado, and beyond, Boardroom rounds up the biggest MLB bags of all time — check out baseball’s biggest numbers!

On Dec. 11, 2000, Alex Rodriguez signed a contract. Instead of sticking around and chasing World Series glory with his fair Seattle Mariners, however, he opted to join the last-place Texas Rangers. Why, you ask? Well, there were 252 million reasons over the course of what was to be the next 10 years.

More than two decades later, that A-Rod contract is still among the top 20 all-time in Major League Baseball by total value. He broke his own record with a $275 million deal with the New York Yankees in 2008; it would not be until Bryce Harper’s own intra-divisional blockbuster 11 years later that this financial championship belt changed waists.

Neither of these guys, however, can claim the No. 1 spot on the hallowed honor roll you’re about to see.

So, who tops the list of the biggest contracts in MLB history, and who’s nipping at his heels right behind.Check out Boardroom’s full rundown below.

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Biggest Contracts in MLB History: The Top 40

All dollar figures reflect total contract value as noted by Spotrac.

1. Los Angeles Dodgers P/DH Shohei Ohtani: $700,000,000

  • Type: Veteran extension
  • Years: 10 (2023-2033)
  • Average Annual Value (AAV): $70,000,000

Details of the record-setting deal continue to emerge at this time. Stay tuned to Boardroom for more information.

2.Angels OF Mike Trout: $426,500,000

  • Type: Veteran extension
  • Years: 12 (2019-30)
  • Average Annual Value (AAV): $35,541,667

This extension is the No. 3 largest contract in North American sports history behind Patrick Mahomes’ $450 million deal with the NFL’s Kansas City Chiefs and Lionel Messi’s deal with Inter Miami CF. Click here to read Boardroom’s deep dive into Trout’s record-setting Angels extension.

3. Dodgers OF Mookie Betts: $365,000,000

  • Type: Veteran extension
  • Years: 12 (2021-2032)
  • AAV: $30,416,667

Betts’ deal includes $120 in deferred money that pays out between 2033 and 2044. Click here to read Boardroom’s deep dive into Mookie’s contract with the Dodgers.

4. Yankees OF Aaron Judge: $360,000,000

  1. Type: Veteran extension
  2. Years: 9 (2023-31)
  3. AAV: $40,000,000

Click here to read Boardroom’s deep dive into Judge’s Yankees extension.

5. Padres 3B Manny Machado: $350,000,000

  • Type: Veteran extension
  • Years: 4 (2024-28)
  • AAV: $56,056,000

Click here to read Boardroom’s deep dive into Manny’s contract with the Padres.

6. Mets SS Francisco Lindor: $341,000,000

  • Type: Veteran extension
  • Years: 10 (2022-31)
  • AAV: $34,100,000

$50 million of Lindor’s contract is deferred at $5 million per year between 2032 and 2041. Click here to read Boardroom’s deep dive into Mr. Smile’s Mets extension.

7. Padres OF/SS Fernando Tatis Jr.: $340,000,000

  • Type: Pre-arbitration extension
  • Years: 14 (2021-34)
  • AAV: $24,285,714

This contract is the largest ever signed by a pre-arb player. Click here to read Boardroom’s deep dive on Tatis’ Padres extension.

8. Phillies OF Bryce Harper: $330,000,000

  • Type: Free agency
  • Years: 13 (2019-31)
  • AAV: $25,384,615

This deal previously held the record for the largest contract in MLB history before being surpassed by Mike Trout. Click here to read Boardroom’s deep dive into Harper’s contract with the Phillies.

t-9. Rangers SS Corey Seager: $325,000,000

  • Type: Free agency
  • Years: 10 (2022-31)
  • AAV: $32,500,000

Seager’s contract is the largest ever signed by an MLB free agent.

t-9. Yankees OF/DH Giancarlo Stanton: $325,000,000

  • Type: Veteran extension
  • Years: 5 (2022-27)
  • AAV: $43,031,940

Stanton’s deal was originally signed as a member of the Miami Marlins. Click here to read Boardroom’s deep dive into Giancarlo’s extension.

11. Yankees SP Gerrit Cole: $324,000,000

  • Type: Free agency
  • Years: 9 (2020-28)
  • AAV: $36,000,000

This contract is the largest in MLB history for a pitcher. Click here to read Boardroom’s deep dive into Cole’s contract with the Yankees.

12. Red Sox 3B Rafael Devers: $313,500,000

  • Type: Arbitration extension
  • Years: 10 (2024-33)
  • AAV: $31,350,000

This contract includes $75 million in deferred money to be paid between 2034 and 2043. Click here to read Boardroom’s deep dive on Devers’ Red Sox extension.

13. Phillies SS Trea Turner: $300,000,000

  • Type: Free agency
  • Years: 11 (2023-33)
  • AAV: $27,272,727

Click here to read Boardroom’s deep dive into Turner’s contract with Philly.

14. Padres SS Xander Bogaerts: $280,000,000

  • Type: Free agency
  • Years: 11 (2023-33)
  • AAV: $25,454,545

Click here to read Boardroom’s deep dive on Bogaerts’ Padres deal.

15. Yankees 3B/SS Alex Rodriguez: $275,000,000

  • Type: Veteran extension
  • Years: 10 (2008-17)
  • AAV: $27,500,000

16. Cardinals 3B Nolan Arenado: $260,000,000

  • Type: Arbitration extension
  • Years: 8 (2019-27)
  • AAV: $32,500,000

This contract was signed while Arenado was a member of the Colorado Rockies and includes $30 million in deferred money to be paid out between 2032 and 2041.

17. Rangers SS Alex Rodriguez: $252,000,000

  • Type: Free agency
  • Years: 10 (2001-10)
  • AAV: $25,200,000

18. Tigers DH Miguel Cabrera: $248,000,000

  • Type: Veteran extension
  • Years: 8 (2016-23)
  • AAV: $31,000,000

t-19. Nationals SP Stephen Strasburg: $245,000,000

  • Type: Free agency
  • Years: 7 (2020-26)
  • AAV: $35,000,000

This contract includes $80 million in deferred money to be paid out between 2027 and 2029.

t-19. Angels 3B Anthony Rendon: $245,000,000

  • Type: Free agency
  • Years: 7 (2020-26)
  • AAV: $35,000,000

22. Reds 1B Joey Votto: 10 years, $225,000,000
23. SP David Price: 7 years, $217,000,000 (signed with Red Sox)
24. Dodgers SP Clayton Kershaw: 7 years, $215,000,000
25. 1B/DH Prince Fielder: 9 years, $214,000,000 (signed with Tigers)
26. Braves 3B Austin Riley: 10 years, $212,000,000
27. SP Max Scherzer: 7 years, $210,000,000 (signed with Nationals)
28. Mariners OF Julio Rodriguez: 12 years, $209,300,000
29. SP Zack Greinke: 6 years, $206,500,000 (signed with Diamondbacks)
30. Twins SS Carlos Correa: 6 years, $200,000,000
31. Yankees SS Derek Jeter: 10 years, $189,000,000
32. Brewers OF Christian Yelich: 7 years, $188,500,000
33. Rangers SP Jacob deGrom: 5 years, $185,000,000
t-34. Twins C Joe Mauer: 8 years, $184,000,000
t-34. OF Jason Heyward: 8 years, $184,000,000 (signed with Cubs)
t-36. Rockies OF Kris Bryant: 7 years, $182,000,000
t-36. Rays SS Wander Franco: 11 years, $182,000,000
t-38. Yankees 1B Mark Teixeira: 8 years, $180,000,000
t-38. SP Justin Verlander: 7 years, $180,000,000 (signed with Tigers)
40. Cubs SS Dansby Swanson: 7 years, $177,000,000

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