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The latest eye-popping contract in Major League Baseball was agreed to this week, with Rafael Devers set to sign an 11-year, $331 million extension with the Boston Red Sox. Devers’ deal ranks sixth all-time in MLB in terms of guaranteed money and is the second-largest agreed to this winter. Aaron Judge, the American League’s reigning Most Valuable Player, returned to the New York Yankees in December, agreeing to a nine-year contract worth $360 million. 

Judge chose the Yankees over the San Francisco Giants and the San Diego Padres, who reportedly made a late run at him. Originally, the Giants agreed to a contract with star infielder Carlos Correa for 13 years and $350 million. That contract would’ve been the fourth-largest in MLB history in terms of total guaranteed money. However, Correa’s deal with the Giants fell through after something reportedly came up during his physical, and the Mets quickly swooped in to sign him. Correa’s deal with the Mets — which has still not yet been officially announced — is for 12 years and $315 million, and it originally ranked in the top 10 of largest contracts in MLB history (but Devers’ deal kicked him out).

Judge’s $40 million average annual value establishes a new benchmark for position players. That record had previously belonged to Mike Trout ($35.54 million). Judge did not eclipse New York Mets pitchers Max Scherzer and Justin Verlander, each of whom has an AAV of $43.3 million annually, but he has plenty to celebrate. After all, this comes on the heels of him rejecting a seven-year offer worth around $213 million prior to the start of the season.

Here are the 10 richest contracts in MLB history, in terms of total value, according to Cot’s Contracts, as well as the top five in terms of average annual value.

Largest contracts (total money) in MLB history

  1. Mike Trout, Angels: $426.5 million (2019-30)
  2. Mookie Betts, Dodgers: $365 million (2021-32)
  3. Aaron Judge, Yankees: $360 million (2023-31)
  4. Francisco Lindor, Mets: $341 million (2022-31)
  5. Fernando Tatis, Padres: $340 million (2021-33)
  6. Rafael Devers, Red Sox: $331 million (2023-34)
  7. Bryce Harper, Phillies: $330 million (2019-31)
  8. Giancarlo Stanton, Marlins/Yankees: $325 million (2015-27)
  9. Corey Seager, Rangers: $325 million (2022-31)
  10. Gerrit Cole, Yankees: $324 million (2020-28)
  11. Carlos Correa, Mets: $315 million (2023-34)

Highest average annual value (AAV) in MLB history

  1. Max Scherzer, Mets: $43.33 million (2022-24)
  2. Justin Verlander, Mets: $43.33 million (2023-24)
  3. Aaron Judge, Yankees: $40 million (2023-31)
  4. Jacob deGrom, Rangers: $37 million (2023-27)
  5. Gerrit Cole, Yankees: $36 million (2020-28)

It’s worth noting that four of those five contracts have been signed in the past two offseasons. Indeed, Verlander, deGrom and Judge all signed last month.

Judge’s blockbuster deal comes on the heels of an historic season. He homered 62 times, establishing new single-season home run records for both the AL and the Yankees. Roger Maris had previously held both records after launching 61 home runs during the 1961 season. Devers’ deal, meanwhile, is the largest in Red Sox history.

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