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The latest eye-popping contract in Major League Baseball was agreed to this month, with Manny Machado reportedly signing an 11-year, $350 million extension with the San Diego Padres. Machado's deal ranks fourth all-time in MLB in terms of guaranteed money, behind Aaron Judge's blockbuster signing earlier 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. 

Machado's deal, which comes weeks before the launch of the 2023 season, will keep him in San Diego likely until the end of his career. He signed with the Padres on a 10-year, $300 million deal prior to the 2019 season, but there was an opt-out on his deal after this coming season.

Judge chose the Yankees over the San Francisco Giants and the San Diego Padres, who reportedly made a late run at him. Carlos Correa was originally slated to join the top 10 on the list of biggest MLB contracts. He agreed to a $350 million deal with the Giants in December, but the contract was never signed after something came up in Correa's physical. Correa then agreed to a $315 million deal with the Mets that never came to fruition, and he instead ended up getting a $200 million deal from the Twins.

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. Manny Machado, Padres: $350 million (2023-33)
  5. Francisco Lindor, Mets: $341 million (2022-31)
  6. Fernando Tatis, Padres: $340 million (2021-33)
  7. Rafael Devers, Red Sox: $331 million (2023-34)
  8. Bryce Harper, Phillies: $330 million (2019-31)
  9. Giancarlo Stanton, Marlins/Yankees: $325 million (2015-27)
  10. Corey Seager, Rangers: $325 million (2022-31)

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.