From record-setting extensions to the biggest MLB free agency moves, Boardroom rounds up the tallest stacks of cash changing hands this winter.
It’s now off-season. Winter meetings, backchanneling, Mattress Mack (supposedly) making it rain, Alex Anthopoulos trying to commit the legal equivalent of highway robbery, and the frantic rush by clubs trying to get some last-minute Christmas shopping done before all the shortstops are sold out are all to be expected.
Given the sheer amount of and extension candidates up for grabs this year, the stakes are extremely high. None looms greater than, who was crowned AL MVP as his contract with the New York Yankees officially expired.
In light of this, let’s list the largest contracts that MLB’s top players are signing this offseason, beginning with Aaron Judge’s historic Bronx jackpot.
Biggest Contracts of the 2022-23 MLB Offseason
Reflects the largest MLB contracts by total value to be signed since the end of the 2022 regular season as of Dec. 5. All dollar figures via .
Yankees OF Aaron Judge: $360,000,000
- Type: Extension
- Years: 9
- Free agency: 2032
Mets SS Carlos Correa: $315,000,000
- Type: Free agent
- Years: 12
- Free agency: 2035
NOTE: Correa had previously agreed to a 13-year, $350 million deal with the San Francisco Giants that was not finalized after an issue reportedly emerged with his medical evaluation.
Phillies SS Trea Turner: $300,000,000
- Type: Free agent
- Years: 11
- Free agency: 2034
Padres SS Xander Bogaerts: $280,000,000
- Type: Free agent
- Years: 11
- Free agency: 2034
Rangers SP Jacob deGrom: $185,000,000
- Type: Free agent
- Years: 5 (plus sixth-year club option)
- Free agency: 2027 or 2028
NOTE: Including the 2028 club option, the max value of deGrom’s deal with Texas is six years and $222 million.
Cubs SS Dansby Swanson: $177,000,000
- Type: Free agent
- Years: 7
- Free agency: 2030
Mets OF Brandon Nimmo: $162,000,000
- Type: Extension
- Years: 8
- Free agency: 2031
RP Edwin Diaz: $102,000,000
- Type: Extension
- Years: 5
- Free agency: 2028
NOTE: Diaz’s extension is the largest relief pitcher contract in MLB history by both total value and average annual value, and includes a $20,000,000 club option for 2028.
Cardinals C Willson Contreras: $87,500,000
- Type: Free agent
- Years: 5
- Free agency: 2028
Mets SP Justin Verlander: $86,666,666
- Type: Free agent
- Years: 2 (plus third-year vested option)
- Free agency: 2025 or 2026
NOTE: Including the 2025 option, the max value of Verlander’s deal with the Mets is three years and $121.666 million.
Mets SP Kodai Senga: $75,000,000
- Type: Free agent
- Years: 5
- Free agency: 2028
Cubs SP Jameson Taillon: $68,000,000
- Type: Free agent
- Years: 4
- Free agency: 2027
Blue Jays SP Chris Bassitt: $63,000,000
- Type: Free agent
- Years: 3
- Free agency: 206
1B Jose Abreu: $58,500,000
- Type: Free agent
- Years: 3
- Free agency: 2026
RP Robert Suarez: $46,000,000
- Type: Extension
- Years: 5
- Free agency: 2028
Giants OF Mitch Haniger: $43,500,000
- Type: Free agent
- Years: 3
- Free agency: 2026
1B Anthony Rizzo: $40,000,000
- Type: Extension
- Years: 2
- Free agency: 2025
NOTE: Rizzo’s contract includes a $6,000,000 club option for 2025, giving it a max value of three years and $46,000,000.
SP Zach Eflin: $40,000,000
- Type: Free agent
- Years: 3
- Free agency: 2026
SP Tyler Anderson: $39,000,000
- Type: Free agent
- Years: 3
- Free agency: 2026
Astros RP Rafael Montero: $34,500,000
- Type: Extension
- Years: 3
- Free agency: 2026
Guardians 1B Josh Bell: $33,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Red Sox RP Kenley Jansen: $32,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Twins C Christian Vazquez: $30,000,000
- Type: Free agent
- Years: 3
- Free agency: 2026
Mets SP Jose Quintana: $26,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Rangers SP Andrew Heaney: $25,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Giants SP Sean Manaea: $25,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
NOTE: Manaea can opt out after the 2023 season.
Giants SP Ross Stripling: $25,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Red Sox 3B Justin Turner: $21,700,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Dodgers SP Clayton Kershaw: $20,000,000
- Type: Extension
- Years: 1
- Free agency: 2024
SP Adam Wainwright: $17,500,000
- Type: Extension
- Years: 1
- Free agency: 2024
Cubs OF Cody Bellinger: $17,500,000
- Type: Free agent
- Years: 1
- Free agency: 2024
Red Sox RP Chris Martin: $17,500,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Phillies RP Matthew Strahm: $15,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
INF Aledmys Diaz: $14,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Angels RP Carlos Estevez: $13,500,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Dodgers SP Noah Syndergaard: $13,000,000
- Type: Free agent
- Years: 1
- Free agency: 2024
Nationals SP/RP Trevor Williams: $13,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Astros OF Michael Brantley: $12,000,000
- Type: Extension
- Years: 1
- Free Agency: 2024
SP Mike Clevinger: $12,000,000
- Type: Free agent
- Years: 1
- Free agency: 2024
Yankees RP Tommy Kahnle: $11,500,000
- Type: Free agent
- Years: 2
- Free agency: 2025
SP Matt Boyd: $10,000,000
- Type: Free agent
- Years: 1
- Free agency: 2024
Orioles SP Kyle Gibson: $10,000,000
- Type: Free agent
- Years: 1
- Free agency: 2024
Mets RP David Robertson: $10,000,000
- Type: Extension
- Years: 1
- Free agency: 2024
