From record-setting extensions to the biggest MLB free agency moves, Boardroom rounds up the tallest stacks of cash changing hands this winter.
The MLB offseason is here. That means winter meetings, backchanneling, Mattress Mack (presumably) making it rain, Alex Anthopoulos attempting the contractual equivalent of highway robbery, and the mad scramble by teams hoping to do some last-minute Christmas shopping before all the shortstops are sold out.
The stakes are especially high this year, too, given the sheer number of high-profile free agents and extension candidates on the board, with none looming larger than Aaron Judge, who was named AL MVP as his contract with the New York Yankees officially expired.
With that in mind, let’s round up the biggest MLB contracts the stars of the diamond are signing this offseason — starting with Aaron Judge’s historic Bronx jackpot.
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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 Spotrac.
Yankees OF Aaron Judge: $360,000,000
- Type: Extension
- Years: 9
- Free agency: 2032
Click here to read Boardroom’s deep dive on Judge’s contract extension with the Yankees.
Padres 3B Manny Machado: $350,000,000
- Type: Extension
- Years: 11
- Free agency: 2035
NOTE: Machado was four years into a contract with San Diego for 10 years and $300 million that has been superseded by this new deal.
Click here to read Boardroom’s deep dive on Machado’s contract extension with the Padres.
Red Sox 3B Rafael Devers: $331,000,000
- Type: Extension
- Years: 11
- Free agency: 2035
NOTE: Devers and the Red Sox had previously agreed to a $17.5 million salary number for 2023 to avoid arbitration; the 11-year extension begins in 2024.
Click here to read Boardroom’s deep dive on Devers’ contract extension with the Red Sox.
Phillies SS Trea Turner: $300,000,000
- Type: Free agent
- Years: 11
- Free agency: 2034
Click here to read Boardroom’s deep dive on Turner’s contract with the Phillies.
Padres SS Xander Bogaerts: $280,000,000
- Type: Free agent
- Years: 11
- Free agency: 2034
Click here to read Boardroom’s deep dive on Bogaerts’ contract with the Padres.
Twins 3B/SS Carlos Correa: $200,000,000
- Type: Extension
- Years: 6
- Free agency: 2029
NOTE: Correa had previously agreed to (1) a 13-year, $350 million deal with the San Francisco Giants and (2) a 12-year, $315 million deal with the New York Mets, neither of which were finalized after issues reportedly emerged with his medical evaluation.
Click here to read Boardroom’s deep dive on Correa’s contract with the Twins.
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.
Click here to read Boardroom’s deep dive on JdG’s contract with the Rangers.
Cubs SS Dansby Swanson: $177,000,000
- Type: Free agent
- Years: 7
- Free agency: 2030
Click here to read Boardroom’s deep dive on Swanson’s contract with the Cubs.
Mets OF Brandon Nimmo: $162,000,000
- Type: Extension
- Years: 8
- Free agency: 2031
Diamondbacks OF Corbin Carroll: $111,000,000
- Type: Extension
- Years: 8
- Free agency: 2031
Guardians 2B Andrés Giménez: $106,500,000
- Type: Extension
- Years: 7 (plus eighth-year team option)
- Free agency: 2030 or 2031
Mets 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. Click here to read Boardroom’s deep dive into the record-setting deal.
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.
Click here to read Boardroom’s deep dive on JV’s contract with the Mets.
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
Astros 1B Jose Abreu: $58,500,000
- Type: Free agent
- Years: 3
- Free agency: 2026
Mets INF Jeff McNeil: $50,000,000
- Type: Extension
- Years: 4
- Free agency: 2027
NOTE: McNeil’s contract includes a $13.75 million club option for 2028, giving it a max value of five years and $63.75 million.
Padres 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
Yankees 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.
Rays SP Zach Eflin: $40,000,000
- Type: Free agent
- Years: 3
- Free agency: 2026
Angels SP Tyler Anderson: $39,000,000
- Type: Free agent
- Years: 3
- Free agency: 2026
Giants OF Michael Conforto: $36,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Astros RP Rafael Montero: $34,500,000
- Type: Extension
- Years: 3
- Free agency: 2026
Rangers SP Nathan Eovaldi
Guardians 1B Josh Bell: $33,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Giants RP Taylor Rogers: $33,000,000
- Type: Free agent
- Years: 3
- Free agency: 2026
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
Red Sox 3B Rafael Devers: $17,500,000
- Type: Extension (to avoid arbitration in 2023)
- Years: 1
- Free agency: 2035 (see above)
Cardinals 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
Marlins 2B Jean Segura: $17,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Royals SP Jordan Lyles: $17,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
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Phillies RP Matthew Strahm: $15,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Padres RP Seth Lugo: $15,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Mets RP Adam Ottavino: $14,500,000
- Type: Extension
- 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
White Sox SP Mike Clevinger: $12,000,000
- Type: Free agent
- Years: 1
- Free agency: 2024
Padres 3B Matt Carpenter: $12,000,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Giants RP Luke Jackson: $11,500,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Yankees RP Tommy Kahnle: $11,500,000
- Type: Free agent
- Years: 2
- Free agency: 2025
Twins OF/DH Joey Gallo: $11,000,000
- Type: Free agent
- Years: 1
- Free agency: 2024
Dodgers DH J.D. Martinez: $10,000,000
- Type: Free agent
- Years: 1
- Free agency: 2024
Phillies RP Craig Kimbrel: $10,000,000
- Type: Free agent
- Years: 1
- Free agency: 2024
Red Sox SP Corey Kluber: $10,000,000
- Type: Free agency
- Years: 1
- Free agency: 2024
NOTE: Kluber’s contains an $11 million club option for 2024, giving the contract a max value of two years and $21 million.
Tigers 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
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