MLB
On this page, we will examine the largest contracts in MLB history, and the biggest winners and losers in MLB free-agency history.
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​Top 10 LARGEST CONTRACTS IN MLB HISTORY (As of 2025)
*Not including contract extensions*
10. Xander Bogaerts
Team: San Diego Padres (SS, 2B, 3B)
Contract: 11 years, $280 million (2023-2033)
Entered age-30 season in 2023
​Signed by the Red Sox as a 16-year-old out of Aruba, Bogaerts endured some inconsistency early in his career before breaking out in 2018. That season marked the start of a five-year stretch in which he slashed .301/.373/.508 with 105 home runs, produced 23.3 WAR, and earned three All-Star selections. He would leave the Red Sox after the 2022 season to sign a massive deal with the Padres. As a Padre Bogaerts has struggled to get back to his Red Sox form, dealing with injuries.
9. (Tie) Trea Turner
Team: Philadelphia Phillies (SS, 2B, OF)
Contract: 11 years, $300 million (2023- 2033)
Entered age-30 season in 2023
​Coming off their 2022 World Series run, the Phillies filled their shortstop vacancy by signing Turner to a $300 million contract, reuniting the speedy star with close friend and former Washington Nationals teammate Bryce Harper. Turner, a two-time All-Star and 2019 World Series champion with the Nationals, hit .298 with 21 home runs and stole 27 bases for the Dodgers in 2022.
8. (Tie) Manny Machado
Team: San Diego Padres (3B, SS)
Contracts: 10 years, $300 million (2019-2028)
Entered age-26 season in 2019
By signing with San Diego, Machado became the first player in MLB history to land a $300 million free-agent deal. Machado, a standout both offensively and defensively, finished in the top three of NL MVP voting twice during his first four seasons with San Diego and helped lead the team to the 2022 NLCS.
7. Gerrit Cole
Team: New York Yankees (SP)
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Contract: 9 years, $324 million (2020-2028)
Entered age-29 season in 2020
At the time, Cole’s contract set a record for pitchers and became the second $300-plus million deal awarded to a former No. 1 overall draft pick, following Bryce Harper’s. During the 2023 season, Cole won his first career Cy Young Award as a member of the Yankees.
6. (Tie) Yoshinobu Yamamoto
Team: Los Angeles Dodgers (SP)
Contract: 12 years, $325 million
Entered age-25 season in 2023
Not only did the Dodgers land superstar Shohei Ohtani, but they also secured the best pitcher available in 2023 free agency. Prior to joining the Dodgers, Yamamoto dominated Nippon Professional Baseball, winning three consecutive Eiji Sawamura Awards and earning a pitching Triple Crown with the Orix Buffaloes. In 2021, he posted an 18-5 record with a 2.35 ERA and 206 strikeouts. Yamamoto followed that up with two no-hitters in 2022 and was named the Pacific League Most Valuable Player in 2023, leading the league in wins, strikeouts, and ERA. With his $325 million deal, Yamamoto set the record for the highest guaranteed payout ever given to a pitcher.
5. (Tie) Corey Seager
Team: Texas Rangers (SS)
Contract: 10 years, $325 million (2022-2031)
Entered age 28 season in 2022
Before signing with the Rangers, Seager played 95 games for the Dodgers in 2021, slashing .306/.394/.521 with 16 home runs, 57 RBIs, and a .915 OPS. A year earlier, he had placed ninth in the 2020 National League MVP race and earned MVP honors in both the NLCS and World Series, helping Los Angeles secure the championship. Prior to joining the Rangers, Seager had also won the 2016 Rookie of the Year Award and was a two-time All-Star. In 2023, he would help lead the Rangers to win their first World Series title, earning MVP honors once again.
4. Bryce Harper
Team: Philadelphia Phillies (1B, OF)
Contract: 13 years, $330 million (2019-2031)
Entered age-26 season in 2019
​Harper, who had emerged as one of the best players in the game with the Nationals and was the top free agent available in 2019, signed a mega deal with their NL East rivals, the Phillies, breaking headlines all the way into the second week of spring training. At the time, his contract stood as the biggest free agent signing in the history of the four major North American professional sports leagues. In 2021, Harper won his second NL MVP Award and helped lead the Phillies to the World Series in 2022, earning NLCS MVP honors during the playoffs.
3. Aaron Judge
Team: New York Yankees (OF)
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Contract: 9 years, 360 million (2023-2031)
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Entered age-31 season in 2023
One day after Jon Heyman mistakenly reported that Aaron Judge had signed with the San Francisco Giants, Judge made it clear he wasn't going anywhere, agreeing to a monster deal to stay in pinstripes in 2022. In the first year of his new contract, Judge had an offensive explosion, setting a new home run record with 62 homers and earning consideration for the batting Triple Crown Award, ultimately winning the AL MVP Award. Judge went on to win back-to-back AL MVP Awards in 2024 and 2025.
2. Shohei Ohtani
Team: Los Angeles Dodgers (DH, SP)
Contract: 10 years, $700 million (2024-2033)
Entered age-29 season in 2024
After electrifying the league with the Los Angeles Angels as a two-way player (both starting pitcher and designated hitter), no one could have predicted the massive contract Ohtani would secure in the 2023 free agency. Many had estimated his contract would fall between $500 and $600 million, but even that proved to be an underestimate. Ohtani shattered the record for guaranteed money on a new contract, including $680 million in deferrals set for 2034-2043. In his debut season with the Dodgers, Ohtani made history by hitting 50 home runs and stealing 50 bases, earning his second MVP Award and helping lead the team to a World Series title. Between 2023 and 2025, Ohtani dominated, winning three straight NL MVPs Awards.
1. Juan Soto
Team: New York Mets (OF)
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Contract: 15 years, 765 million (2025-2039)
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Entered age-26 season in 2025
During the 2024 offseason, the Mets outbid their cross-town rivals, the Yankees, to sign Juan Soto to a record-breaking deal. After an incredible year with the Bronx Bombers, it was reported that the Yankees offered Soto a 16-year, $760 million deal, but Soto ultimately chose to join the Mets. At only 26 years of age, Soto has already earned four All-Star selections, five Silver Slugger Awards, two MVP finalist nods, and a World Series title (with the Nationals). Heading into his first season with the Mets, Soto boasts a career slash line of .285/.421/.532 with a .953 OPS, averaging 35 home runs and 102 RBIs per 162 games over his seven-year career.
Biggest winners and losers in MLB free agency history
Winners
Arizona Diamondbacks (1998-1999)
Key Signing:
Pitcher Randy Johnson (4 years, $52 million)
Results:
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Won four straight CY Young Awards (1999-2002)
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Won CO-MVP of 2001 World Series
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Helped win the franchise's first World Series
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Threw 1,030 innings, struck out 1,417 batters, and maintained a 187 ERA+ over the four-year period
New York Yankees (2008-2009)
Key signings:
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Pitcher CC Sabathia (7 years, $161 million)
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Pitcher A.J. Burnett (5 years, $82.5 million)
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Mark Teixeira (1B) (8 years, $180 million)
Results:
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Helped win the 2009 World Series
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Sabathia recorded multiple top five finishes in Cy Young Award voting
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Mark Teixeira finished second in AL MVP voting in 2009
Texas Rangers (2021-2022)
Key Signings:
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Marcus Semien (2B) (7 years, $175 million)
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Corey Seager (SS) 10 years, $325 million)
Results:
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Helped win the franchise's first World Series in 2023
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Seager and Semien combined for more than 14 WAR during the 2023 regular season
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Seager delivered an outstanding postseason performance and earned World Series MVP honors in 2023
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In total, the Rangers’ free-agent acquisitions generated 23.3 WAR for the championship roster
Losers
Colorado Rockies (2021-2022)
Worst signing:
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Khris Bryant (3B, OF, 1B) - (7 years, $182 million)
Results:
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The Rockies were not a contending team when they signed Bryant
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In only four seasons playing for the Rockies, Bryant has played 170 games mainly due to back, finger, and foot injuries.
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His batting average dropped from .279 with the Chicago Cubs to .244, while his OPS fell from .886 to.695.
Los Angeles Angels (2019-2020)
Worst Signing:
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Anthony Rendon (3B, 2B) (7 years, $245 million)
Results:
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After winning the World Series with the Washington Nationals, Rendon's performance had declined significantly.
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Rendon had missed almost two whole seasons due to mainly hamstring, wrist, and back injuries
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His batting average fell from .290 with the Nationals to .242, and his OPS dropped from .859 to .717
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Rendon and the Angels agreed to restructure his contract, ending Rendon's terrible tenure with the Angels​
Boston Red Sox (2010-2011)
Worst Signing:
Carl Crawford (OF) (7 years, $142 million)
Results:
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Crawford would only play 161 games in two seasons, mainly due to hip, wrist and shoulder injuries
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Crawford produced 35.6 WAR over nine seasons with the Rays, but managed only 0.9 WAR in two seasons with the Red Sox
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In 2012, Crawford was traded to the Los Angeles Dodgers, but Boston still had to pay a significant amount of his remaining salary
