Cha-Ching! The Highest-Paid Players in MLB History
Yankees fans booed Joe DiMaggio to start the 1938 season, even though a year earlier he hit .346 with career highs in hits (215), home runs (46), RBIs (167), runs (151), total bases (418) and slugging percentage (.673).
Big-league players didn’t have a lot of bargaining power at that time, so DiMaggio was viewed negatively when he argued about his worth. Team owner Jacob Ruppert drew a line with a $10,000 salary increase from $15,000 from $25,000, and did all the Joltin’ to Joe by publicly criticizing him.
Rest assured, DiMaggio wouldn’t even recognize modern-day salaries, which have grown exponentially. Players often rake in $10,000-plus per at-bat.
According to Forbes, MLB salaries totaled over $4 billion in the five full seasons following 2016 (not including the 2020 pandemic-shortened campaign).
The following are the largest contracts in Major League Baseball history. But don’t delay, because the list of the highest-paid baseball players is an ever-changing one.
The Largest Contracts in MLB History
(Via Spotrac; contract values do not include proration with the shortened 2020 season)
1. Mike Trout, Los Angeles Angels – $426.5M (12 years)
Years: 2019-30; Average Annual Salary: $35,541,667; Signing Age: 27
Trout’s contract, signed in March 2019, added two years to the outfielder’s existing deal with the Angels and easily remains the highest in MLB history. The amount was over $100 million higher than Bryce Harper’s then-No. 1 deal (now No. 5) signed just weeks earlier.
2. Mookie Betts, Los Angeles Dodgers – $365M (12 years)
Years: 2021-32; Average Annual Salary: $30,416,667; Signing Age: 27
After trading for Betts from the Boston Red Sox in February 2020, the Dodgers inked the outfielder to a contract extension in July right before the start of the pandemic-delayed season. It included an MLB-record $65 million signing bonus.
3. Aaron Judge, New York Yankees – $360M (9 years)
Years: 2023-31; Average Annual Salary: $40,000,000; Signing Age: 30
Judge bet on himself in 2022, turning down a seven-year, $213.5-million deal before the season and accepting this megadeal after hitting an AL record-tying 62 home runs. Cha-ching!
4. Manny Machado, San Diego Padres – $350 (11 years)
Years: 2023-33; Average Annual Salary: $31,818,182; Signing Age: 30
This is the first of Machado’s two appearances on this list. This massive extension overwrites the 10-year, $300 million deal the star third baseman signed with the Padres in 2019. The deal came down after Machado announced he intended to opt out of the final five years (and $150 million) of the original contract after preliminary negotiations on an extension broke down.
5. Francisco Lindor, New York Mets – $341M (10 years)
Years: 2022-31; Average Annual Salary: $34,100,000; Signing Age: 27
Lindor agreed to a contract extension in March 2021, just over two months after the Mets acquired the shortstop from Cleveland. With $50 million in deferred compensation, the deal will keep on giving through annual $5 million payments from 2032-41.
6. Fernando Tatis Jr., San Diego Padres – $340M (14 years)
Years: 2021-34; Average Annual Salary: $24,285,714; Signing Age: 22
MLB teams have increasingly sought to sign younger players to long-term contracts at the service-time level, but Tatis’ shattered previous deals. He was 22 in February 2021 when extended to baseball’s longest contract in years (14).
7. Bryce Harper, Philadelphia Phillies – $330M (13 years)
Years: 2019-31; Average Annual Salary: $25,384,615; Signing Age: 26
Before Harper’s contract was surpassed by Trout in the top-this spending spree prior to the 2019 season, it bettered Manny Machado’s then-record total (now No. 9) just one week earlier. It still ranks highest among baseball free agent contracts (non-extensions).
T8. Giancarlo Stanton, Miami Marlins – $325M (13 years)
Years: 2015-27; Average Annual Salary: $25,000,000; Signing Age: 25
After signing baseball’s then-richest contract following the 2014 season, Stanton played three more years with the Marlins before they traded him to the New York Yankees. While ridding themselves of the final 10 years of the deal, the Marlins agreed to pay $30 million, which will be spread across 2026-28.
T8. Corey Seager, Texas Rangers – $325M (10 years)
Years: 2022-31; Average Annual Salary: $32,500,000; Signing Age: 27
Seager and the Rangers beat the start of the lockout in December 2021 with the second-highest free agent contract in major league history. The Rangers agreed to a seven-year, $175 million contract with Marcus Semien just 24 hours earlier, so they had a half-billion dollars worth of middle infield deals in a two-day span.
10. Gerrit Cole, New York Yankees – $324M (9 years)
Years: 2020-28; Average Annual Salary: $36,000,000; Signing Age: 29
Cole and the Yankees made the math easy with a $36 million base salary in each of the nine years of the free agent pitcher’s contract. Interestingly, Cole was the No. 1 pick in a 2011 draft top 10 that included Lindor, Anthony Rendon (tied for 14th below) and Trevor Bauer (his $45 million 2022 salary is a one-year high; Max Scherzer’s $43.3M is the overall average high for MLB contracts).
11. Rafael Devers, Boston Red Sox – $313.5M (10 years)
Years: 2024-33; Average Annual Salary: $31,350,000; Signing Age: 26
Let’s face it, the Red Sox had to keep someone. After losing stars Mookie Betts and Xander Bogaerts in recent seasons, Boston made sure Devers didn’t get away. Devers had actually previously agreed to a $17.5 million salary for 2023, so this was not an 11-year, $331-million extension as many reported. It was, however, easily the largest deal in franchise history.
12. Manny Machado, San Diego Padres – $300M (10 years)
Years: 2019-28; Average Annual Salary: $30,000,000; Signing Age: 26
To underscore salary escalation, consider this: In less than three years after Machado’s deal more than doubled the largest in Padres history, he’s gone from having baseball’s highest free-agent contract to fourth, from having the second-highest contract behind Stanton to ninth, and even dropped to No. 2 on the Padres behind Tatis despite being at $300 million. The Padres extended Machado in 2023 before this deal came to an end.
13. Trea Turner, Philadelphia Phillies – $300M (11 years)
Years: 2023-33; Average Annual Salary: $27,272,727; Signing Age: 30
The rich got richer as the 2022 NL champions signed another star to team with Bryce Harper, Kyle Schwarber, J.T. Realmuto, Nick Castellanos, Rhys Hoskins, Aaron Nola and Zack Wheeler.
14. Xander Bogaerts, San Diego Padres – $280 (11 years)
Years: 2023-33; Average Annual Salary: $25,454,545; Signing Age: 30
The spending spree continued at the 2022 Winter Meetings – in San Diego – when the hometown Padres stole Bogaerts away from the Boston Red Sox on yet another megadeal. Several of the top contracts on this list were signed in the 2022 offseason.
15. Alex Rodriguez, New York Yankees – $275M (10 years)
Years: 2008-17; Average Annual Salary: $27,500,000; Signing Age: 32
A-Rod re-signed with the Bronx Bombers after opting out of the final three seasons and $81 million of a landmark $252 million deal (now No. 12) with the Texas Rangers in 2001, which had more than doubled the previous record contract (Colorado Rockies 2000 free agent signee Mike Hampton’s deal for eight years, $121 million).
16. Nolan Arenado, Colorado Rockies – $260M (8 years)
Years: 2019-26; Average Annual Salary: $32,500,000; Signing Age: 27
Note: Traded to St. Louis Cardinals in 2021
17. Alex Rodriguez, Texas Rangers – $252M (10 years)
Years: 2001-10; Average Annual Salary: $25,200,000; Signing Age: 25
Note: Traded to New York Yankees in 2004
18. Miguel Cabrera, Detroit Tigers – $248M (8 years)
Years: 2016-23; Average Annual Salary: $31,000,000; Signing Age: 30
T19. Stephen Strasburg, Washington Nationals – $245M (7 years)
Years: 2020-26; Average Annual Salary: $35,000,000; Signing Age: 31
T19. Anthony Rendon, Los Angeles Angels – $245M (7 years)
Years: 2020-26; Average Annual Salary: $35,000,000; Signing Age: 29
T19. Robinson Cano, Seattle Mariners – $240M (10 years)
Years: 2014-23; Average Annual Salary: $24,000,000; Signing Age: 31
T19. Albert Pujols, Los Angeles Angels – $240M (10 years)
Years: 2012-21; Average Annual Salary: $24,000,000; Signing Age: 31
23. Joey Votto, Cincinnati Reds – $225M (10 years)
Years: 2014-23; Average Annual Salary: $22,500,000; Signing Age: 28
24. David Price, Boston Red Sox – $217M (7 years)
Years: 2016-22; Average Annual Salary: $31,000,000; Signing Age: 30
25 Clayton Kershaw, Los Angeles Dodgers – $215M (7 years)
Years: 2014-20; Average Annual Salary: $30,714,286; Signing Age: 25
Enjoy this? Subscribe to our mailing list to receive exclusive weekly content.