We've seen some massive free-agent deals signed in recent offseasons, but Aaron Judge set a new standard when he reached a nine-year, $360 million deal with the Yankees at the 2022 Winter Meetings.
The previous record for the largest free-agent deal in MLB history belonged to Bryce Harper, who signed a 13-year, $330 million contract with the Phillies in 2019.
Judge's $40 million average annual value is also the highest for a position player and third-highest overall for an MLB free agent.
Here are the 10 biggest free-agent contracts in MLB history, both by total value and average annual value.
(Note: These don't include contract extensions where the player didn't actually become a free agent, like the 12-year, $426.5 million extension Mike Trout signed with the Angels on March 20, 2019.)
1) Aaron Judge, Yankees: 9 years, $360 million (2023-31)
Judge bet on himself when he declined the Yankees’ $213.5 million extension offer shortly before Opening Day in 2022, and it paid off in a big way. The 6-foot-7 outfielder had arguably the greatest free-agent walk year of all time, winning the AL MVP Award after setting an AL record with 62 homers and flirting with the Triple Crown. Despite serious overtures from the hometown Giants, Judge opted to return to the Yankees and set another record in the process, reaching the largest free-agent contract, in terms of total value, in MLB history.
2) Bryce Harper, Phillies: 13 years, $330 million (2019-31)
Harper's impending free agency defined his final season with the Nationals and dominated headlines all the way into the second week of Spring Training games, and a number of factors collaborated along the way to get Bryce to the top of this list. At the time, his deal was the largest free-agent contract in the history of the four major North American professional sports. Harper won his second career National League MVP Award in 2021 and led the Phillies to a World Series appearance in 2022, earning NLCS MVP honors along the way.
3) Corey Seager, Rangers: 10 years, $325 million (2022-31)
Seager earned his historic deal on the heels of slashing .306/.394/.521 with 16 home runs, 57 RBIs and a .915 OPS in 95 games for the Dodgers in 2021. That came one year after finishing ninth in 2020 National League MVP voting and earning MVP honors in both the NLCS and World Series en route to Los Angeles' title run. Along with his pair of postseason MVP Awards, Seager was also the 2016 NL Rookie of the Year and he was a two-time All-Star before signing his historic deal at the age of 27.
4) Gerrit Cole, Yankees: 9 years, $324 million (2020-28)
With Cole’s deal setting a record for pitchers, both of the top two free-agent deals by total value were given to No. 1 overall picks. Cole was taken first overall by the Pirates in 2011, while Harper was first overall in ‘10. Cole’s nine years are also the second most for any pitcher contract, trailing only Wayne Garland’s 10-year contract in the 1970s, in a far different era of free agency.
5) (tie) Manny Machado, Padres: 10 years, $300 million (2019-28)
Machado holds the distinction as being the first $300 million free agent in MLB history with the deal he inked with San Diego. An elite offense/defense two-way player, Machado finished among the top three in the NL MVP race twice over his first four seasons with San Diego and led the club to a 2022 NLCS appearance.
5) (tie) Trea Turner, Phillies: 11 years, $300 million (2023-33)
On the heels of a World Series appearance in 2022, the Phillies reeled in another big free-agent fish and filled their hole at shortstop by striking a $300 million deal with Turner, reuniting the speedster with his good friend and former Nationals teammate, Harper.
It marked the second straight offseason the Dodgers saw a shortstop leave their team in free agency for a contract worth at least $300 million with another club, as Turner followed Seager out the door. A two-time All-Star and 2019 World Series champion with the Nats, Turner hit .298 with 21 homers and 27 steals for the Dodgers in 2022.
7) Xander Bogaerts, Padres: 11 years, $280 million (2023-33)
Bogaerts truly began fulfilling the potential the Red Sox saw in him when they signed him as a 16-year-old out of Aruba when he had a breakout season in 2018. From 2018-22, the four-time All-Star slashed .301/.373/.508 with 105 homers while racking up 23.3 Baseball Reference wins above replacement for Boston.
Bogaerts' finest season so far came in 2019, when he posted a .939 OPS with 33 homers and 117 RBIs. But after winning two World Series championships with the Red Sox, the 30-year-old shortstop landed a massive deal with the Padres as San Diego continued a trend of making major acquisitions to win a World Series title of its own.
8) Alex Rodriguez, Yankees: 10 years, $275 million (2008-17)
In the middle of Game 4 of the 2007 World Series, Rodriguez's agent, Scott Boras, announced that A-Rod would be opting out of the final three years of his contract with the Yankees. (This was the contract he had originally signed with the Rangers prior to the '01 season, which carried over to New York when he was traded in '04.) The timing created a torrent of controversy, and it seemed like Rodriguez's tenure with the Yankees was over. Rodriguez would later call the opt-out a "huge debacle" and a "mistake that was handled extremely poorly."
Seeking to repair the relationship and re-open negotiations, A-Rod approached the Yankees through a Goldman Sachs managing director, and the two sides were able to work out a new deal in mid-December. That deal was the richest free-agent contract in MLB history. Rodriguez would go on to lead the Bronx Bombers to their 27th World Series championship in 2009. "All along," A-Rod said after reaching his new deal, "I knew I wanted to be a Yankee."
9) Alex Rodriguez, Rangers: 10 years, $252 million (2001-10)
Rodriguez's first free-agent megadeal -- the one he signed with the Rangers before the 2001 season -- ranks right behind his one with the Yankees. It pried him away from the Mariners at age 25, and at the time completely shattered the record for the largest free-agent contract, more than doubling Mike Hampton's $121 million deal with the Rockies that had been completed just days before Rodriguez's agreement was reached. In fact, it also doubled the largest professional sports contract to that point, Kevin Garnett's $126 million contract with the NBA's Timberwolves signed in 1997.
A-Rod played only the first three seasons of that contract in Texas before he was traded to the Yankees, but for his part, he lived up to the deal. Rodriguez averaged 52 home runs and 132 RBIs with the Rangers -- leading the American League in homers all three years -- with a 1.011 OPS from 2001-03. He won the AL MVP Award in '03. Rodriguez kept up the pace after he was traded to New York, winning two more MVP Awards in '05 and '07 (although his postseason struggles at times caused a lot of consternation among Yankees fans).
10) (tie) Anthony Rendon, Angels: 7 years, $245 million (2020-26)
Rendon was considered the best position player on the free-agent market after the 2019 season, and he got paid like it. He became just the sixth player to be an All-Star for a team that won the World Series, then leave in free agency that offseason. Rendon’s $35 million average annual value is the highest ever for a third baseman.
10) (tie) Stephen Strasburg, Nationals: 7 years, $245 million (2020-26)
When Strasburg opted out of his existing contract after winning the 2019 World Series, he still had $100 million due to him over four years. It turned out to be a highly lucrative decision. While Strasburg appeared to be far from certain to opt out when the season began, he proceeded to produce arguably his finest year, leading the NL in innings (209) and wins (18), posting a 3.32 ERA and 251 strikeouts while finishing fifth in the Cy Young Award race. He then put together one of the more spectacular postseason runs in history, culminating in a World Series MVP Award. Unfortunately for the Nats, Strasburg has made just eight starts and recorded a 6.89 ERA through the first three years of his seven-year contract.
Total value isn't the only way to look at player contracts, as the length of the deal also matters. Here's a list of the biggest MLB free-agent contracts by the amount they were worth per year.
Top 10 free-agent contracts by average annual value
1t. Max Scherzer, Mets: $43,333,333 (2022-24)
1t. Justin Verlander, Mets: $43,333,333 (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)
6t. Stephen Strasburg, Nationals: $35 million (2020-26)
6t. Anthony Rendon, Angels: $35 million (2020-26)
8. Trevor Bauer, Dodgers: $34 million (2021-23)
9. Zack Greinke, D-backs: $34,416,666 (2016-21)
10. Carlos Correa, Twins: $33,333,333 (2023-28)
10. Corey Seager, Rangers: $32.5 million (2022-31)