The longest contracts in baseball history

April 7th, 2025

When Juan Soto agreed to a 15-year, $765 million deal with the Mets, it set a new standard for the longest pact in MLB history.

There have now been 29 MLB contracts totaling 10 years or longer, the latest being the 14-year, $500 million extension Vladimir Guerrero Jr. reached with the Blue Jays early in the 2025 campaign.

Here's a look at every deal of 10-plus years in MLB history.

Juan Soto, OF, Mets: 15 years, $765 million (2025-39)

Shortly after reaching free agency following the 2024 season, it was clear that Soto was going to shatter records with a free-agent contract. After helping lead the Yankees to the World Series and finishing third in AL MVP voting in his lone year in the Bronx, Soto landed the largest contract in MLB history, both in terms of years and total dollars. Just 26 years old at the time of the deal, Soto owned a career .285/.421/.532 line with 201 home runs. Soto's contract was earth-shattering not just from the sheer years and dollars of the deal but also from the perspective of him switching from one New York team to the other.

, 1B, Blue Jays: 14 years, $500 million (2026-39)

Guerrero seemed bound for the open market when eligible following the 2025 season, especially after his self-imposed deadline came and went without a new deal. At that point, Guerrero announced that the Blue Jays would ¡°have to compete with 29 more teams¡± in order to re-sign him. Things didn¡¯t quite play out that way: The two sides hammered out a historic extension to keep Guerrero in Toronto until 2039. A year after one of his best seasons -- he slashed .323/.396/.544 with a 167 OPS+ in 2024 -- Guerrero cashed in, inking the largest contract in Blue Jays franchise history as well as the largest extension in MLB history.

, SS, Padres: 14 years, $340 million (2021-34)

Tatis wasn't set to become a free agent until after the 2024 season and wasn't even eligible for arbitration at just 22 years of age, but San Diego clearly saw that it needed to ensure that he stayed a Padre for more than a decade to come. His extension, agreed upon as pitchers and catchers reported to Spring Training, kicked in immediately for 2021 and reportedly contains a no-trade clause -- another signal that he's not going anywhere. The Dominican native placed fourth in the 2020 National League MVP Award vote and had already racked up 39 career homers when he agreed to the extension, the most by any primary shortstop within his first 150 career games.

, CF, Mariners: 13 years, $210 million (2023-35)

The Mariners and J-Rod finalized a massive extension that guaranteed the rookie star at least 13 years and $210 million, but with a club option, could max out at 18 years and $470 million. The base salary of Rodr¨ªguez's deal is $120 million over eight years, after which the club can exercise an option of either eight or 10 years that would push the total value to between $320 million and $470 million, depending on where he finishes in MVP voting during the first eight years. If Seattle was to decline its club option after the first eight-year term, Rodr¨ªguez would have a player option for five years and $90 million.

, OF, Phillies: 13 years, $330 million (2019-31)

At the time it was signed, Harper¡¯s contract was tied for the longest in MLB history and set records for the most money and years given to any free agent in North American professional sports history. Harper's deal shattered Phillies records for free-agent contracts -- the team¡¯s prior longest FA deal was six years (Jim Thome), and the highest total value they¡¯d given a free agent was $120 million (Cliff Lee). He won an NL MVP Award (his second) in his third year with the Phillies and helped the team reach the World Series in 2022.

, OF, Marlins: 13 years, $325 million (2015-27)

Stanton¡¯s extension set a record for longest contract in MLB history, and at the time represented the largest total value as well, but he was not a free agent at the time. He played three seasons with the Marlins during the deal before being traded to the Yankees in December 2017 after winning the NL MVP Award.

, RHP, Dodgers: 12 years, $325 million (2024-35)

The Dodgers spared no expense in the 2023-24 offseason. Less than two weeks after inking Shohei Ohtani to the richest deal in MLB history -- more on that below -- the Dodgers handed Yamamoto the longest and most lucrative contract for any pitcher. Why did a hurler who has never proven himself at the Major League level demand such a high price? Because Yamamoto, at just 25 years old, was already a three-time winner of the Sawamura Award (Nippon Professional Baseball's equivalent to the Cy Young Award) and led NPB's Pacific League in wins, ERA and strikeouts in each of the previous three seasons. He went 49-16 with a 1.44 ERA and tallied 580 strikeouts during that span.

, OF, Dodgers: 12 years, $365 million (2021-32)

The Red Sox traded Betts and southpaw David Price to the Dodgers in a blockbuster deal following the 2019 season, in large part because many expected Betts to test the free-agent market following the 2020 campaign. But Los Angeles¡¯ front office was able to hammer out a massive extension right as the shortened 2020 season began, adding on to the record one-year, $27 million contract that Betts and the Red Sox agreed to in January of 2020 in order to avoid arbitration. The addition paid immediate dividends for the Dodgers. Betts was instrumental in leading Los Angeles to the 2020 World Series championship -- the franchise's first since 1988. He helped the team win another title in 2024.

, SS, Royals: 11 years, $288.7 million (2024-34)

Fresh off becoming the first Royals player to produce a 30/30 campaign in 2023, Witt reached a deal that could keep the former No. 2 overall Draft pick in a Kansas City uniform through 2037 if all three of his club options are exercised. Worth $288.7 million in guaranteed money, the deal shattered the record for the richest contract in Royals history.

, 3B, Padres: 11 years, $350 million (2023-33)

This was Machado's second contract totaling 10 years or longer. His previous deal with the Padres, a 10-year, $300 million pact signed in free agency prior to the 2019 season, gave him the ability to opt out at the end of 2023, but San Diego made sure the superstar third baseman will be staying in a Padres uniform through 2033.

Rafael Devers, 3B, Red Sox: 11 years, $331 million (2023-33)

While his former teammate Xander Bogaerts left the Red Sox on an 11-year deal, Devers chose to stay in Boston on an 11-year deal of his own. The $331 million extension that the 2018 World Series champion, 2021 Silver Slugger and two-time All-Star signed is even larger than the $280 million deal Bogaerts inked with the Padres in free agency. It's also a franchise-record contract for the Red Sox and one of the largest extensions in MLB history.

, SS, Padres: 11 years, $280 million (2023-33)

After four All-Star seasons and two World Series championships with the Red Sox, Bogaerts landed a free-agent deal with San Diego that was nearly identical to the deal fellow star free agent shortstop Trea Turner struck with the Phillies (11 years and $300 million) a couple of days earlier.

, SS, Phillies: 11 years, $300 million (2023-33)

Hitting the open market after back-to-back All-Star seasons, Turner struck the fifth free-agent deal of $300 million or more and the 20th overall contract (including FA signings and extensions) of 10-plus years in MLB history. The deal reunited Turner with Bryce Harper, his teammate with the Nationals before Harper left to sign his own megadeal with the Phils after the 2018 season. With Turner as one of its centerpieces, Washington went on to win a World Series title the following year. Turner was dealt to the Dodgers with Max Scherzer at the 2021 Trade Deadline before reaching free agency at the end of 2022.

, SS, Rays: 11 years, $182 million (2022-32)

Franco's contract set a record for the largest deal in Rays history, surpassing the six-year, $100 million pact Evan Longoria signed after the 2012 season. It's also the largest deal in Major League Baseball history for a player with less than a year of service time. Franco made his MLB debut in 2021 and posted a .288 average with seven homers and a 129 OPS+ over 70 games for the Rays, finishing third in the American League Rookie of the Year Award race. His season included a 43-game on-base streak, tying Franco with Hall of Famer Frank Robinson (1956) for the longest in AL/NL history by a player 20 years old or younger.

, C, Dodgers: 10 years, $140 million (2025-34)
, RHP/DH, Dodgers: 10 years, $700 million (2024-33)
, SS, Mets: 10 years, $341 million (2022-31)
, SS, Rangers: 10 years, $325 million (2022-31)
, OF, Angels: 10 years, $360 million (2021-30)
, 3B, Padres: 10 years, $300 million (2019-28)
, 2B, Mariners: 10 years, $228.26 million (2014-23)
, 1B, Reds: 10 years, $225 million (2014-23)
, 1B, Angels: 10 years, $240 million (2012-21)
, 3B, Yankees: 10 years, $275 million (2008-17)
, SS, Yankees: 10 years, $189 million (2001-10)
, SS, Rangers: 10 years, $252 million (2001-10)
, OF, Yankees: 10 years, $23 million (1981-90)
Richie Zisk, OF, Rangers: 10 years, $2.75 million (1978-1987)
Wayne Garland, RHP, Guardians: 10 years, $2.3 million (1977-1986)

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