The longest contracts in baseball history

March 27th, 2024

When Fernando Tatis Jr. signed a 14-year extension with the Padres in 2021, it set a new standard for the longest pact in MLB history.

There have now been 27 MLB contracts totaling 10 years or longer, the latest being the 10-year, $140 million extension Will Smith signed with the Dodgers in March 2024.

Here's a look at each of these deals in reverse chronological order based on the year each contract will run through.

, 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.

, 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. Currently, the largest contract in MLB history by total value is Mike Trout's 12-year, $426.5 million deal with the Angels (signed in 2019). The base salary of Rodríguez'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, Rodríguez would have a player option for five years and $90 million.

, C, Dodgers: 10 years, $140 million (2025-34)

Closing out an already eventful offseason in Los Angeles, the Dodgers signed All-Star catcher Will Smith to a 10-year, $140 million extension on the eve of Opening Day in 2024. The deal is the longest contract signed by a backstop in Major League history, surpassing the nine-year deal the rival Giants gave to Buster Posey in 2013.

, 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.

, 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.

, RHP/DH, Dodgers: 10 years, $700 million (2024-33)

A one-of-a-kind player deserves a one-of-a-kind contract -- and that's exactly what Ohtani received. After six seasons with the Angels, during which he made three All-Star teams, won the 2018 AL Rookie of the Year Award and took home MVP honors in 2021 and 2023, Ohtani signed a 10-year deal worth $700 million, which is the most lucrative contract in Major League Baseball history, almost doubling the value of the previous largest free-agent deal, the nine-year, $360 million contract signed by Aaron Judge in 2022.

, 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)

With his former teammate Xander Bogaerts leaving Boston 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.

, 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.

, 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.

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

Harper’s contract was tied for the longest in MLB history before Tatis' extension, and it’s 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.

, SS, Mets: 10 years, $341 million (2022-31)

Lindor had one year remaining before free agency when the Mets acquired the superstar shortstop along with right-hander Carlos Carrasco from Cleveland in a six-player trade on Jan. 7, 2021. After months of negotiations, New York made certain that Lindor wouldn’t be making an early exit from Queens, inking him to a contract on the eve of Opening Day. The deal tacked on 10 years and $341 million to his existing $22.3 million contract for 2021.

, SS, Rangers: 10 years, $325 million (2022-31)

After seven seasons with the Dodgers that included an NL Rookie of the Year Award, two NL Silver Slugger Awards, two All-Star selections, an NLCS MVP Award and a World Series MVP Award, Seager left Los Angeles to ink one of the largest free-agent contracts in baseball history with the Rangers. Texas' deal with Seager came a day after the team reached a seven-year contract with another star infielder, Marcus Semien. The middle-infield duo was instrumental in the Rangers' 2023 World Series title.

, OF, Angels: 10 years, $360 million (2021-30)

Trout was set to become a free agent after the 2020 season, but his extension was added to the two years and $66.5 million that were still remaining on the six-year contract he signed in 2014. As a result, some view his new contract as a 12-year, $426.5 million pact. Even if the existing money isn’t included, Trout's $360 million extension was the richest deal in North American professional sports history at the time he signed.

, 3B, Padres: 10 years, $300 million (2019-28)

Machado set the record for the largest free-agent contract in sports history with his 10-year, $300 million deal -- which Harper broke just weeks later. Prior to Machado’s deal, the Padres had given out just one $100 million contract in franchise history -- $144 million to Eric Hosmer entering the 2018 season. The deal gave Machado the ability to opt out at the end of 2023, but the third baseman and the Padres agreed to an 11-year, $350 million extension that effectively replaced the six years remaining on his previous deal.

, 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. Stanton chose not to invoke the opt-out clause in his contract after the 2020 season, ensuring that he'll stay in pinstripes a while longer.

, 2B, Mariners: 10 years, $228.26 million (2014-23)

Canó was 31 at the start of his 10-year contract with the Mariners, and he’d already compiled 45.5 WAR (per Baseball Reference) over the course of a nine-year career to that point. Canó earned All-Star selections in three of his first four seasons with Seattle, but he was suspended for 80 games in 2018 after testing positive for a banned substance, and the club traded him to the Mets with closer Edwin Díaz for a five-player package that offseason. After another PED suspension cost Canó all of 2021, the Mets released him in 2022.

, 1B, Reds: 10 years, $225 million (2014-23)

Votto signed a 10-year extension just prior to Opening Day 2012, which kicked in for the 2014 season. Votto led the NL in OBP in three of the first seven years of the deal, and he had a resurgent season in 2021, producing 36 homers with a .938 OPS over 129 games. The Reds declined Votto's 2024 club option at the end of the 2023 season, making the first baseman a free agent for the first time.

, 1B, Angels: 10 years, $240 million (2012-21)

Pujols’ 11 years in St. Louis ended with him signing a 10-year deal with the Angels entering the 2012 season. Pujols had just finished a seven-year span where he’d hit .326 with a 1.037 OPS, 285 HR and won three National League MVP Awards. He received MVP votes in two of the first seven seasons with the Angels, but his production dwindled and he was released in 2021 before signing with the Dodgers. Pujols made a storybook return to the Cardinals in 2022 and went on to hit his 700th home run in September.

, 3B, Yankees: 10 years, $275 million (2008-17)

Rodriguez opted out of his 10-year, $252 million contract in October 2007, and two months later the Yankees re-signed him for 10 years and $275 million. At the time, it was the largest contract in MLB history, eclipsing his own record set with his previous contract. Rodriguez retired during the 2016 season, before the 10-year contract was up.

, SS, Yankees: 10 years, $189 million (2001-10)

After Jeter had been part of three straight World Series-winning teams and having won four in his career to that point, the Yankees gave him a 10-year extension entering the 2001 season. His best MVP finish came in 2006 when he finished second to Justin Morneau. He retired following the 2014 season and was elected to the Hall of Fame on his first ballot in 2020.

, SS, Rangers: 10 years, $252 million (2001-10)

Rodriguez’s first 10-year contract set the record for richest contract in MLB history, besting Mike Hampton's eight-year, $121 million contract signed earlier that offseason. Rodriguez hit .309 with a .934 OPS and 189 homers in the first seven years of his career, all with the Mariners. He was traded to the Yankees following the 2003 season and won two MVP Awards in New York (2005 and 2007), helping them win the 2009 World Series.

, OF, Yankees: 10 years, $23 million (1981-90)

At the time, Winfield’s contract with the Yankees was the richest in history. Winfield didn’t play out the entirety of the contract with the Yankees, missing the entire 1989 season with injury and eventually being traded to the Angels during the 1990 season. Winfield had finished third in MVP voting in 1979 with the Padres, but his best such finish with the Yankees was fourth in 1988.

Richie Zisk, OF, Rangers: 10 years, $2.75 million (1978-1987)

This was the first 10-year contract given to a position player, though he only spent three years in Texas before he was traded to Seattle following the 1980 season in an 11-player deal that included the infamous Mario Mendoza heading back to Texas. The Rangers signed Zisk for 10 years and $2.75 million. Zisk also did not play out the full length of his deal, and amassed a total of 6.7 WAR (per Baseball Reference) in his final seven seasons after signing it.

Wayne Garland, RHP, Guardians: 10 years, $2.3 million (1977-1986)

Garland was part of MLB's first free-agent class, but it wasn't the free agency you know today, as it was tied to a re-entry draft (more on that here). The most famous deal that offseason was Reggie Jackson's five-year, $3 million deal with the Yankees, but Garland's contract holds the distinction of being the first the 10-year contract given out by an MLB team. In 1976, he had a career year, going 20-7 with a 2.67 ERA for the Orioles and parlaying that into this historic deal. However, he appeared in just 99 games between 1977 and 1981, not even playing out the entirety of the contract due to a career-ending torn rotator cuff.