The longest contracts in baseball history

January 10th, 2023

When Fernando Tatis Jr. signed a 14-year extension worth $340 million with the Padres in 2021, it set a new standard for the longest pact in MLB history.

There have now been 22 MLB contracts totaling 10 years or longer after a 2022 offseason in which Rafael Devers reportedly agreed to an 11-year, $331 million contract extension with the Red Sox, Trea Turner reached an 11-year, $300 million deal with the Phillies and Xander Bogaerts joined the Padres for $280 million over 11 years.

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

, 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 extension with the Angels 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.

, 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 '20 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.

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

With his former teammate Bogaerts leaving Boston on a different 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 is finalizing would be an even larger contract than the $280 million deal Bogaerts inked with the Padres. Devers' would be the fifth-largest extension in MLB history by total dollars and a franchise-record contract for the Red Sox.

, 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 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.

Less than 24 hours after reportedly missing out on the biggest free agent of them all, Aaron Judge, who reached reported nine-year, $360 million deal to remain with the Yankees, the Padres continued to flex their financial muscle and continued to show they are serious about competing with the Dodgers for supremacy in the NL West just a few months after trading for superstar right fielder Juan Soto.

, 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 reunites 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. Now, he'll aim to help Philadelphia get over the hump after the Phils lost to the Astros in the 2022 Fall Classic.

, 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 ‘20 campaign and challenge the standards set by Harper, Trout and Machado. But Los Angeles’ front office was able to hammer out a massive extension right as the shortened ‘20 season began, adding on to the record one-year, $27 million contract that Betts and the Red Sox agreed to in January of '20 in order to avoid arbitration. Betts’ extension marked the most money given out by the Dodgers in a single contract, surpassing the $215 million extension that Clayton Kershaw signed in '14. Betts' addition paid immediate dividends. He was instrumental in leading Los Angeles to the '20 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. He has slugged .556 and clubbed 83 homers across his first three years with the Phillies, though the club is still looking to return to the postseason. 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).

, 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.

, 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 '14. 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.

, 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 '20 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. Votto will be 39 years old for the majority of the final year of the contract (he’ll turn 40 in September of that year).

, 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 '88.

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 '77 and '81, not even playing out the entirety of the contract due to a career-ending torn rotator cuff.