Longest contracts in baseball history

February 18th, 2021

The Padres have reportedly made sure that Fernando Tatis Jr. will stay in San Diego for, essentially, the rest of his career. Tatis has agreed to a 14-year extension worth $340 million, a source told MLB.com's Mark Feinsand, the longest pact in MLB history.

Tatis' extension follows previous mega-deals signed by fellow superstars Mookie Betts, Bryce Harper, Mike Trout and Manny Machado in recent years. It's the 15th contract of at least 10 years in MLB history, including extensions where at least 10 years were added to the existing deal. Here's a look at all of them, in reverse chronological order of the year each contract will run through. While many of these will be familiar to you, it's safe to say there are a couple of which you may not be aware.

, SS, Padres: 14 years, $340 million (2021-2034)

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 contained 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.

, OF, Dodgers: 12 years, $365 million (2021-2032)

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.

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

Harper’s contract was tied for the longest in MLB history before Tatis' reported extension, and it’s the most money and years given to any free agent in North American professional sports history. He has slugged .518 and clubbed 48 homers across his first two 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).

, 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.

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, 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. He’d already compiled 45.5 WAR (per Baseball Reference) over the course of a nine-year career to that point. He has three years remaining on his contract and is now with the Mets after a trade during the winter in '18. He will sit out the '21 campaign while serving a season-long suspension for testing positive for a banned substance. Canó will be 40 in the final season of the contract.

, 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 played in just 62 games in the first season of that extension as a result of a left quad injury, but he’s played in 142 or more games in each full season since, and he led the NL in OBP in three of the first seven years of the deal. 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 has seen his power numbers dwindle -- in the shortened 2020 season, he hit .224/.270/.395 with six home runs, including his 661st career homer to surpass Willie Mays for fifth on the all-time list.

, 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, Indians: 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.