Largest contract extensions in MLB history

February 26th, 2023

Landmark contract extensions have become a frequent occurrence in recent years.

Padres third baseman Manny Machado is set to become the latest star to reach a megadeal to stay with his club, as a source told's Mark Feinsand on Sunday that the 30-year-old was finalizing an 11-year, $350 million extension through 2033 with San Diego. Machado would have been able to opt out of his original Padres deal -- a 10-year, $300 million contract signed in free agency prior to the 2019 season -- at the end of 2023.

Machado will join a growing list of young players to reach blockbuster extensions, including Rafael Devers with the Red Sox, Wander Franco with the Rays, Fernando Tatis Jr. with the Padres, Francisco Lindor with the Mets, Mookie Betts with the Dodgers and Mike Trout with the Angels -- all deals that have happened since 2019.

Betts’ $365 million extension is the largest given to a player, in terms of new guaranteed total money added on to a player’s existing contract, while Tatis' 14-year extension is the longest by years.

Here's a look at the 12 largest contract extensions in Major League history, in descending order of total dollars. (For a list of the longest contracts -- including free agent deals -- click here.)

1) , Dodgers -- 12 years, $365 million
Signed in 2020, runs through 2032
The Red Sox traded Betts and southpaw David Price to the Dodgers in a blockbuster trade following the 2019 season, in large part because many expected the former American League MVP to test the market following the ‘20 campaign and challenge the recent free agency standards set by Bryce Harper and Manny Machado. But Los Angeles’ front office was able to hammer out a massive extension right as the shortened ‘20 season was set to begin, adding on to the record one-year, $27 million contract that Betts and the Red Sox agreed to in January '20 in order to avoid arbitration.

Making sure Betts stayed a Dodger was a no-brainer decision at the time, and proved even more so once the games got underway. Betts placed runner-up in the 2020 NL MVP Award vote, and then helped lead L.A. to a long-awaited World Series championship with a string of plays with his bat, legs and glove during the postseason.

2) , Angels -- 10 years, $360 million
Signed in 2019, runs through 2030
The Halos made sure the game’s consensus best player -- and one off to an historic start to his sure-to-be Hall of Fame career -- remained in Orange County for the foreseeable future. This deal added on to the two years and $66.5 million that were still remaining on the contract Trout signed in 2014, thus making his new 12-year, $426.5 million deal the richest in North American professional sports history at the time. Trout immediately rewarded the Angels’ faith in 2019 by bashing a career-high 45 home runs and winning his third career league MVP Award.

3) , Padres -- 11 years, $350 million (source)
Agreed to in 2023, runs through 2033
Machado originally joined the Padres on a 10-year, $300 million contract in February 2019, at the time setting a record for the largest free-agent deal in MLB history (though it has since been exceeded by several other deals). The contract gave him the ability to opt out at the end of the 2023 season, and Machado told reporters during Spring Training that he planned to exercise his opt-out power to test the open market. However, it appears he’ll be staying in a Padres uniform for years to come. The extension will begin in 2023, effectively replacing the six years left on his previous deal with a new 11-year contract running through 2033.

4) , Mets -- 10 years, $341 million
Signed in 2021, runs through 2031
Under new owner Steve Cohen, the Mets hinted that the 2020-21 offseason would be a big one in Queens, and they delivered, landing Lindor and right-hander Carlos Carrasco in a trade with Cleveland. Once that deal was done, speculation turned to whether the Mets would be able sign Lindor, a four-time All-Star and two-time Gold Glove Award winner, to a long-term extension. The two sides reached a deal on March 31, the eve of Opening Day. Lindor's 2021 salary of $22.3 million remained unchanged, and the extension -- the richest ever for a shortstop -- took effect in '22.

5) , Padres -- 14 years, $340 million
Signed in 2021, runs through 2034
After a promising but abbreviated rookie year in 2019, Tatis consolidated his promise with an electric performance in the pandemic-shortened '20 campaign, slashing .277/.366/.571 with 17 homers in 224 at-bats and placing fourth in the NL MVP Award vote. His play was a major reason why the Padres snapped a 14-year postseason drought, and then he thrived under the brighter lights by becoming the third-youngest player to hit multiple homers in a playoff game. While the Padres missed the playoffs in 2021, Tatis finished with an NL-leading 42 homers, plus 25 steals and a .975 OPS in 130 games. However, he missed the '22 season with a wrist injury, followed by a suspension for a banned substance.

6) Rafael Devers, Red Sox -- 11 years, $331 million
Signed in 2023, runs through 2033
With Xander Bogaerts departing for the Padres in free agency after the 2022 season, the Red Sox put their attention on keeping their other superstar, Devers, in Boston for the long haul. A year before Devers would have reached free agency, the Red Sox reached an agreement with their two-time All-Star third baseman on the largest contract in franchise history. Devers' deal surpasses the seven-year, $217 million free-agent contract David Price signed with the Red Sox in 2016, and the seven-year, $154 million extension Adrián González signed with them in 2011.

7) , Marlins -- 13 years, $325 million
Signed in 2014, runs through 2028
Baseball had not seen this type of contract -- both in terms of length and total value -- before Stanton put ink to paper following the 2014 season. But the hulking slugger is playing out the majority of this deal with the Yankees, and not the Marlins; Stanton logged the first three seasons of the contract with Miami before the club traded him to New York in December '17, shortly after he won that year’s NL MVP Award. Stanton didn't enact his opt-out clause after the '20 season, choosing to stay in the Bronx after some injury-plagued seasons in pinstripes.

8) , Tigers -- 8 years, $248 million
Signed in 2014, runs through 2023
History repeated itself a bit here, as Dave Dombrowski -- the same general manager who signed Miggy to an eight-year, $152.3 million extension shortly after acquiring Cabrera for the Tigers via a trade in 2007 -- made sure Cabrera would stay in Detroit with an even bigger eight-year extension. This extension added on to the remaining two years and $44 million from Cabrera’s previous deal, and briefly positioned the slugger for the highest annual average value in history at $31 million. Cabrera certainly earned a massive extension as he was coming off back-to-back AL MVP awards (including a Triple Crown season in 2012), but injuries have taken their toll in the latter half of this deal. He plans to retire after his contract runs out at the end of 2023.

9) , Rockies -- 7 years, $235 million
(One year, $15 million later added onto deal)

Signed in 2019, runs through 2027
Less than one month after Arenado agreed to a then-record one-year, $26 million contract with Colorado to avoid arbitration, he was able to hammer out an extension with the club, adding seven years and $235 million to his existing contract. When the Rockies traded Arenado to the Cardinals prior to '21 in exchange for left-hander Austin Gomber and four Minor League players, St. Louis tacked another year for $15 million onto the end of the contract in exchange for Arenado agreeing to waive his no-trade clause. He also gained the ability to opt out of his deal after the 2022 season, although he later chose not to do so.

10) , Reds -- 10 years, $225 million
Signed in 2012, runs through 2023
Votto won the 2010 NL MVP Award and the Reds signed a three-year deal after that season in order to avoid arbitration. But eventually, Cincinnati rewarded its superstar in grand fashion. Votto has paced the Senior Circuit in his specialty, on-base percentage, five more times since signing this extension. After a subpar season in 2022, Votto likely will need a significant rebound for the Reds to exercise their $20 million club option for '24.

11) , Dodgers -- 7 years, $215 million
Signed in 2014, signed additional extension in 2018
The reasons to give Kershaw a massive extension didn’t require too much analysis. The southpaw had already captured two NL Cy Young Awards through his age-25 season and finished runner-up in another campaign, and he had lowered his career ERA in each successive season since making his debut -- a trend that would continue all the way through 2017. The Dodgers looked really smart immediately after Kershaw signed in January ‘14, as he went on to win both his third Cy Young and the NL MVP Award after going 21-3 with a 1.77 ERA and 239 strikeouts. He and L.A. finally captured their long-awaited World Series championship in '20. Kershaw has since become a free agent twice but re-signed both times.

12) , Yankees -- 10 years, $189 million
Signed in 2001, ran through 2010
This was the culmination of a prolonged negotiation process between Jeter and the Yankees that spanned 13 months. At the time, it trailed only the $252 million contract that Alex Rodriguez -- Jeter’s future teammate -- signed with the Rangers in terms of the richest contract in baseball history. After signing in February, Jeter helped lead the Yankees to their fourth straight World Series appearance (earning his Mr. November moniker that fall) and continued his run as one of the most beloved players in Yankees history for the rest of the decade and beyond. He was elected to the Hall of Fame with 99.7% of the Baseball Writers' Association of America vote in 2020.