Largest Contract Extensions In MLB History (www.mlb.com)

Another year, another landmark contract extension.

Budding superstar Fernando Tatis Jr. and the Padres sent shockwaves through the baseball world as pitchers and catchers reported to Spring Training on Wednesday, reportedly agreeing to a

that kicks off in 2021. This is the third straight year that an extension has made major headlines, following Mookie Betts’ 12-year extension with the Dodgers last spring and Mike Trout’s 10-year extension with the Angels in ’19. Both Betts and Trout were set to become free agents after the ’20 campaign, giving each of them leverage to command massive deals. The Padres, meanwhile, decided they needed to ensure their 22-year-old talent, Tatis, remained in San Diego for a long, long time.

Betts’ extension is the largest given to a player, in terms of new total money added on to a player’s existing contract, while Tatis’ extension is the longest by years. Here is a look at the 10 largest extensions in Major League history, in descending order of total dollars.

1) Mookie Betts, 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) Mike Trout, 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 leading the American League in OBP, slugging and OPS to earn his third career league MVP Award.

3) Fernando Tatis Jr., Padres — 14 years, $340 million (source)
Agreed to 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. Tatis’ 39 career home runs through ’20 were already the most by any primary shortstop within his first 150 career games dating back to 1900, and he had only logged 143 games to that point. Now, Tatis is the face of the Padres’ franchise turnaround as they get set to battle Betts and the Dodgers for NL West supremacy.

4) Giancarlo Stanton, 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 chose not to enact his opt-out clause after the ’20 season, meaning he’ll stay in the Bronx after some injury-plagued seasons in pinstripes.

5) Miguel Cabrera, 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 sapped him of playing time in the latter half of this deal.

6) Nolan Arenado, Rockies — 7 years, $234 million
Signed in 2019, runs through 2026
Arenado had agreed to a then-record one-year, $26 million contract with Colorado to avoid arbitration, but he was then able to hammer out an extension with the club less than one month later. The extension added on to that one-year deal, giving Arenado a combined $260 million through 2026. Arenado will not finish out this deal in Colorado, however; the Rockies decided to trade him to the Cardinals prior to ’21 in exchange for left-hander Austin Gomber and four Minor League players.

7) Joey Votto, 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.

8) Clayton Kershaw, 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.

9) Derek Jeter, 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.

10) Christian Yelich, Brewers — 7 years, $188.5 million
Signed in 2020, runs through 2028
The Brewers made their new face of the franchise a $200 million man once they added this extension to the two years and $28.5 million remaining on Yelich’s previous deal. After arriving in Milwaukee from Miami via trade, Yelich immediately evolved into one of the game’s best players. He exploded in the second half of the 2018 season, finishing just shy of the NL Triple Crown while batting .326 with 36 homers to win the NL MVP Award, and then was even better in ‘19 before a late-season knee injury led to a runner-up finish behind eventual league MVP Cody Bellinger. That was plenty enough to convince the Brewers to keep Yelich in Milwaukee long-term.

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