The largest contract extension in MLB history

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With the Boston Red Sox and Rafael Devers agreeing to long-term contract terms, let’s take a look at the largest contract extension in MLB history.

The Boston Red Sox didn’t make their fanbase happy with the moves they made in the offseason, especially after they watched Zander Bogaerts sign an 11-year, $280 million contract with the San Diego Padres. That left the fandom calling for the team to re-sign third baseman Rafael Devers. And they did just that.

A day after the team and Devers avoided arbitration before the 2023 season, the two sides agreed to terms of an 11-year, $331 million contract extension. With this, the Red Sox managed to avert disaster and ensure that the best player on the roster was not going anywhere.

While an 11-year, $331 million contract extension is huge, does it rank near the top as one of the largest contract extensions of all time?

The largest contract extension in MLB history

Let’s take a look at the 10 biggest contract extensions in league history, Courtesy of MLB.com:

  1. Mookie Betts: 12 years, $365 million, with the Los Angeles Dodgers
  2. Mike Trout: 10 years, $360 million, with the Los Angeles Angels
  3. Francisco Lindor: 10 years, $341 million, with the New York Mets
  4. Fernando Tatis Jr.: 14 years, $340 million with the San Diego Padres
  5. Rafael Devers: 11 years, $331 million, Boston Red Sox
  6. Giancarlo Stanton: 13 years, $325 million, with the Miami Marlins
  7. Miguel Cabrera: 8 years, $248 million, with the Detroit Tigers
  8. Nolan Arenado: 7 years, $235 million, with the Colorado Rockies
  9. Joey Photo: 10 years, $225 million, with the Cincinnati Reds
  10. Clayton Kershaw: 7 years, $215 million, with the Los Angeles Dodgers

Ironically, the most lucrative contract extension belongs to Mookie Betts, the former Red Sox star outfielder. Prior to the 2020 season, the Red Sox and Betts were unable to reach an agreement, as the team traded him to the Dodgers. Shortly thereafter, the Bates and Dodgers came to an agreement on a 12-year, $365 million deal.

Mike Trout has the second most lucrative deal after agreeing to a 10-year, $360 million deal with the Angels.

Places #3 and #4 belong to Francesco Lindor and Fernando Tatis Jr., both $1 million apart. Of course, Tatesse got four more years on his deal.

Devers officially has the fifth largest contract extension in MLB history.

We’ll see if any player and team can make this list. Perhaps most importantly, who can break the record set by the Bates and Dodgers?

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