Largest contract extensions in MLB history

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

The Boston Red Sox have not exactly made their fanbase happy with the moves they made in the offseason, especially after they watched shortstop Xander Bogaerts sign an 11-year, $280 million contract with the San Diego Padres. That left the fanbase calling on the team to re-sign third baseman Rafael Devers. And they did exactly that.

One day after the team and Devers avoided arbitration ahead of the 2023 season, the two sides agreed to terms on an 11-year, $331 million contract extension. With this, the Red Sox were able to avoid disaster and ensure their best player on the roster is going nowhere.

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?

Largest contract extensions in MLB history

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

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

Ironically, the most lucrative contract extension belongs to Mookie Betts, the former Red Sox superstar outfielder. Ahead of the 2020 season, the Red Sox and Betts couldn’t reach an agreement, where the team traded him to the Dodgers. Shortly afterward, Betts and the Dodgers reached an agreement on the 12-year, $365 million deal.

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

The No. 3 and 4 spots belong to shortstops Francisco Lindor and Fernando Tatis Jr, both of whom are separated by $1 million. Of course, Tatis received four more years on his deal.

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

We shall see if any player and team will be able to make this list. Perhaps most importantly, who can break the record set by Betts and the Dodgers?