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The 7 biggest contracts and extensions in Boston Red Sox history

By Gabrielle Starr

LOS ANGELES, CA - OCTOBER 28: David Price #24 of the Boston Red Sox celebrates with the World Series trophy after his team's 5-1 win over the Los Angeles Dodgers in Game Five to win the 2018 World Series at Dodger Stadium on October 28, 2018 in Los Angeles, California. (Photo by Harry How/Getty Images)
LOS ANGELES, CA - OCTOBER 28: David Price #24 of the Boston Red Sox celebrates with the World Series trophy after his team's 5-1 win over the Los Angeles Dodgers in Game Five to win the 2018 World Series at Dodger Stadium on October 28, 2018 in Los Angeles, California. (Photo by Harry How/Getty Images) /
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Will the Red Sox give Rafael Devers the biggest contract in franchise history?

Will Rafael Devers become the Boston Red Sox’ first $300 million man?

To date, only eight players – none of them Sox – have signed contracts totaling $300M or more: Mike Trout, Mookie Betts, Francisco Lindor, Fernando Tatis Jr., Bryce Harper, Giancarlo Stanton, Corey Seager, Gerrit Cole, and Manny Machado. Juan Soto also rejected a $440M offer from the Washington Nationals this summer, which led to them trading him to the San Diego Padres.

The Sox have spent over the luxury tax threshold so often times in recent years and have overspent on so many players that it’s hard to believe only one has received a contract in excess of $200M yet. After over a year of lowballing him, the Sox eventually made Betts a $300M offer, but he turned it down and signed an even bigger deal when they traded him to the Dodgers ahead of the 2020 season.

So, who are the seven players who received the biggest free-agent contracts and extensions in franchise history? Keep in mind, this isn’t a list of Boston’s biggest earners; David Ortiz is one of them over his entire Red Sox career, but the only long-term deal they gave him was the four-year, $52M extension in 2005. Several players on this list didn’t even last two full seasons and rarely have the Sox ended up paying full price, but here’s who they agreed to pay the most:

1. David Price – 7 years, $217M

When the Red Sox gave David Price a 7-year, $217M contract in 2015, it not only topped their own franchise record by a wide margin, it also made him the highest-paid pitcher in MLB history.

Unfortunately, it turned out to be an exorbitant overspend, as is often the case with big contracts. Price dealt with injuries and general underperforming during his Boston tenure. He was able to redeem himself in a big way during the 2018 ALCS and World Series, but does that make the entire contract worth it?

The Sox ended up paying the Dodgers to take Price off their hands, bundling him with Betts in one of the most unbalanced trades since some foolish team decided they didn’t need Babe Ruth a hundred years ago. The Dodgers absorbed $64M of the remaining three years on Price’s deal, so the Sox ended up paying him a grand total of $153M, including $16M in 2022.

As of November 2022, Price’s contract is the 19th most lucrative in baseball history, but Gerrit Cole ($324M) and Stephen Strasburg ($245M) are the only pitchers to surpass him thus far.

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