As free agency gets underway, the Boston Red Sox have many holes to fill to be competitive in 2025.
Although the front office has been frugal lately, that hasn't always been the status quo in Boston. The Red Sox used to be a lock as serious contenders for the league's biggest free agents, and often signed them.
Here's a look at the biggest free agent contracts the Red Sox have ever handed out. Hopefully, this list will look different come Opening Day.
Here are the 5 largest free agent contracts in Red Sox history
5. J.D. Martinez (five years, $110 million)
Martinez first hit free agency after an otherworldly 62-game stint with the Arizona Diamondbacks in 2017, during which he hit 29 homers and slugged .741. His performance earned him a large payday and high expectations in Boston, and it's safe to say he exceeded those expectations.
During his time with the Sox, Martinez batted .292/.363/.526, and his only real off-year was the pandemic-shortened 2020 season. His 2018 campaign was particularly memorable, as he led all of MLB with 130 RBIs and 358 total bases, finishing fourth in AL MVP voting as the Red Sox won their ninth World Series in franchise history.
4. Trevor Story (six years, $140 million)
If Martinez's stint in Boston was a daydream, Story's has been a nightmare. After an amazing start to his career in Colorado, Story cashed in after hitting free agency, securing over $23 million a year from the Red Sox to be their new second baseman. However, in the first three years of his six-year deal, Story has been unable to stay healthy, and he's played just 163 games as a result. Moreover, even when he has been healthy, he hasn't been effective, with just a .693 OPS in Boston. If the Red Sox can find a way out of any portion of this contract, they will.
3. Carl Crawford (seven years, $142 million)
This is another contract that the Red Sox would like back. During his nine seasons in Tampa Bay, Crawford established himself as an elite baserunner and contact hitter. He stole over 50 bases in five of those nine seasons and had a career .296 average.
Things didn't go quite so well in Boston, as Crawford managed just a .694 OPS and only stole 18 bases in 130 games in 2011 as the Sox collapsed in September to miss the playoffs. He missed nearly all of 2012 with an injury and was traded to the Dodgers after the year. There's no love lost between Crawford and the city of Boston, as he once claimed the Boston sports media loved when athletes were miserable.
2. Manny Ramírez (eight years, $160 million)
This contract is the definition of money well spent. Already an established superstar in Cleveland, Ramírez signed with the Red Sox after the 2000 season. Not only did Ramírez slash .312/.411/.588 in seven and a half years with Boston, but he was also an animal in the postseason. He helped the Red Sox break the Curse of the Bambino in 2004 and won World Series MVP in the process. His .999 OPS with the Red Sox remains the third-best in franchise history.
1. David Price (seven years, $217 million)
David Price threw 7-plus innings of one-run ball in a dominant World Series performance #TipOfTheCap pic.twitter.com/DVk1wn9k4f
— Red Sox (@RedSox) October 29, 2018
Price's tenure in Boston was...interesting. After he signed his mammoth contract, Price pitched fairly well when healthy in the first three seasons. He made the front office look good when he threw 13.2 innings with a 1.98 ERA in the 2018 World Series. Unfortunately, he struggled in 2019, missing time with nagging injuries.
The Red Sox were eager to dump payroll in 2019 and included Price in the infamous Mookie Betts trade, shipping him off to LA. Price wasn't necessarily bad in Boston, but he might not have been worth $31 million a year.