3 Red Sox Players With Interesting Contract Options to Monitor This Season

There are going to be some contract decisions to make for the Boston Red Sox.

Oct 1, 2025; Bronx, New York, USA; Boston Red Sox relief pitcher Garrett Whitlock (22) reacts during the eighth inning of game two of the Wildcard round of the 2025 MLB playoffs against the New York Yankees at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

It's very early to be thinking about contracts and other things of that nature for the Boston Red Sox, but it doesn't hurt to look ahead.

Last year, one interesting contract quirk to follow all season was Lucas Giolito. It was known that if Giolito pitched under 140 innings, then there would have been a $14 million club option for the 2026 season. If he went above 140 innings, then that option turned into a $19 million mutual option. Giolito finished the season with 145 innings pitched, which unlocked the $19 million mutual option, which was declined. If he had gone just under 140 innings, who knows what would've happened?

Now, Giolito is somehow still a free agent despite a good season with Boston in 2025. That just goes to show the importance of these contract talks. If he didn't reach 140 innings, would $14 million have been low enough for Boston to keep him? There's no way to know.

So, what about 2026? He are three contract situations to follow during the season.

Garrett Whitlock

Mar 17, 2026; Miami, FL, United States; United States pitcher Garrett Whitlock (59) throws pitch against Venezuela in the ninth inning during the 2026 World Baseball Classic Championship game at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images | Sam Navarro-Imagn Images

For Whitlock, it should be fairly straightforward. The Red Sox have a club option for Whitlock for the 2027 season worth $8.25 million. There's a $1 million buyout if the Red Sox were to turn it down. It would be a pretty big shock if Boston turned it down. But, again, it's early in the season so this is something to watch, at least.

Aroldis Chapman

Boston Red Sox pitcher Aroldis Chapman (44) reacts after a pitch is called a ball in the ninth inning of the MLB Opening Day game between the Cincinnati Reds and the Boston Red Sox at Great American Ball Park in downtown Cincinnati on Thursday, March 26, 2026. The Reds lost the season opener, 3-0. | Sam Greene/The Enquirer / USA TODAY NETWORK via Imagn Images

Chapman has been a revelation for Boston. He won the closer job in Spring Training in 2025 and then went on to win the Mariano Rivera American League Reliever of the Year Award in 2025. Chapman signed a one-year deal for the 2026 season worth $13 million with a vesting option for 2027. The option becomes guaranteed with 40-plus innings pitched in 2026 and a passed physical.

Sonny Gray

Mar 28, 2026; Cincinnati, Ohio, USA; Boston Red Sox pitcher Sonny Gray (54) throws against the Cincinnati Reds in the second inning at Great American Ball Park. Mandatory Credit: Aaron Doster-Imagn Images | Aaron Doster-Imagn Images

Gray's contract is the most complicated. Right now, it's a $30 million mutual option for the 2027 season. With Gray coming to Boston, his deal got altered and right now, per Spotrac, there's a $10 million buyout on his deal for 2027. Gray is 36 years old. It's hard to believe that the Red Sox are going to pick up their end of the bargain and pay Gray $30 million in 2027. But that $10 million also comes into play. For the 2026 season, he's going to be great in the long run. Beyond the 2027 season, there are certainly question marks with this deal right now.