Keep or Cut Ties? Early Returns on 5 Red Sox Contracts to Watch in 2026

It's no secret that the 2026 Major League Baseball season has been a struggle so far for the Boston Red Sox.

We're 35 games into the 2026 season and the Red Sox currently are 14-21 on the season and in last place in the American League East and have already fired former manager Alex Cora. If you had said this past offseason that the Red Sox would be among the worst teams in baseball just over 20 percent of the way through the season, you would've shocked some people. But, alas, here we are.

There's still enough time to turn things around and Boston is 4-4 since firing Cora. But the club needs a lot to go right. While there's a lot of season left to go, here's a look at five contract situations for the Red Sox to watch throughout the season with an eye towards the future.

Sonny Gray — Mutual Option For 2027

Apr 14, 2026; Minneapolis, Minnesota, USA; Boston Red Sox starting pitcher Sonny Gray (54) delivers a pitch against the Minnesota Twins in the first inning at Target Field. Mandatory Credit: Jesse Johnson-Imagn Images | Jesse Johnson-Imagn Images

Gray is currently on the Injured List for Boston, but should be back in the very near future. He has made five starts so far this season and has a 4.30 ERA. Gray is 36 years old and has a $30 million mutual option for the 2027 season with a $5 million buyout. Mutual options are rarely picked up. Unless these two sides agree to a renegotiated deal, a trip to free agency is very likely.

Patrick Sandoval — Unrestricted Free Agent After 2026

Boston Red Sox Left-handed pitcher Patrick Sandoval — Left-handed pitcher Patrick Sandoval makes his first rehab start with Triple-A Worcester on April 8, 2026, after undergoing surgery on his left elbow in 2024. | Ashley Green/WooSox Photo / USA TODAY NETWORK via Imagn Images

Sandoval is going to be a free agent after the season after inking a two-year deal worth just over $18 million before the 2025 season. Unfortunately, this deal has been a whiff for Boston. Sandoval hasn't pitched in a game for the organization and is on the 60-Day Injured List.

Isiah Kiner-Falefa — Unrestricted Free Agent After 2026

Apr 14, 2026; Minneapolis, Minnesota, USA; Boston Red Sox second baseman Isiah Kiner-Falefa (2) throws the ball to first base for an out against the Minnesota Twins in the fourth inning at Target Field. Mandatory Credit: Jesse Johnson-Imagn Images | Jesse Johnson-Imagn Images

Kiner-Falefa inked a one-year, $6 million deal with Boston and is slashing .229/.270/.229 with zero homers and three RBIs in 16 games played. He can play all over the infield, but it would be a bit surprising to see a new deal for the 2027 season.

Garrett Whitlock — Club Option For 2027

May 3, 2026; Boston, Massachusetts, USA; Boston Red Sox relief pitcher Garrett Whitlock (22) pitches against the Houston Astros during the seventh inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

A true no-brainer. Whitlock has a club option worth just over $8 million for the 2027 season. That's an obvious one. He's one of the best setup men in baseball. It would be a shock if the option wasn't picked up.

Danny Coulombe — Unrestricted Free Agent After 2026

Apr 20, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Danny Coulombe (67) pitches during the fourth inning against the Detroit Tigers at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images | Bob DeChiara-Imagn Images

Coulombe inked a one-year deal worth just over $1 million. He'll be a free agent after the season and has a 5.63 ERA through 12 appearances so far in Boston. He's hurt right now, but when he returns, he'll have plenty of time to get that ERA down. At a similar price point, it wouldn't hurt to bring him back in 2027.

Add us as a preferred source on Google