The Boston Red Sox’s winter will be crowded with harder choices, but the Garrett Whitlock decision is not one of them.
After the Yankees swept the Red Sox out of the Wild Card Series, the club is still looking for its first World Series since 2018, and chief baseball officer Craig Breslow has a roster that finally looks close enough to take the next step.
Most of the open questions involve free agents, a possible Sonny Gray retirement, and whether the front office can land a right-handed power bat.
The one item that already looks settled is the one-year, $8.25 million club option on Whitlock for 2027.
In his Red Sox 2026 offseason guide for Bleacher Report, Zachary D. Rymer called exercising that option a “no-brainer.”
Over the last two seasons Whitlock has appeared in 116 games and posted a 2.03 ERA across 124.1 innings, with a 2.15 FIP and a 4.55 strikeout-to-walk ratio.
Those are late-inning numbers at a price that would not buy a reliable setup man on the open market. Rymer noted that an injured-list stay for elbow inflammation this year still leaves a durability question, but not one large enough to change the math.
That math is even cleaner once the structure of the deal is considered. The option includes a $1 million buyout, so declining it would save only $7.25 million while sending a proven high-leverage arm into free agency.
Whitlock also carries a club option for 2028, which means Boston can keep the relationship alive another year if the right arm holds up.
For a team that just watched depth carry a 55-29 finish after a miserable start, and that did so largely without Garrett Crochet and Roman Anthony, locking in a reliever who has already shown he can absorb multi-inning work is the simplest piece of continuity available.
The bullpen picture around him is already taking shape. Aroldis Chapman triggered his one-year, $13 million vesting option by crossing 40 innings in August, so the late-inning lefty is returning after a 1.51 ERA since the start of 2024.
Whitlock gives Breslow a right-handed complement who has been equally dominant since returning from the elbow trouble that wiped out most of 2024. Together they form a back end that does not need to be rebuilt from scratch while the front office sorts through Patrick Sandoval, Isiah Kiner-Falefa, and the far larger Gray question.
Gray’s $30 million mutual option is the real drama. After an 18-5 season with a 2.72 ERA, he could retire if his family wants him home, or he could decline his side and chase more money in a thin free-agent class.
Either path leaves a hole near the top of the rotation. Whitlock does not fill that hole, but he does free Breslow to spend the winter on a starter or a left-field slugger instead of replacing a reliever who has already earned his keep.
In an offseason that will be judged on whether Boston finally gets past October, the $8.25 million call is the one move that should already be written in ink.
