Craig Breslow didn’t flinch on Garrett Whitlock’s $8.25 million option. Boston exercised the 2027 club option a day after the calendar flipped to November, locking in a setup man who posted a 1.72 ERA across 54 appearances in 2026, striking out 59 against just nine walks in 52⅓ innings in front of closer Aroldis Chapman. That’s the easiest transaction decision the front office will make all winter.
The #RedSox today exercised RHP Garrett Whitlock’s 2027 club option.
— Red Sox (@RedSox) November 1, 2026
It’s also the smallest one. Sonny Gray, the only starter in the rotation who pitched like a true No. 2 all season, is now a free agent after both sides declined his $30 million mutual option, with Gray taking a $10 million buyout on the way out. Gray gave Boston a 2.72 ERA and a 1.15 WHIP across 29 starts, held opponents to a .236 average, and won 18 games doing it. Replacing that production is an entirely different problem than picking up a bargain option on a reliever who was already going to say yes.
Garrett Crochet is the only proven arm left behind him, and he spent stretches of 2026 banged up. A health scare for your ace is supposed to be the argument for adding rotation depth the following winter, not a footnote to skip past. Miss even a handful of Crochet’s starts again and Boston is down to one reliable arm. The team needs someone who can take the ball 28 to 30 times without drifting too far from Gray’s numbers. Nobody on the current roster fits that description.
Gray’s gone now anyway. Boston just spent $10 million for the privilege of watching him walk instead of trading him in July for even one young arm. This site argued back then that the deadline was the moment to move him. Nobody in Boston’s front office was listening, and the return this time is a buyout check instead of a prospect.
The lineup has its own version of the same gap. Boston hit 163 home runs in 2026, fifth-fewest in the league, with only two hitters clearing 24: Willson Contreras at 27 and Wilyer Abreu at 24. Almost every other spot in the order comes up empty on power. One deadline slugger won’t fix a gap that wide, and it’s been sitting there since spring. Contreras isn’t quiet about it. He called out what Breslow needs to do once the season ended.
Willson Contreras on the Red Sox offseason:
“I think we need some more offense. That’s for Breslow to figure out.”
(via @PeteAbe) pic.twitter.com/RAQbgVjsPR
— Gordo (@BOSSportsGordo) October 31, 2026
Breslow is the one holding that assignment now, and he knows it. Jarren Duran’s name belongs in the same conversation. Chris Cotillo has him squarely in trade play this winter; there’s some signal he’d welcome it, but none of it is close to finished business.
Whitlock getting done fast doesn’t make any of this easier. Boston solved the one problem that was never really a problem. The No. 2 starter and the right-handed bat are the actual test of this offseason, and as of today, Breslow hasn’t produced a single name for either one.
