Sonny Gray Will Force Red Sox Into Difficult Trade Deadline Decision

It's so easy to foresee...

May 18, 2026; Kansas City, Missouri, USA; Boston Red Sox starting pitcher Sonny Gray (54) delivers a pitch against the Kansas City Royals during the first inning at Kauffman Stadium. Mandatory Credit: Denny Medley-Imagn Images | Denny Medley-Imagn Images

Sonny Gray was supposed to be a surefire playoff starter for the Boston Red Sox this year. Now, he's putting the team in a pickle.

At long last, the Red Sox recorded their 20th win of the season on Monday, and it was Gray's brilliance that got them there. Though they could only muster three runs of offense (a mark they haven't surpassed for the last nine games), they got six-plus innings of one-run, nine-strikeout ball from the three-time All-Star.

The Red Sox are 20-27. That abysmal start has them squarely in limbo when it comes to the trade deadline, which is admittedly still over two months away. But we've seen enough of a sample already to project that this front office, led by the ever-polarizing Craig Breslow, will have a brutally complicated decision to make at the end of July.

If you like our content, choose Sports Illustrated as a preferred source on Google.

Why Gray trade decision will be so tough

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

Even after a three-week stint on the injured list, Gray has settled into a nice rhythm with the Red Sox. He set his new season-high in punchouts on Monday, most of which came on his devastating sweeper. He lowered his ERA to 2.93 in 40 innings, now with 30 strikeouts to boot.

If Boston could guarantee it would be comfortably in the playoff hunt by the deadline, there would be no debate here. If it was obvious that the playoffs weren't in the cards, however, it would be a no-brainer to start a bidding war for Gray and load up on prospects.

But with how weak the American League is this season, the Red Sox are almost certainly going to be a few games out of the wild card race, yet still be underachieving based on preseason expectations. That middle ground is a special kind of hell, and the Red Sox have been in it far too often this decade.

The Red Sox's obligations to Gray were $21 million after the cash considerations from the Cardinals were factored into the trade, so by the end of July, a team would only owe him about $7 million for the rest of the season. No team would object to that added cost if it meant they could add a viable playoff starter.

Escaping the middle ground would be ideal, but it's far too easy to predict that won't happen. The Red Sox are going to have a very tricky, very important call to make on Gray in a couple of months.