Even the most fervent of Chief Baseball Officer Craig Breslow critics can not deny his willingness to act both boldly and decisively.
His first move after getting hired as the Boston Red Sox Chief Baseball Officer was to trade starting outfielder Alex Verdugo to the archrival New York Yankees, marking just the third major-league trade between the two clubs since 1997. Breslow’s second offseason was defined by his trade for Chicago White Sox ace Garrett Crochet, a deal made possible by the staggering prospect package they surrendered that topped all other competitors. And while the jury is very much out (to put it kindly) on Rafael Devers, there is no question that it took serious guts to trade the face of the franchise in the middle of June.
With all this in mind, it should come as no surprise that Breslow and the Red Sox became the first team to strike this Hot Stove season with their acquisition of St. Louis Cardinals right-hander Sonny Gray on Tuesday. The 35-year-old Gray had found the fountain of youth after a tumultuous mid-career foray to New York and Cincinnati, pitching to a superb 3.53 ERA and 3.16 FIP over his last four campaigns.
Sonny Gray Offers Reliability to Red Sox
Compared to Breslow’s previous two veteran starting pitcher acquisitions, Lucas Giolto and Walker Buehler, both of whom arrived in Boston after career-worst campaigns and carried serious concerns, Gray is as dependable as they come. Along with Tarik Skubal, Gray is one of only two pitchers to pitch at least 150 innings and walk fewer than 40 batters in each of the last three seasons. And unlike many other pitchers with impeccable control, Gray also generates an elite number of whiffs, as he is one of only five arms to strike out at least 200 batters in each of the last two seasons.
While some fans may be squeamish at Gray’s 4.23 ERA, that figure is at least partly the result of a .329 BABIP that was over 40 points higher than his career average. Given that Gray actually posted a lower average exit velocity than his 2023 Cy Young runner-up campaign, it can be expected that Gray’s ERA will more closely align with his 3.39 FIP if he receives his normal level of batted-ball luck.
Adding to the appeal of Gray was the modest cost it took to acquire his services. With new President of Baseball Operations (and ex-Red Sox executive) Chaim Bloom taking over after this past season, the Cardinals were eager to get Gray’s $41 million salary off the books as they prepare for a potential lengthy rebuild. They were so eager, in fact, that they agreed to pay $20 million of Gray’s 2026 contract. This means that instead of paying Gray more than any other starting pitcher besides Zach Wheeler, the Red Sox will be on the books for a sum less than the qualifying offer.
Though this currently represents the third-highest salary on the club behind Trevor Story and Garrett Crochet, it is a completely tolerable amount if Gray is anywhere near the pitcher he has been this decade.
Red Sox Won't Lose Sleep Over Trade Price with Cardinals
Of course, part of the reason the Cardinals were willing to take on the salary was to receive a better prospect package, but while Richard Fitts and Brandon Clarke are interesting enough arms, they are not pitchers the Red Sox will lose sleep over. The soon-to-be 26-year-old Fitts had every opportunity to break into the Red Sox’s injury-plagued injury, but he himself missed time with a pec strain and elbow tendonitis. When he was able to take the mound, he looked the part of an unspacular fifth starter, posting averageish walk and strikeout rates but allowing far too much hard contact. Given his age and the lack of a standout pitch, there doesn’t appear to be much room for growth, and he would have had a hard time breaking into a suddenly crowded Red Sox rotation.
Clarke, on the other hand, is nearly the polar opposite of Fitts. The 2024 fifth-round pick has electric stuff, including a fastball that sits in the upper-90s and a slider that received a 70 grade from MLB Pipeline on the 20-80 scale, but he carries serious reliever risk due to durability and command concerns. The lanky lefty underwent Tommy John surgery in college and was limited to just 38 innings due to a blister injury in 2025. And though he struck out 60 batters in those 38 innings, Clarke also issued 27 free passes, including posting a dismal 7.9 BB/9 in 28.1 High-A innings.
From the Cardinals' perspective, it makes sense why they would target these two arms. Fitts can slot right into their rotation and might benefit from the spacious Busch Stadium, and Clarke will immediately become one of their highest-upside prospects. For the Red Sox, meanwhile, the fact that they were willing to part with these two arms speaks to how much better their pitching depth has become in recent years. Fitts has been passed on the Triple-A depth hierarchy by the likes of Kyle Harrison, Hunter Dobbins, and Cooper Criswell, while Clarke has not developed at the same pace as fellow left-handed prospects Connelly Early and Payton Tolle.
Red Sox's Work Isn't Over Despite Sonny Grade Trade Being a Win
In a vacuum, the Gray trade is a win for both sides and makes the Red Sox a better rotation than they were yesterday. Yet to properly evaluate this trade, one has to judge Gray based on Breslow’s own comments from the GM meetings.
“Because of the depth that we’ve built up over the last couple of years, we feel pretty good about overall starting pitching and Nos. 3-ish through 10-ish, and that’s not to take away from guys who are certainly capable of doing more,” Breslow said. “It’s just to say, I don’t think we’re going to spend a ton of time trying to add a No. 4 or a No. 5 starter. If we’re going to make a starting pitching addition, I think it should be somebody who can pitch at the front of a rotation and start a playoff game for us.”
There is no question that Gray has been that guy in the past, but whether he can be a legitimate number two starter in 2026 remains to be seen. As good as Gray has been over the past four seasons with the Twins and Cardinals, the American League East is a completely different animal, and Gray has struggled in his career at both Fenway Park and Yankee Stadium.
- Fenway Park: 0-4, 6.84 ERA in seven games (six starts, 26 1/3 innings)
- Yankee Stadium: 6-7, 6.06 ERA in 22 games (18 starts, 101 innings)
It’s also worth noting that Gray has seen his average fastball velocity drop in two consecutive seasons, going from 92.9 miles per hour in 2023 to 91.7 miles per hour last season. While he has been able to adjust by leaning more heavily on his elite sweeper, that fastball was one of the worst pitches in baseball last year, getting battered to the tune of a .376 average and a .594 slugging percentage.
None of this is to say that Gray can’t still be an effective starter, but it’s worth tempering expectations headed into his age-36 season. His 2026 STEAMER projections (31 GS, 3.68 ERA, 3.9 fWAR) are more indicative of a really solid mid-rotation arm rather than an elite Crochet running mate. With ample resources to make another big splash in either free agency or with another trade, along with their stated desire to build a team capable of winning the ultra-competitive AL East, it would be a disappointment if Gray were the only starter the Red Sox acquired this winter.