Sonny Gray Changes Teams. Again.

The Boston Red Sox have acquired veteran right-hander Sonny Gray and cash from the St. Louis Cardinals, in exchange for pitchers Richard Fitts and Brandon Clarke, and either cash or a player to be named later. Seems straightforward enough.

After 13 seasons in the majors, you all know Gray by now: short guy out of Vanderbilt. Big, slow curveball, but not a ton of velo. Changes teams every two or three years. In those 13 seasons, Gray’s two best WAR seasons are 5.4 and 4.5, but he’s posted four additional seasons of between 3.5 and 3.9 WAR, and three others of between 2.4 and 2.7 WAR. This is the Toyota Sienna of pitchers: You don’t stay up nights dreaming about him, and he can be a little pricey, but he’ll get you and your family where they need to go with an absolute minimum of fuss.

The Red Sox made the playoffs in 2025. I don’t think I’m going out on a limb by assuming they’d like to make the playoffs again in 2026. If I were in the playoff-making business, I’d welcome the opportunity to add Sonny Gray to my team.

Gray came into the majors with a decent amount of hype; he came from what I’d call the second generation of elite prospects to develop under Tim Corbin at Vandy. (It’s about 50/50 that Gray will pass David Price to become the all-time career WAR leader among Vandy alums sometime in 2026. Once that happens, he should retain that title until and unless Dansby Swanson hangs around long enough to haul him in.)

Early in Gray’s career, when he was putting up big innings totals and finishing on the Cy Young podium for the Athletics, I wasn’t a massive fan. I thought he didn’t get enough strikeouts to count as a legit no. 1 starter. Indeed, even now you wouldn’t want him to start Game 1 of a playoff series, but good news, Boston already has Garrett Crochet for that. And if Gray’s starting, say, Game 3, that’s a good sign for your rotation.

In recent years, Gray has started leaking fastball velocity — as most pitchers in their mid-30s do — but he’s compensated by leaning into a cutter and changeup, making him a legit six-pitch pitcher since 2023. At the same time, he’s gone the right way with his strikeout and walk numbers. During his time with the A’s and Yankees, Gray struck out 20.9% of opponents and walked 8.2%. In two seasons with the Cardinals, he struck out 28.4% of opponents and walked 5.4%.

The Cardinals, who are probably not in the playoff-making business at the moment, signed Gray to a three-year, $75 million contract before the 2024 season, leaving one year and $25 million worth of AAV, plus an option, left to run. Consider the pitchers who just accepted the qualifying offer of $22.025 million over one year: Brandon Woodruff and Shota Imanaga. I’d rather have Gray than those guys.

Which is not to downplay the risks of hitching one’s wagon to a 36-year-old right-hander whose fastball averaged just under 91 mph last season. Gray also posted a 4.28 ERA in 2025, which is his worst figure since 2018. Now, his FIP was nearly a full run better, and a lot of the ERA damage was confined to a few truly disastrous starts, but that’s still worth keeping in mind.

Then there’s the contract situation. Because Gray’s three-year contract didn’t call for a straight-up $25 million salary; it paid him just $10 million in 2024, $25 million in 2025, and was due to pay him $35 million in 2026, with a further $5 million guaranteed in the form of an option buyout.

That’s ludicrous. If Gray’s contract were any more backloaded, Big Sean would be writing songs about it. That’s how shady rent-to-own appliance stores price out refrigerators. Lucky for the Red Sox, they checked the ledger before they called in the trade, and were able to restructure Gray’s deal and get the Cardinals to kick in $20 million in cash.

Gray will now get paid $31 million for 2026, with a $10 million buyout of a mutual option for 2027. (The extra $1 million is for waiving his no-trade clause.) With the Cardinals’ contributions, that leaves Boston to pay $21 million for one year of Gray.

That strikes me as a reasonable amount to pay Gray in 2026. And by eating about half of Gray’s total remuneration, the Cardinals have turned this into a baseball trade, rather than a salary dump.

So let’s check in on the guys they’re getting back.

Fitts, the man whose name invites a million lascivious puns, has been in and out of Boston’s rotation over the past two seasons, with mixed results: a 3.97 ERA and 5.02 FIP over 65 2/3 career innings. Fitts, who turns 26 next month, was a sixth-round pick out of Auburn in 2021.

Longtime Effectively Wild listeners might remember Fitts from the Meet a Major Leaguer segment on Episode 2216, where I guest-hosted and bored Ben to death with the fun fact I’m about to share with you: Fitts’ older brother Trevor was the Game 1 College World Series Final starter for Mississippi State in 2013. He — along with Hunter Renfroe, Kendall Graveman, Adam Frazier, and about 25-odd other guys — made up one of the dirtbaggiest, most mullet-having, possum-chasing teams in baseball history.

The hitting coach from that team, Nick Mingione, is now the head coach at Kentucky, where Trevor Fitts currently serves as director of player development. The pitching coach, Butch Thompson, was Richard Fitts’ college head coach at Auburn. Networking is important, people.

I guess the fact that I just spent two paragraphs talking about Fitts’ brother’s post-playing career job history tells you something about Fitts as a pitcher. He’s got a mid-90s fastball with some natural cut, and three breaking pitches. His slider, it’s worth pointing out, got absolutely wrecked in 2025: opponents slugged .635 off the pitch last season.

Fitts is a bit of a project; with his fastball shape, he needs something with arm-side movement, and the Red Sox weren’t able to find it for him. He went with a splitter in 2024, and a sinker-changeup combo in 2025, but didn’t throw any of those pitches more than 11% of the time. If the Cardinals can find an off-speed pitch that works for him, he’s got the physical tools and command to start.

And even if the Cardinals don’t find an off-speed pitch that works, Fitts might end up starting quite a bit. With Miles Mikolas moving on and Gray now out of the picture, the Cardinals have created a universe where “Opening Day Starter Andre Pallante” is a realistic possibility. If nothing else, Fitts can muscle through a lineup a couple times and keep the game moving through five innings, even if he gives up a few runs along the way. Plus he’s still young, with two options and six years of team control left. It’s nice to have depth like that.

But the real prize in this deal, for St. Louis, is Clarke. Eric Longenhagen informed me that while this Brandon Clarke is not the same Brandon Clarke who plays forward for the Memphis Grizzlies, he does have basketball player-like 7-foot-4 extension off the mound. Here’s more from Eric:

Clarke was a junior college prospect committed to transfer to South Carolina, but his arm strength improved throughout 2024, and he properly blew up at that year’s Draft Combine, where he touched 98 and sat 95-plus. He signed for $400,000 and then showed even bigger stuff at the start of 2025 — Clarke was touching 100 and had an unbelievably nasty new slider — which moved him into the 50 FV prospect tier despite command and injury-related relief risk.

And Clarke’s injury history is lengthy. He had Tommy John in high school and surgery for Thoracic Outlet syndrome while he was a freshman at Alabama (he never pitched in games there), and he dealt with a stress fracture in his shoulder at State College of Florida. In 2025, Clarke dealt with blisters; he missed a month in May/June but wasn’t formally put on the IL. After Clarke returned from that dark month, he never pitched beyond the third inning of any outing, and in mid-August, he again dealt with a blister and this time was actually put on the IL.

Clarke’s injury history and imprecise feel for location make it likely that he ends up a reliever. But he might be a really great one, potentially one of the best left-handed relievers in all of baseball. He’s sitting 97 for multiple innings, and aspects of Clarke’s delivery, including things the Red Sox have tweaked since drafting him, help it play up. This guy generates seven feet, four inches of extension, he delivers from a low arm slot but has a vertical hand position on release (creating both uphill plane and ride), and the Red Sox made his delivery more cross-bodied and deceptive than it was in college. The angle on his fastball is a nightmare, especially when it’s located around the hands of lefties.

Clarke was a curveball/changeup guy at the Combine, but now has a lethal upper-80s slider that will crest 90 mph with huge length, and it also plays up against lefties because of the changes made to his delivery. I thought he had the makings of a good changeup at the Combine, but that pitch was barely featured in 2025 because Clarke didn’t need it in his relatively short outings. He merits development as a starter just to see if things work out, but in all likelihood, Clarke’s future rests in late-inning relief. But don’t let the relief projection undersell his prospectdom. This is the sort of stuff you see at the end of games in October, monstrous, overwhelming, door-slamming stuff.

That’s quite an evocative prospect profile, but one riddled with enough risk that you understand why the Sox were willing to part with Clarke.

Ultimately, how we remember this trade in five years — if we remember it at all; Gray gets traded a lot and they’re all starting to run together — is going to depend mostly on how good the Cardinals’ pitching development is.

For one extremely expensive year of an aging starter, in a season where finishing over .500 would probably be a pleasant surprise, the Cardinals have acquired a potential back-of-the-rotation starter and a potential elite high-leverage power left-handed reliever. Or, they’ve acquired a replacement-level swingman and a circus act who can’t throw enough strikes or stay healthy enough to get over the middle rungs of the minor league ladder.

For that reason, I can’t declare this trade to be a robbery in either direction. It’s a fair deal with both upside and risk for everyone involved. Well, except Gray. He just got paid an extra $1 million to dramatically increase his chances of pitching in the postseason in 2026. That’s a pretty sweet deal.