For the next few weeks we’ll be doing some theorizing on optimal returns at the trade deadline as the Red Sox look to do another tear down amidst a hopeless season. This week, it’s Sonny Gray—and unlike last week’s Chapman conversation, this one comes with a wrinkle.
Week two of Sock Drawer. Last week it was Aroldis Chapman and a relatively clean simulation—the Sox have the asset, contenders want it, Breslow sets the price. This week is messier, because Sonny Gray has a no-trade clause, and that changes the whole conversation.
Gray has been one of the few things working on this roster in 2026. This season, he’s commanding a 2.69 ERA, 1.11 WHIP, 75 strikeouts across 83.2 innings. He’s somehow 9-1. On a team that’s going nowhere and gives NO support for its starting pitching. As a 36-year-old who wasn’t supposed to be anyone’s ace, that’s not a just real asset. That’s a legitimate AL Cy Young contender, and the market is starting to understand what it’s looking at. The Braves, Cubs, Brewers, Giants, and others are already circling. Jon Heyman has Atlanta’s name attached.
The complication is clearly the NTC. Gray restructured his contract when he came to Boston—the Cardinals are covering $20 million of his $31 million salary, meaning an acquiring team only owes the prorated remainder plus a $10 million buyout on a mutual option. That’s manageable. But Gray gets final say on the destination, and he’s been measured about it: “If someone came to me from the Red Sox and made a decision that that’s the direction this team was going to go, I would be open for a conversation.”
Open for a conversation is not a yes. The Sox can’t just shop him to the highest bidder. The field narrows to places Gray would actually approve. Frankly, I don’t blame Gray for being measured about it. I would think even for his age and long career, staying settled in one city might be more important to him and his family than title chasing.
The whole situation is actually fine if you’re looking at things from Craig Breslow’s perspective. The teams that make sense for Gray make sense for the Sox, and the NTC creates a different kind of leverage. The places Gray would approve are serious contenders with real farm systems (for the most oart), and serious contenders with real farm systems don’t get to lowball you. If you’re smart.
One more complication: Connelly Early just went to the IL with an elbow injury. On the surface, you might think that makes Breslow more reluctant to move Gray, now that the rotation has lost two legitimate arms and he’s even more exposed. That’s not wrong. But on a team that’s going nowhere, “we need pitching depth” is not a reason to hold a guy you can turn into a top prospect or a real bullpen piece. Early going down hurts the on-field product. It doesn’t change the deadline ethos.
There’s also a decision Breslow has to make before he picks up the phone: how much salary relief is Boston putting in? The answer to that question changes the return completely.
If Boston eats a chunk of salary: the acquiring team’s cost drops, Gray becomes easier to move, and the Sox can push for a real prospect from the top of the system.
If the full contract goes with him: the team absorbs more cost, and what comes back is an MLB piece, a bullpen arm who can contribute now rather than a name on a list, but isn’t the most valuable in general.
Neither is wrong, it just depends on what Breslow thinks this team needs more. I’ll give you both just to show you what that means.
Braves
Eats salary — Owen Murphy (RHP)/Tate Southisene (2B/SS)
Full salary — Dylan Dodd (LHP)/Dylan Lee(LHP)
Atlanta is the most obvious match here and maybe the most likely destination if this deal gets done. Their rotation is beaten up more than a room in Magic City—Spencer Strider, Joey Wentz, Spencer Schwellenbach, AJ Smith-Shawver are all missing some time—and the Braves are still contending, which means they need a real arm, not a depth add. Gray is exactly that.
The NTC nearly solves itself. Gray is from Nashville. Atlanta is close, the organization is stable, and the Braves have been in October almost every year for half a decade. If I were him, I would approve this one. Breslow knows that and should price accordingly. The fact that Gray probably says yes to Atlanta when he might say no to someone else is leverage, not a concession.
Murphy is the arm I want here. He dominated High-A in limited action before the injury, has one of the higher ceilings left in an admittedly thin Braves system, and fits the pitching-for-pitching logic cleanly. If Atlanta pushes back on Murphy, Southisene is the alternative, different profile, still a legitimate top-five piece from a system that isn’t deep enough to be holding onto anyone. The Braves farm being ranked near the bottom of the league is exactly why the salary relief matters here. Boston is making the deal easier in exchange for a sweetened pot.
If the full salary goes with Gray, Dodd gives you a back-end MLB starter with some upside who could slot into a Boston rotation that always needs arms. Lee is the more established bullpen piece, lefty, track record, knows how to get hitters out. Either is a legitimate MLB contributor, not a lottery ticket. In a year where the Sox bullpen has been a problem, adding a proven arm to that mix has real value even if it doesn’t change the rebuild timeline.
Cubs
Eats salary — Jaxon Wiggins (RHP)
Full salary — Phil Maton (RH) or Porter Hodge (RHP)
Chicago’s rotation is a mess and they know it. Two Tommy Johns, two hammies, a neck, a back, you may as well walk into the recovery ward of any ER Northside and see the venerable Cubs starting rotation. They had to trade for David Peterson just to stay afloat right now! If the Cubs are going to make a run, they need another reliable starter, and Gray is the definition of a reliable, veteran presence, experience in big games, innings-eater who won’t need to be pulled in the fourth. The fit is clean.
The double-package angle is worth noting: there’s real reporting floating around that Chicago could go after both Gray and Chapman in the same deal. Whether that’s actually on the table or just a fun idea that got written up is unclear—I get it with Chapman winning the WS in 2016 with the Cubbies—but if Breslow can work that angle, he should. Two complementary needs from one buyer is a GM’s dream negotiation.
Wiggins is the one I want from Chicago. He just cracked the top 100 and the scouting reports have gotten genuinely interesting, the stuff was always there, now the polish is catching up. The Cubs system has thinned out from where it was a couple of years ago (Shaw and Horton graduated, Caissie got traded), which makes Wiggins the clear headliner of what’s left. Pitcher for pitcher makes the most sense for both sides.
Full salary to Chicago means pushing for Maton or Hodge. Maton is a power arm with swing-and-miss stuff who would fit well in the back of a Boston bullpen that needs exactly that. Hodge is the younger option with more upside but less certainty. Either gives the Sox a real MLB reliever back, which is a reasonable ask when you’re handing over a $21 million arm and not asking for a cent back.
Brewers
Eats salary — Jett Williams (SS/CF)/Bishop Letson (RHP)
Full salary — Aaron Ashby (LHP)/Abner Uribe (RHP)
Milwaukee is the most interesting team in this conversation that isn’t getting talked about enough. The Brewers have the best farm system in baseball, by most accounts the best in years, and they’re contending, which means they need what Gray provides. They also develop pitching better than almost anyone in the sport. A guy like Gray going to Milwaukee under their coaching staff could buy him another productive season-plus.
The Brewers tend not to overpay at the deadline—it’s an organizational strength of theirs, which means Breslow has to go in knowing his floor. But their system is deep enough that they can give up a real piece without gutting themselves, and that’s exactly the kind of trade partner you want.
Williams is the intriguing prospect here. Traded to the Brewers from the Mets in the Freddy Peralta trade, his ranking has slipped slightly but the tools are still there and Milwaukee’s development track record means the ceiling hasn’t closed. Letson is more of a pure pitcher profile with a legitimate shot to move fast. Either way, the Brewers have the depth to make this hurt a little, and when the top farm system in baseball is making a move hurt, that’s a good outcome for the Sox. I’ll also say this: I really want Shane Drohan back. Boston drafted him, developed him, and then let him walk. If there’s any version of this deal where Drohan is part of the return, I’m listening.
Ashby is the name on the full-salary track. Lefty, swing-and-miss, already knows how to pitch at the big league level. He’s exactly what the Sox bullpen needs and the Brewers have the depth to absorb losing him. Uribe is the higher-upside option: the stuff plays in high leverage and if he figures out the command piece, he becomes someone. Either way, Milwaukee has the bullpen to send a real piece back without hurting their October chances.
White Sox
Eats salary — Hagen Smith (LHP)/Tanner McDougal (LHP)
Full salary — Sean Newcomb (LHP)/Grant Taylor (RHP)
Here’s the one nobody is writing about. The White Sox have been one of baseball’s most historically futile franchises for the better part of a decade. Multiple 100-loss seasons. A rebuild that took forever and delivered mixed results. Guaranteed Rate Field on a Tuesday. None of that sounds like a Gray destination.
Except they’re leading the AL Central right now.
That changes everything about this conversation. Chicago isn’t calling Boston because they’re stockpiling assets for three years from now. They’re calling because they have a pennant race on their hands for the first time in years, a market that has been starved for relevance, and a front office that knows exactly how rare and fragile first place feels when you’ve spent most of your recent history losing 95 games. A team in that position does not let a shot at Sonny Gray pass them by.
The NTC is the real question here. Gray has to approve the destination, and Chicago’s recent history is not exactly a draw. But if the White Sox are still in first at the deadline, that’s a different conversation than it would have been in April. Pitchers want to pitch in October. Gray says he’s open to a conversation. A first-place team with a real need is the kind of conversation that moves the needle on a waiver.
The farm depth is real too. All those top draft picks from the losing years are still in the system. Smith is already in the top 100 and has the profile of a back-of-rotation starter with real MLB durability. McDougal is the longer-range bet, younger, rawer, higher ceiling if the stuff develops. The Sox adding another lefty arm to the system is never a bad thing given how they develop pitching.
The full-salary version of this deal is the one I find most interesting. Boston could have a funny reunion on their hands. Newcomb returning to the organization would be interesting, and he’s been more effective in this stint than his previous run in Boston that the Sox would have something to work with. Taylor is the option if Newcomb isn’t available, left-handed, serviceable, fills a need in a pen that has needed help all year.
Giants
Eats salary — Gavin Kilen (SS/2B)
Full salary — JT Brubaker (RHP)/Sam Hentges (LHP)
San Francisco is the most interesting team on this list and probably the most overlooked one. Tony Vitello took over as manager this past offseason, coming straight from Tennessee where he built one of the better college programs in the country. He doesn’t have the personal history with Gray that Bob Melvin did, so the NTC approval is less certain here than it might have been a year ago. Oracle Park is a great place to pitch, San Francisco is a good market, and the Giants are a respectable organization—Gray could do a lot worse. But this one is a harder sell than Atlanta, and Breslow should know that going in.
What makes San Francisco interesting is Gavin Kilen.
Kilen was a Red Sox draft pick. Boston selected him, he went back to college (Louisville first, then transferred to Tennessee), and now he’s a top-five piece in the Giants system. The Tennessee connection is the thread that makes this section worth writing: Vitello coached Kilen with the Vols before taking the Giants job. So you have a manager who knows this prospect intimately, which cuts both ways — Vitello may be the last person who wants to trade him, or he may be exactly the person who knows what Kilen is and isn’t at the MLB level. Either way, Breslow has leverage in asking, because the Giants need rotation help and the Sox hold the asset. He’s the name I want from San Francisco if Boston is putting money in. Jacob Bresnahan and Blade Tidwell are also in the top-five conversation if Kilen isn’t available, Bresnahan is a sneaky-good lefty who keeps getting better, Tidwell has the stuff to move fast.
Brubaker is the headliner on the full-salary track, a legitimate MLB arm who gives the Sox a real contributor and not a project. Hentges is the alternative, left-handed and serviceable, fills a pen need. Carson Whisenhunt is worth a mention too: still a top-30 Giants prospect but he’s been down in Triple-A and could be framed as MLB-ready depth, which makes him an interesting piece that straddles both tracks.
With the tsuris Buster Posey has put himself through this season alone in the Bay Area, I could see Breslow actually end up on the right side of a deal between these former players here. We’ll give Devers to Posey, even with the drama there of late.
Atlanta is the deal that should get done and probably will. Gray approves it, the Braves need it, and the NTC leverage means Breslow can squeeze them. Cubs are the second call because of the double-package angle and the Wiggins possibility. Brewers are the sleeper with the best farm in the sport.
The Giants are the wildcard. The NTC approval is probably the easiest of any team on this list, and the Kilen homecoming angle is the best narrative piece in this whole conversation. The White Sox are the sleeper. Nobody is putting Chicago in this conversation right now, and that’s exactly why Breslow should. A franchise that’s been irrelevant for years just found itself in first place and they know the window could slam shut by September. That’s panic-buy energy, and panic-buy energy gets you Smith or McDougal. Make all five teams think the other four are ahead of them. Then close the right deal.
The salary decision is the only open question. If Breslow is building toward the deadline as a genuine rebuild, eat the salary, get the prospect, add to the system. If he thinks this team has a window to compete sooner than the standings suggest, take the MLB piece and plug the bullpen. Both are defensible. Just know what you’re doing before you pick up the phone.
