Playing MLB trade deadline matchmaker: 10 players and teams that just make sense together

We are less than a week away from the 2026 MLB trade deadline. There has been only one notable trade so far ( the Connelly-Early-for-Curtis-Mead swap ), but more are on the way. The smaller moves will trickle in these next few days before the biggest moves go down just before Monday's 6 p.m. ET deadline. The muddled standings, however, have made buyers and sellers harder to distinguish .

With all that in mind, let's lay out some hypothetical trades we think make sense with the deadline a week away. To be clear, these are not predictions ( we've already done those ). These are player-to-team trade scenarios that we think make the most sense and that we'd like to see before Monday's deadline. Got it? Good. Let's get to it.

I'm a little frustrated by the Brewers , who have been one of the best teams in baseball the last few years but haven't done a whole lot at the trade deadline historically. Last year, they added Danny Jansen , Brandon Lockridge , and Shelby Miller at the deadline (and Andrew Vaughn in June). Two years ago, they added Frankie Montas and Nick Mears . Three years ago, it was Mark Canha , Andrew Chafin , and Carlos Santana . All fine moves in a vacuum, but not all-in "we want to win the World Series" moves.

The Brewers are again one of the best teams in baseball this season, and in our "moves we'd like to see" universe, I think there should be motivation to bring in Tarik Skubal , who can swing a postseason series on his own. Christian Yelich is maybe starting to show his age. William Contreras will be a free agent after next season, which, in Brewers World, means he'll be a trade candidate this offseason. Jacob Misiorowski won't be this forever (or will he?). The farm system is very deep and Skubals are not available every trade deadline. This is a good time to make that all-in move and try to get over the hump and win a World Series.

The upstart White Sox need a controllable starting pitcher more than they need a controllable closer, but they can get both, right? This is a team on the cusp of perennial contention thanks to its young position player core and strong farm system, which recently added 2026 No. 1 pick Roch Cholowsky . Trade for Mason Miller now and he's in on the ground floor, and you have a fierce 1-2 punch at the end of games with him and Grant Taylor . The White Sox would be playing six-inning games in October, given Taylor's ability to go multiple innings.

It might be now or never for the White Sox and Miller. If he doesn't move at the deadline, more teams figure to get in on the bidding in the offseason. Teams that aren't in the race now but will go into the winter with designs on contention in 2027. The Blue Jays , the Mets , etc. Add Miller now, sign a starter or two in the offseason, and the White Sox will have a chance to enter the "best team in the American League" conversation as early as next season. It's a win-now and win-later move given Miller's three additional years of team control.

It is more likely the Cubs trade for Freddy Peralta , who knows manager Craig Counsell well from their time together with the Brewers, but I think Clay Holmes is simply the better pitcher right now. Higher quality stuff, better bet to give you innings, more adaptable if you want to use him out of the bullpen. Holmes hasn't appeared in an MLB game since a comebacker broke his leg on May 15, but he made a ( heavily scouted ) minor-league rehab start on Tuesday and should be big-league-ready soon. Peralta is the sexier name and he's had the better career up to this point. Right now, though, for the rest of 2026, give me Holmes. He's the Mets pitcher the Cubs should target, not Peralta.

This almost feels fait accompli . The Yankees badly need a catcher, specifically a right-handed hitter, and Ryan Jeffers is exactly that. He's a rental too, so even though the Twins are hanging around the wild-card race, they could justify trading him rather than losing him for nothing in the offseason. Minnesota has carried three catchers since Jeffers came off the injured list on July 10 (also Victor Caratini and Alex Jackson ). In one move, they can clear that logjam and import young pieces who can help with the postseason push right now, not necessarily prospects who are two or three years away. The Yankees get the righty-hitting catcher they need and the Twins turn their most obvious trade chip into younger, more long-term pieces.

A power-hitting outfielder would make more sense given how few homers the Rays get from players other than Junior Caminero . There aren't many of those available, though, plus Luis Arraez better fits Tampa's extreme contact approach. They haven't gotten much offensively from second base at all this season. Arraez fits like a glove. He lines up offensively and positionally, especially if you buy into his improved defense. This is one of the more obvious trade matches of the summer.

If the Tigers trade Skubal, something that seems increasingly likely , they might as well trade Casey Mize too. He's another rental. The Braves really need another starter to buttress a rotation that is counting a little too much on Bryce Elder and Martín Pérez these days. Mize's ongoing groin issue (he's currently on the injured list for the third time this season with it) is the X-factor here. For our purposes, we'll assume the Braves or whichever team trades for him are comfortable with the medicals. Mize has been terrific when healthy this year and might be a better bang for the buck than Skubal, given the potential asking prices.

Phillies right fielders have been among the worst in baseball and their right-handed hitters have, literally, been the worst in baseball by OPS. This team badly needs a right-handed-hitting outfielder, which, unfortunately, is a profile in short supply. Lane Thomas is a solid enough all-around player who will help offensively, defensively, and on the bases. He's better as a platoon guy than as an everyday player, but, in this market, Th...

Indexed and credited by AIPROPX. Originating outlet: CBS Sports. Open at source →