Let’s Make Some Deadline Trades! (2026 Edition)

If you’re a baseball fan, the end of July means one thing: Trades. That’s right, we’re less than a week away from this year’s deadline, which is set for Monday at 6 p.m. ET, and there’s plenty of action still to unfold. Even a real snoozer of a deadline tends to have at least a few big deals, and so far, the only real needle mover swap made was the fascinating challenge trade that sent Connelly Early from the Red Sox to the Nationals for Curtis Mead.

While we don’t know precisely what will actually happen, since there are no such things as oracles, we have an idea that something will occur, making the trade deadline the ideal time for wish-casting and imagineering. As I do every year, I whip up some trade scenarios that are plausible and productive. We usually get fun additional trade discussion in the comments, so make sure to check those out and maybe even add your own. I’d also suggest letting me know when I give up too much or too little in a trade.

The Los Angeles Dodgers acquire SP Tarik Skubal from the Detroit Tigers for SP Emmet Sheehan, OF Zyhir Hope, and OF Ching-Hsien Ko.

I think in the end, the Tigers will trade Tarik Skubal for the best package they can get. Sure, they’ve snuck into the back of a lackluster AL wild card race, but is sneaking into the playoffs at 80-82 really worth losing what they would get in return for their ace? The Dodgers are a team that likes pushing in their chips to add a legitimate star, and in their quest to snag the first World Series three-peat of the 21st century, getting Skubal would be an all-in move. Emmet Sheehan is a good enough starting pitcher that trading Skubal for him wouldn’t necessarily signal a complete surrender, and because he’s under club control through the 2029 season, the Tigers would be adding someone who could boost their rotation for the next few years, too. Zyhir Hope is an excellent prospect, but Josue De Paula and Mike Sirota are both ahead of him in the pecking order for the Dodgers, whereas in Detroit, he could easily be in the 2027 starting lineup. That’s already a lot of value for Skubal, I feel, so the last inclusion is a relatively low-impact prospect in Ching-Hsien Ko, who at only 19 years old is already a pretty big dude — listed at 6-foot-3 and 215 pounds. Ko has real power upside and could have more value for an organization like the Tigers, who I don’t think will want to be on the Spencer Torkelson train much longer.

The Chicago Cubs acquire SP Sandy Alcantara from the Miami Marlins for CF Kane Kepley, P Dominick Reid, and P Mason McGwire.

Coming into the season there was real cause for concern about the Cubs’ pitching staff, and those worries have only increased since April. Cade Horton is out for the season, and Justin Steele’s recovery has been slow enough that if he gets major league innings at all this year, they’re almost certainly not going to be as a starter. Ben Brown and Edward Cabrera are both expected to return from their injuries, but if there are any setbacks, it’ll be too late for the Cubs to acquire a pitcher to replace them. For that reason, now’s the time for Chicago to add one. Alcantara has not returned to his pre-injury form, but he throws a lot of innings, something every team needs, and the Cubs have a defense good enough that they ought to worry less than almost every other team in baseball about all the balls in play that he allows. ZiPS projects Alcantara to put up more 2027 WAR playing for the Cubs or Cardinals than any other team, and I don’t think the Cardinals are going to be aggressive buyers, leaving the Cubs as the best fit.

Unlike a rental superstar like Skubal or a regular star with a year or two of cost control, the Marlins shouldn’t expect a haul for Alcantara. But Kane Kepley is a very good outfield prospect who is a bit redundant on a Cubs team that employs Pete Crow-Armstrong. I think the Marlins will insist on getting back some pitching in the trade, but I don’t think the Cubs would even consider giving up someone like Jaxon Wiggins for Alcantara. Dominick Reid and Mason McGwire are real prospects, just not at the top of the food chain in this system.

The Milwaukee Brewers acquire SP Freddy Peralta from the New York Mets for 1B Blake Burke and OF Jett Williams.

I swear that I’m not just trying to troll by undoing part of the Freddy Peralta trade, as this is a swap that would make sense for both clubs. This season is all but officially over for the Mets, and Peralta is headed to free agency after the World Series. He’s been mediocre enough that they are not going to get any top prospects for him unless a team absolutely loves him. The Brewers are obviously quite familiar with him and may be in the best position to get him back to typical form for the last two months. But even if he isn’t the ace he was last year, he is someone that can eat some innings down the stretch, which is highly useful given Milwaukee’s young rotation. Jett Williams has lost a lot of his prospect value this season, but if he claws any back, there are more open spots for him next year with the Mets than with the Brewers. Blake Burke is an interesting prospect who is close enough to the majors to have some appeal to the Mets, who don’t appear to be counting on Mark Vientos for much of anything at this point. If Burke hits his upside, he’d certainly provide some value for the Mets in the near future, but he probably doesn’t bring enough to the table that the Brewers would refuse to include him in a trade for Peralta. I’m more optimistic on Burke than ZiPS is, and less optimistic on Williams.

The Chicago White Sox acquire 1B/DH Rafael Devers from the San Francisco Giants for SS Billy Carlson, with the Giants paying a whole lot of money in the deal.

The Giants haven’t finished above .500 since that wacky 2021 season, and I suspect that they’re at the stage where they’re going to cut their losses with some of their veterans. Rafael Devers has hit quite well since a miserable April — entering play Monday, he’s slashing .265/.347/.570 with 20 home runs and a 147 wRC+ across 317 plate appearances since the start of May — but if he were a free agent this offseason, I practically guarantee that nobody would offer him a seven-year contract worth $211 million, about what he’s owed after this season. Even so, I think the right suitor would be happy to pay him half of that. The White Sox still have a good farm system after their various graduations this year, but they don’t really have a lot on the easy side of the defensive spectrum, and Devers would be really fun as the DH for the Sox. Bringing in Devers to take Andrew Benintendi’s playing time would greatly improve Chicago’s offense, and he’s simply better suited for Guaranteed Rate Field (I really hate writing that name) than Oracle Park. Plus, since I’m a student of history, it feels a bit like adding Richie Zisk as a modern take on the South Side Hitmen. Since the Giants are paying a truckload of cash in the deal, I’m having them pay enough to actually get a pretty decent prospect, Billy Carlson, in return.

The Cleveland Guardians acquire OF JJ Bleday and 1B Nathaniel Lowe from the Cincinnati Reds for OF Kahlil Watson, C Jacob Cozart, and RP Franco Aleman.

I still sort of like Kyle Manzardo, but he’s been absolutely dreadful this season, as has Rhys Hoskins, making for a really depressing platoon at first base for the Guardians. If they’re going to have another miracle second half, they need to find offense right now, but it’s unlikely they’ll blow a huge hole in their budget or farm system to do so. Considering these constraints, JJ Bleday and Nathaniel Lowe both represent real short-term improvements, and Bleday can stick around after the season as he’ll be entering only his second year of arbitration eligibility. I feel this represents a pretty good return for two very low-key signings this spring, as Kahlil Watson’s cup of coffee in the majors isn’t indicative of his power-speed upside. The Reds could use Jacob Cozart as a stopgap catcher to tandem with Jose Trevino in 2027 with Tyler Stephenson heading for free agency, and Franco Aleman is an interesting reliever, though raw enough that it would be hard for the Guardians to trust him with high-leverage innings right now.

The New York Yankees acquire C Tyler Stephenson, SS/3B Tyson Lewis, and OF Dane Myers from the Cincinnati Reds for SS Anthony Volpe.

If there’s a way to get Anthony Volpe back to the player it looked like he’d be a few years ago, I’m not sure the Yankees are the organization to help him figure it out. So it might make sense at this point to get some value for Volpe as he heads into his last two years of team control. I still like Austin Wells long term, but the catcher position has been downright ugly for the Yankees this year, and they could use some short-term depth in their injury-depleted outfield. I think Tyler Stephenson and Dane Myers could fit the bill, and Volpe still has enough upside potential that a real prospect, though not a top one, ought to be included rather than only an OK short-term rental and a fourth outfielder. Tyson Lewis is a ways off, but he fits the bill as a potential power-speed combo infielder. I’m not sure the Reds want to keep waiting for the revival of 2023 Matt McLain, and I’d be interested to see them try out Volpe at second.

The Arizona Diamondbacks acquire SP Kevin Gausman from the Toronto Blue Jays for OF Druw Jones and SP Mitch Bratt.

For a while, I thought the Blue Jays would get things back on track, but at 19-27 since the start of June, they’re as close to having the worst AL record as they are to a playoff spot. Considering all the talent on their roster and how close they came to a World Series last year, the Jays are unlikely to blow up their team and initiate a rebuild, but Kevin Gausman is a free agent at the end of the season, making him expendable. The Diamondbacks could use a bat, but I’ve already given the most interesting ones away — the Astros aren’t trading Yordan Alvarez — and another pitcher would be equally welcome. Druw Jones isn’t the prospect he once was, but the Jays could use some long-term outfield depth, especially of the athletic variety, and the organization has a long history of accumulating close relatives of former big leaguers. That being said, Jones probably isn’t enough, and his first-round hype is about gone at this point, so I’m also sending Mitch Bratt, who has struggled in his debut in Arizona. I still think Bratt will be a decent third or fourth starter and innings eater, but his ceiling is limited. I don’t love him as much as ZiPS does.