The 2026 MLB trade deadline has come and gone. There were many moves, some of them big, some of them small, many of them graded by me right here on this very website. But it’s all over, and save for a couple of minor league elevations here and there, these are the teams everyone will take into October. Tarik Skubal is on the Los Angeles Dodgers, Adley Rutschman is on the Boston Red Sox absolutely nobody… okay, Heliot Ramos, is on the New York Yankees. What a time to be alive!
As is tradition, we will now embark on naming some winners and losers of said trade deadline, but I’m going to wax poetic about the format real quick: “winners and losers” is a great way to encapsulate these massive decision-making periods that sports are obsessed with; trade deadlines, the first day of free agency, the transfer window in soccer — we love them. But it is also impossible to actually “win” or “lose” the deadline on the day of the deadline, which is when I’m writing this. MLB decisions are like those of Bene Gesserit in Dune: plans are measured in centuries, and prospect returns can include guys who may not debut until, like, 2030 or something crazy.
The following “winners” and “losers” are thus merely my opinion about what MLB teams did (or did not) do on and around August 3, 2026, and how I believe they will play out. It’s not that I could be wrong, but that I will be wrong — I’m just not quite sure about what yet.
Winner: Los Angeles Dodgers
(imagine the following paragraph read in as monotone a voice as possible) I am contractually obligated to begin the column with this but will not be spending any more time on it than I have to. The Dodgers traded for Tarik Skubal, the best pitcher in the world, to add to their back-to-back World Series champion roster, raising their odds of a three-peat from “really high” to “really high.” Congratulations to everyone involved.
Welcome to the other side of the coin. The Brew Crew came into the deadline with one goal and one goal only: put Tarik Skubal and Jacob Misiorowski together. They failed to accomplish that, and the Dustin May-sized consolation gift basket won’t do much when their main rival, the Dodgers, keep getting better and better as the days go on.
May is a player I struggle to understand, as teams continuously talk themselves into his upside before experiencing his many downsides. He had a couple of majestic starts for the ripping-hot St. Louis Cardinals early in the year before he snapped back to reality (ope, there goes gravity). Meanwhile, the Cubs seriously improved their pitching situation by adding two starters and Milwaukee is left with the sinking feeling that all National League teams feel: is there any hope against Los Angeles?
No team better identified their biggest need and aggressively addressed it than the Chicago Cubs did with starting pitching. Maybe they were in on Skubal or Freddy Peralta, but with those two off the board they quickly snatched up two elite rental options in Kevin Gausman and Clay Holmes. That is a substantial improvement to the 2026 team with mostly replaceable prospect commitments. The Cubs clearly understand they have something special with the 2026 ball club, and went out and improved it with proactive but low-risk moves. If Gausman and Holmes aren’t the best thing since deep-dish pizza? No problem, they’re not going to be around very long anyway.
This type of hybrid approach at the deadline is valuable because it doesn’t tilt the scales too hard in either direction. The Cubs have a good thing going, but also realize they have a chance to build a contender for years to come with their young stars. There’s no need to go supremely all-in when notable rental improvements keep some powder dry for later. I think the Cubs have positioned themselves well.
(pops Red Sox bias on the gramophone and reclines in old-timey chair) When the Yankees traded for first baseman Luis Garcia Jr., multiple successive tweets about the trade made sure to include that Garcia “LEADS THE NATIONAL LEAGUE IN SLUGGING PERCENTAGE” like people who forget about it if you didn’t persistently remind them. Garcia is, however, not some kind of All-Star-level hitter. He’s good, and can provide above-average offensive production, but he’s not the league-swinging savior.
Heliot Ramos is another good-not-great add, but the Yankees’ biggest failure was an inability to trade for a catcher to replace Austin Wells. Every single catcher in the universe was mock traded to the Yankees in the last few days, and they just couldn’t get a deal done. It’s possible the Yankees have medical information on Aaron Judge that suggests he will not be back this season, which would certainly explain their inaction. Otherwise, it’s hard to explain.
Cherry on top: when Yankees GM Brian Cashman was asked about their catcher pursuit, he responded that, for Adley Rutschman, “We were unable to meet the price, so they did their business elsewhere.” That somewhere is our next winner on this list.
(flips Red Sox bias to side B and reclines even further in old-timey chair) There are a lot of ways to take Boston trading Anthony Eyanson and several other prospects for Adley Rutschman: it’s an in-division blockbuster meant to give Orioles fans convulsions; a massive overpay with ultra-valuable prospects for a player who never lived up to the hype; a furious win-now move from Craig Breslow which revived his reputation with Red Sox fans.
Here’s my two cents: I am not a scout. I have never seen Anthony Eyanson pitch, nor do I have strong opinions about the projection of Kyson Witherspoon, though I do my best to defer to smart people (like the crew at soxprospects.com, shoutout) for this stuff. What I do know is that the Red Sox dramatically improved their catcher position and probably just added 5.0 WAR to their lineup overnight with a switch-hitting three-time All-Star catcher with a year and a half of control. And they added him to a team that has gone 25-5 in their last month of play in an American League that is dying for somebody to take it.
With additional moves like trading Marcelo Mayer for LHP Erik Miller making tons of sense for Boston, this was a deadline about winning in the playoffs right the heck now. Many may forget that Boston’s two best players, Roman Anthony and Garrett Crochet, have missed basically the entire season. If they (and Rutschman actually, he’s on the IL) can get healthy? Watch out.
