MLB trade deadline 2026: Biggest winners and losers

This year's MLB trade deadline is over, and, as is usually the case, the final hours before the 6 p.m. ET cutoff went down with a flurry of activity.

The biggest trade of this year's deadline came Saturday night, when the Detroit Tigers dealt star ace Tarik Skubal to the reigning champion Los Angeles Dodgers. Things heated up after that, with a few more big deals Sunday -- Freddy Peralta to the Tampa Bay Rays and Kevin Gausman to the Chicago Cubs, to name a few -- before Monday rolled around with all the action, including multiple intra-division swaps and a blockbuster trade. That was the Baltimore Orioles sending catcher Adley Rutschman to the Boston Red Sox for a haul of Boston's top prospects in one of the more surprising deals of this deadline. Other big movers Monday included Luis Arraez, Clay Holmes, Luke Weaver and more.

Who came out on top as the biggest winners of the deadline? And who were the biggest losers, leaving much to be desired? Let's dig in.

The big winner: Los Angeles Dodgers

The general reaction around the sport after the Dodgers acquired Skubal for Zyhir Hope, River Ryan and Brady Smith: That's all it took? Or: No, not the Dodgers! With many additional exclamation points.

Hope and Ryan are certainly good prospects, ranking fifth and the eighth in a talented Dodgers system before the trade, but Hope was the third-best outfielder on his team at Double-A Tulsa and Ryan has pitched so sparingly the past few years -- only 36 innings this season in Triple-A, as he hasn't pitched since June 17. Smith is, believe it not, 0-10 in his minor league career (OK, also with 113 strikeouts in 74 innings this year between Single-A and High-A).

Still, this is like a pinprick to the Dodgers, acquiring arguably the best pitcher on the planet without doing much damage to the farm system. Skubal was the clear difference-maker at this trade deadline and has pitched well since returning from his early-season elbow surgery. He gives the Dodgers a potential No. 1 starter to open the playoffs while providing insurance against the current injuries to Shohei Ohtani (a sore knee that is preventing him from pitching), Blake Snell (rehabbing in the minors) and Tyler Glasnow (expected to begin his minor league rehab Tuesday).

Importantly, the trade also means the Dodgers won't have to face Skubal in the playoffs -- oh, and it gives them an inside track to re-signing him when he hits free agency after this season.

If everyone is healthy in October, the Dodgers can dream of a playoff rotation featuring Skubal, Yoshinobu Yamamato, Ohtani and either Snell, Glasnow or Justin Wrobleski. Look, is it obnoxious that they pulled off this kind of move once again? Of course it is. The World Series favorites just got better.

The hope for other teams now rests on the idea that at least Skubal hasn't been quite as dominant as he was before the surgery, including a slight drop in velocity (and, actually, the Mariners beat the Tigers in both games Skubal started in last year's American League Division Series). Or that the Dodgers' offense also hasn't been quite as strong as recent seasons. Or, simply, that anything can still happen in the playoffs.

Winner ... and loser: Baltimore Orioles

In less than three years, the Orioles went from 101 wins and what many believed might be a potential American League dynasty to dumping at the trade deadline. They traded Rutschman to the Boston Red Sox and Taylor Ward to the Seattle Mariners, among a few other deals, essentially waving the white flag on their 2026 season. But they received a massive haul from the Red Sox, with three of Boston's top five prospects for a player with only one-plus seasons remaining of team control. Given Rutschman's inability to stay healthy and numbers that fail to match his reputation, it's hard to argue that trade from a baseball standpoint. The Orioles did enter Monday with about a 17% chance of making the playoffs, via FanGraphs, but this never felt like a playoff team.

Still, it's always a gut punch when a team within shouting distance of a playoff spot decides to trade key players rather than adding, and more painful in a season in which the AL is so wide open. But more than anything, it's symbolic of everything the Orioles have done wrong since that 2023 season, and all the once-promising prospects and players who never quite developed as expected.

The Orioles have a replacement for Rutschman in Samuel Basallo, and they received two nice pitching prospects in the Boston trade -- so maybe, once again, the future looks bright. But does anyone believe the Orioles will take the extra steps to win when that day arrives?

The big loser: Milwaukee Brewers

Should Brewers fans be mad at the Dodgers, who are simply playing within the rules of the system? Or should they be angry at their own team for not pushing its chips to the table? If any team would have been able to outbid the Dodgers for Skubal, it would have been the Brewers, who could have kept top prospect Jesus Made and still had plenty of talent to offer from a loaded farm system.

This absolutely should have been the season the Brewers went all-in trying to claim the first World Series title in franchise history. Imagine facing Skubal and Jacob Misiorowski a combined three times in a best-of-five series or four times in a best-of-seven. Factor in that nobody knows what Misiorowski's future holds and whether he can remain healthy throwing 100-mph pitch after pitch after pitch, and it just felt as if this was the time for the normally cautious Brewers to be a little adventurous and risk long-term value for a short-term push to maximize their World Series chances.

It could be that the Tigers demanded Made or Luis Pena and the Brewers said no way. Or that the Brewers didn't want to part with Logan Henderson, who has a 2.66 ERA in nine starts (lower than Skubal's 2.79 ERA, by the way). Milwaukee did end up adding a starting pitcher, Dustin May, in a deal with the St. Louis Cardinals on Monday, but that's no Skubal-Miz 1-2 punch.

It's possible the Dodgers and Brewers meet again in the National League Championship Series -- where Milwaukee was swept by L.A. last October after boasting the best regular-season record -- but now, beating the Dodgers will be even more difficult.

The other big loser: Detroit Tigers

There's little doubt that blowing a 7-0 lead last Wednesday to the Orioles -- with Skubal on the mound -- cemented Detroit president of baseball operations Scott Harris' decision to trade his ace. It was fair to watch that game and think, "This team isn't a playoff team, let alone a World Series team, so let's trade Skubal for future assets."

It's also fair to criticize an organization that just traded its best player on a Saturday night that saw them end the day just 2 games out of a wild-card spot. Keep in mind that since MLB expanded to six playoff teams in 2022, we've seen the 2022 Phillies, the 2023 Diamondbacks and the 2023 Rangers reach the World Series as wild cards, with the Rangers winning it all. Given the overall weakness of the American League, just getting into the playoffs gives a team a reasonable shot at the World Series. Via FanGraphs, the Tigers had a 20% chance of making the playoffs entering Sunday.

They took that 20% and threw it back in the face of their fans, who haven't seen the Tigers in a World Series since 2012 and haven't seen them win the trophy since 1984. Look, it could still work out for them. They traded Jack Flaherty and several others at the deadline in 2024 and then had a miracle run the rest of the way to reach the playoffs. Maybe River Ryan joins the rotation and goes 6-0 down the stretch and Zyhir Hope wins back-to-back MVP awards in 2031 and 2032. But for now, trading Skubal to the Dodgers is a choice the Tigers made to make themselves worse the final two months -- and made the best team in baseball even better.

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