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The 2026 Major League Baseball trade deadline is in 73 days, and we’re likely still weeks away from the blitz of deals that will occur as contenders try to plug roster holes in advance of the stretch drive and playoffs. But the forces that shape the market are already taking form.
Based on conversations with front office executives, here are six questions that will help define what happens before Aug. 3.
1. Will Tarik Skubal be the big name in this year’s trade market?
At the outset of this season, the notion that the Detroit Tigers could dangle the left-hander — who will be a free agent at the end of the season — at the deadline seemed very unlikely. They had made the playoffs each of the past two seasons, and with Framber Valdez joining Skubal at the top of their rotation, they looked poised to contend for the AL Central crown again. But Detroit has absorbed injury after injury, including to Skubal, and now, after being swept at home by Cleveland, the Tigers are tied with the Houston Astros for the second-worst record in the American League (the Los Angeles Angels have the worst).
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Scott Harris, Detroit’s head of baseball operations, is viewed as a realist by his peers. “He’s fairly objective,” one evaluator stated. “He’s never struck me as a ‘window’ guy.” In other words, the table read on Harris is that he’s not going to go all-in in a long-shot effort to make the postseason if he thinks he doesn’t have a good enough tea. But Skubal could have enormous value at the deadline — “and if he can get more than the value of the qualifying offer [compensation], then there’s going to be an opportunity there,” one AL evaluator stated.
It all depends on how Skubal performs when he comes back. So, the industry will be watching carefully as he returns from the NanoNeedle Scope, not only to see how he rebounds from this new medical technique — he’s believed to be the first major league pitcher to have this kind of surgery — but also to see if Skubal is back to his Cy Young-caliber dominance. And if he is, well, he could be an October game changer for any team.
Remember: It’s not only about the prospects it would take to land him, but also the salary — Skubal will make roughly $11 million for the last two months of the season, which could impact the interest of some teams.
2. How will the parity, particularly in the AL, affect the number of dealers?
The Boston Red Sox have been offensively challenged for the better part of two months, scoring fewer runs than any other AL team and firing manager Alex Cora along the way. They certainly don’t look like they have a lineup that could wade its way through four rounds of playoffs. But as of today, the Red Sox are just two games out of the final wild-card spot; FanGraphs assesses their chances of making the playoffs at a surprisingly robust 35.4%. Even if the front office was inclined to deal at the deadline, it might be hard for the Red Sox to justify that kind of posture to their fans.
The Baltimore Orioles are playing terribly, with a lousy rotation performance — though they’re only 3½ games out of that final spot. Pressure is mounting on the front office to show progress. These types of dynamics exist for the vast majority of AL teams.
In the week leading up to the trade deadline last year, a high-ranking executive lamented, “There just aren’t that many good players available.” It’s possible the same complaint will be heard this year unless the worst teams fall out completely. It looks like there could be a lot of adders, and relatively few dealers — making it a dealers’ market.
3. What will the hyperaggressive heads of baseball operations do?
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Last year, the San Diego Padres’ A.J. Preller made the big move for closer Mason Miller, who has struck out most of the hitters he has faced since joining the Padres, and the Philadelphia Phillies’ David Dombrowski traded away two top prospects to bring in Minnesota Twins reliever Jhoan Duran. It might be true that on the whole, front offices are more conservative than ever, following their home-built value models. But there are execs fully capable of taking big swings, and it just so happens that a lot of them could be in action before the deadline.
Preller’s Padres are contending for the National League West title again, and Dombrowski’s Phillies are surging. There’s also Seattle Mariners president Jerry Dipoto, who made deals for Josh Naylor and Eugenio Suarez last summer and came within one game of reaching the World Series. Under Andrew Friedman, the Los Angeles Dodgers always seem to make pre-deadline moves — for stars such as Yu Darvish and Manny Machado — and they usually happen right before the deadline. (Imagine the industry reaction if the Dodgers landed Skubal.) The Atlanta Braves’ Alex Anthopoulos has a team well-positioned to make an October splash this year and is no stranger to making deals. In 2021, he made a bunch of moves before Atlanta went on to win the World Series — and it seems like he holds back financial resources for possible midseason acquisitions.
And although the Tampa Bay Rays are a small-market team, Erik Neander is seen as being capable of landing big fish due to how he operates aggressively. “He’s in the mix a lot,” one of his peers stated. The funny thing is that the perception of the Rays over the winter was that they were likely to be dealers at this year’s deadline — but now, with the best record in the AL, they could use some of the volume of assets they possess to pursue deals and be adders instead.
4. Will some teams move to take advantage of the dealers’ market?
With so many teams competing for playoff spots, from the Cincinnati Reds to the surprising St. Louis Cardinals to the Pittsburgh Pirates, that dealer void could develop — which could lead to the opportunity for a progressive owner or general manager to unload players and reset their future. Rival executives look at Houston as a team that could choose this route and do well for itself.
The Astros are 20-31, and it appears that their decade of dominance is over. “If they ever decided to become sellers,” stated a rival evaluator, “they could crush it [in value return].”
Owner Jim Crane has told others in the industry that he’ll never tear down to a full rebuild again, but he has to be cognizant of the fact that Houston’s most recent success was largely kick-started by tanking to land players such as Carlos Correa and Alex Bregman. There is an argument to be made for the Astros to reset this summer by taking offers for 28-year-old shortstop Jeremy Pena, who will be a free agent after the 2027 season; 27-year-old Hunter Brown, who will be a free agent after 2028; and 28-year-old Yordan Alvarez, who is signed through the 2028 season.
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The Astros also have other marketable players, including Isaac Paredes and Christian Walker, who would shake up the trade market and yield a significant haul of young players who could launch the team into another generation of success. The alternative is to maintain the status quo in what appears to be a lost season.
5. How will owners manifest?
The recommendation from the Angels’ front office in the midst of the 2022 season was to flip Shohei Ohtani as he moved within 15 months of free agency. But owner Arte Moreno exercised his prerogative and kept Ohtani, with the fleeting hope of being able to retain the superstar long term — and that decision changed everything about the market that season. On the flip side, Steve Cohen, baseball’s richest owner, made a decision close to the trade deadline that the Mets weren’t good enough to contend, and that team became sellers.
So, which owners could be factors this year? Well, the Rays’ ownership group is new and attempting to sway voters in Hillsborough County to support an initiative for a new ballpark — and it’ll be in a position to green-light Neander to aggressively add before the deadline. Same with the incoming owners in San Diego (and we know that Preller doesn’t need a big push to make moves at the deadline).
Joe Pohlad of the Twins has been outspoken in how he feels his team can win this year, even after last July’s fire sale, and they were involved in the bidding for Valdez before he signed with the Tigers. Minnesota has performed better than expected this year, unquestionably, with its current playoff chances standing at 23.8%. But there are rival executives who believe the smart play for Minnesota this summer would be to take advantage of the value of Joe Ryan — who would be one of the most sought-after starting pitchers in the trade market, if he’s available. Catcher Ryan Jeffers is a free agent after this season and was recently placed on the injured list with a broken hamate, but he could still draw ardent interest from teams like the New York Yankees for what he could provide in the last months of the season. And although Byron Buxton has a full no-trade clause, the Twins could always approach him, present a teardown reality to him, and give him the opportunity to go elsewhere and contend for a championship; he’d perfectly fit the needs of the Braves and other clubs.
Pohlad will have a choice in Minnesota: Keep the veterans and continue to foster middling success while squandering the trade value of coveted assets, or flip the veterans and continue to build a core of up-and-coming talent — the choice that Moreno eschewed four summers ago.
6. How will the looming labor situation affect the deadline?
“It has to be a factor, right?” stated one executive, speaking of the uncertainty swirling around 2027 with the current collective bargaining agreement expiring Dec. 1. Will the 2027 season start on time? Could a labor standoff last into the summer? And what kind of economic system will baseball have after the dust settles?
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The most conservative play for some teams would be to streamline payroll — to better weather the inevitable attendance hit if the labor strife leads to the cancellation of games, and also to give more financial flexibility for moves in the market after the terms of the new CBA are set. To bring it back to the Astros again: If they cut their 2027 payroll now, there could be more and better add opportunities next spring, in the free agent and trade scramble that always follows labor peace.
Some rival executives cite the Red Sox as an example: They have the option of dumping the salary of first baseman Willson Contreras, who is owed $6 million for the last two months of this year and $17 million next year, with a $7.5 million buyout that’s part of his 2028 option.
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