Yankees should deal for two of their Astros torturers, according to a New York insider.

In a technical sense, that is. In theory.
Suddenly, there’s a more compelling reason for the New York Yankees to support the Houston Astros to miss the playoffs than just jealousy.

Despite their early season collapse, the ‘Stros are back to within.500 and should be confident this summer, as they have reachable Wild Card places right in front of them with only the Mariners standing in their way in the AL West. Given their history of racing straight to the ALCS, it’s hard to argue with FanGraphs’ assessment that the Astros have a roughly 50% chance of making the postseason. Houston will most likely be “going for it” again this year, barring another outstanding fall, but that doesn’t mean the Yankees can’t dream.

The Bombers have raced to the top of the AL East, but are lacking proven swing-and-miss arms in the bullpen. Their infield is also spotty at best; whether Anthony Rizzo is healthy or not, Anthony Volpe represents the only name fans can unequivocally trust right now. That means that, yes, third base is very much open.

Joel Sherman of the New York Post is well aware that the Yankees and Astros probably won’t link up this summer, but he couldn’t help but be tempted by the idea of a Ryan Pressly/Alex Bregman package, which would send one of the game’s preeminent Derek Jeter fans to the hot corner in the Bronx.

Could the Yankees try to acquire Ryan Pressly and Alex Bregman from the Astros? No, but…?
The Yankees have a clear need at the position, but Bregman, a free agent after the 2024 year, surely won’t be in their sights. Hal Steinbrenner and Brian Cashman will be too preoccupied budgeting for Juan Soto; they are unlikely to use their money on a $150–200 million Bregman contract unless New York goes supernova. The Yankees in 2004 would have succeeded. The Yankees of 2024? You already have their word that they won’t.

Still, the Astros probably won’t extend Bregman, either. They’re saving space for Kyle Tucker, and have already deftly reloaded and replaced key figures like George Springer and Carlos Correa in recent years. In that case, why not get a head start, given the semi-sorry state of their farm system? They could parlay Bregman’s recent hot streak (a .366 average/1.040 OPS over the past 28 games) into an overpay, and the Yankees could entice them with lottery tickets like Roderick Arias or (gulp) Spencer Jones. Pressly, dealing with a down year, would come cheaper, though his 38 Ks in 30 innings (4.50 ERA, 1.467 WHIP) still represents more swing-and-miss than most Yankees relievers.

The Astros are likelier to say no to these conversations than the Yankees, who’ve been more than willing to overlook rivalry walls in past trade chatter. But still, for the time being, it’s fun to think about how an Astros plummet could be mutually beneficial.