MLB: Boston Red Sox at Atlanta Braves
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The New York Yankees have long been known as the Evil Empire around baseball, a nod to the way things were run as the team dominated Major League Baseball for decades. While things may not be the same anymore, they’re still run like a ruthless business, despite not winning a World Series since 2009, with just one appearance in the Fall Classic since that time.

That’s rubbed many players the wrong way, and recently, we learned of another player that was frustrated with their time in New York, and reportedly, he’s a trade target for the Yankees heading into the 2026 MLB trade deadline.

New York Yankees Reportedly Targeting Aroldis Chapman

MLB: Tampa Bay Rays at Boston Red Sox
IMAGN IMAGES via Reuters Connect

That would be Aroldis Chapman of the Boston Red Sox, who has been rumored to be on the move in recent times, and given that he’s had not one, but two stints in New York, they make sense as a logical landing spot as a genuine World Series threat in 2026.

However, it doesn’t seem as though things there ended on a positive note, as the 38-year-old veteran was recently asked about the possibility of heading back to the Bronx, and what would need to happen for him to be happy about the deal.

Aroldis Chapman Demands An Apology from Yankees GM Brian Cashman

While he played it as politically as he could, it was clear who Chapman was calling out, later confirming it was Cashman as he revealed he would need an apology before he would ever consider returning to the Yankees following his last stint there that lasted between 2017 and 2022.

“What happened, happened. If something like this were to happen, I believe someone from this organization should apologize first.

This all dates back to Chapman’s last season in New York back in 2022, as he was left off the playoff roster for an odd situation, as Chapman claims he had permission to go to Miami, with Cashman calling out the veteran reliever for insubordination. Clearly, this is a touchy situation that’s come to the surface once again, but with the Yankees needing a high-leverage lefty, Chapman would be the perfect pickup, as he’s posted a 0.46 ERA across 19.2 innings thus far in 2026.

Not only would this situation need to be resolved, but heated rivals the Yankees and Red Sox would need to come together to make a trade, so it appears to be unlikely given all of the hard feelings involved in this situation.