Hilarious Aroldis Chapman 'Yankees demand' emphasizes so much regret

Sometimes you just have to laugh at the irony of baseball. The New York Yankees will head into the trade deadline hunting high-leverage relief help, and the best chip on the market to scratch that itch is expected to be former Yankee and current Boston Red Sox closer Aroldis Chapman. Could a reunion for a third stint in the Bronx be in line for the Cuban Missile? Don't bet on it. Chapman has made it clear that if traded back to New York, Brian Cashman would have to apologize to him first.

"What happened, happened," Chapman said, per ESPN. "If something like this were to happen, I believe someone from this organization should apologize first."

It's a stunning lack of self-awareness from Chapman, who, if you recall, was left off the 2022 ALDS roster not because he pitched abysmally with a 4.46 ERA and subtracted 0.2 fWAR from the club, nor because of the time he missed due to an infected tattoo, but instead, because he decided to go AWOL and miss a mandatory team workout.

Years later, it's still on his mind, though. As we saw from his October 2025 comments, he clearly sees reality through a distorted lens if he thinks being held accountable for his own actions is some form of disrespect.

The lefty entered 2026 coming off the best season of his career, in which, at the tender age of 37, he finally learned that one of the main objectives of pitching is to throw strikes. This year, he's been even better with a 0.46 ERA over 19 2/3 innings, though his walk rate has spiked back up from 6.6% to 11.7%, foreshadowing an inevitable crash.

Needless to say, the Yankees won't be trading for Chapman this year (or any other year in the future), but the bigger issue here is that this is a reminder of how much time and resources the club wasted on him in the first place.

Aroldis Chapman's latest insane comments are a reminder of wasted Yankees moves

The first red flag that the Yankees missed and shouldn't have ignored was Chapman's domestic violence incident when they traded for him in December of 2015. This wasn't simply an instance of a heated misunderstanding, as Chapman was suspended for allegedly choking his then-girlfriend and taking out a pistol and firing eight shots in his garage.

That was a situation that could have had an (even more) ugly outcome, and, frankly, the league let him off easy. New York overlooking that incident because of his talent (and decreased trade cost) is a stain on the franchise. It was, however, one that they could have escaped from relatively easily.

The 2016 club bottomed out, and Chapman was dealt to the Chicago Cubs for a haul that was headlined by a then-19-year-old Gleyber Torres. That should have been the end of it, but Cashman decided to get cute and re-signed Chapman as a free agent the following winter.

The five-year, $86 million deal the Yankees gave him in 2017 still stands as one of the largest contracts ever handed out to a reliever nearly a decade later. New York got very little for that money because, although Chapman put up good regular-season campaigns (and some not-so-solid ones), he had a habit of melting down when things mattered the most. But don't you worry! They didn't learn, and extended him again years later when he threatened to opt out of that original historic deal.

The back-breaking postseason homers, such as the 2019 Game 6 blast he allowed to Jose Altuve to bounce the Yankees in the ALCS, or the dinger he gave up to Mike Brosseau of the Tampa Bay Rays in the eighth inning of Game 5 of the ALDS, which ended the Yankees' season the following year, sum up the Chapman experience.

The fortunate thing for us is that a blizzard in July is more likely than Cashman apologizing to Chapman, so we no longer have to fear him withering during the biggest moments. But with that, we still carry the scars of an experience that went on for far too long, and probably never should have happened in the first place.

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