Brian Cashman Opens Up at Winter Meetings, Revisits Sonny Gray Saga and Yankees' Lineup Imbalance
It’s been a while since Sonny Gray wore pinstripes, but his name resurfaced in a big way during Day 1 of the MLB Winter Meetings - and not because of a trade or a throwback highlight. Yankees GM Brian Cashman used his media availability to revisit Gray’s turbulent time in New York, shedding new light on the pitcher’s mindset during his short-lived Bronx stint and sparking fresh debate about how it all went down.
According to Cashman, Gray privately admitted back in 2018 - after the trade deadline had passed - that he never wanted to be a Yankee in the first place. The conversation reportedly came after Gray had struggled on the mound and expected to be moved. When the trade didn’t happen, Cashman says Gray opened up, revealing that his heart was never in New York.
That revelation lines up with Gray’s own recent comments during his introductory press conference with the Red Sox, where he said he “never wanted” to join the Yankees. But what’s raised eyebrows is the timing - and the contrast between Gray’s public enthusiasm when he was first traded to New York in 2017 and his more recent honesty. Yankees fans, never ones to forget, have already called out what they see as a contradiction.
But the story doesn’t end there. Cashman added another layer to the drama, saying that Gray told him he only expressed interest in joining the Yankees because his agent, Bo McKinnis, advised him to.
The logic? Saying he didn’t want to go to certain teams wouldn’t help his market value.
“[McKinnis] told me to lie,” Cashman recalled Gray saying. “Because it wouldn’t be good for my free agency to say there’s certain places that I don’t want to go to.”
That’s a bombshell - not just because it paints Gray’s early enthusiasm as a PR move, but because it suggests the agent was pulling strings behind the scenes to keep his client’s options open. It also adds a bit of nuance to the entire situation.
If Gray was just following his agent’s advice, does that soften the blow for Yankees fans? Or does it make the whole episode feel even more disingenuous?
McKinnis, for his part, didn’t sit quietly. He fired back, questioning the logic of Cashman’s version of events and denying that Gray ever said he wanted out of Oakland in the first place.
“This makes zero sense,” McKinnis said. “The words, ‘I want out of Oakland,’ have never been said by Sonny.
He loved his time with the A’s.”
So, we’ve got a GM airing out a five-year-old conversation, a pitcher who’s moved on to a new team, and an agent pushing back hard against the narrative. It’s the kind of unexpected offseason drama that only baseball can deliver - part confessional, part feud, and fully captivating.
But Cashman didn’t stop there. In the same media session, he turned the spotlight on the current Yankees roster, acknowledging a very real concern heading into 2026: the lineup is too left-handed.
“We are too left-handed right now, without a doubt,” Cashman said, per MLB.com’s Bryan Hoch.
That comment didn’t go unnoticed. Fans were quick to point out the irony - especially since the Yankees have reportedly offered a qualifying offer to lefty Trent Grisham and continue to stay in touch with Scott Boras about another lefty bat, Cody Bellinger. Social media lit up with trade proposals and mock lineups featuring right-handed hitters like Fernando Tatis Jr. and Ketel Marte - not because there’s any real traction, but because fans are reading between the lines and dreaming big.
Cashman’s candor was refreshing, if not a little surprising. In a sport where front-office execs often speak in vague generalities, he came out firing - revisiting old wounds, calling out roster imbalances, and giving fans a rare peek behind the curtain.
Whether you agree with how he handled the Gray situation or not, one thing’s clear: Cashman wasn’t holding back. If Day 1 of the Winter Meetings was any indication, the Yankees’ offseason could be as unpredictable as ever. And if Cashman keeps this energy going, fans might want to keep their popcorn close by - things could get even more interesting.