Adam Ottavino Pulls Back the Curtain on Brian Cashman’s No-Nonsense Leadership - and Sonny Gray’s Departure
Adam Ottavino has pitched in some of the biggest markets in baseball, but even he was taken aback by the blunt honesty he encountered in his first days with the Yankees. On a recent episode of Baseball Isn’t Boring, the veteran reliever shared a behind-the-scenes moment that offers a rare glimpse into how Yankees GM Brian Cashman sets the tone in the clubhouse - and how that tone may have played into the departure of starter Sonny Gray.
Ottavino, who joined the Yankees ahead of the 2019 season, recalled a spring training meeting where Cashman didn’t mince words with the roster. The message? If you’re not fully committed to being a Yankee, speak up - and you’ll be moved.
“I was in the room for Cashman giving a pretty hilarious speech in spring training about, ‘If you don’t want to be here, I need to know so I can relocate you,’” Ottavino said, laughing as he recounted the moment.
At the time, Ottavino had only been with the team for three days, but the message stuck. Looking back, he suspects that Cashman’s pointed comments may have been referencing Sonny Gray, who had been traded away that offseason.
“Either way, it was a good message,” Ottavino added. “It was like, ‘Hey, we’re trying to win here.
We need everybody to be all in. If we’re not all in, that’s fine.
Come tell me, and I’ll fix it.’”
It’s classic Cashman - direct, no fluff, and all business. Ottavino didn’t have firsthand insight into the dynamic between Cashman and Gray, but the implication was clear: the Yankees expect full buy-in, and if that’s not there, they’ll find someone else who’s ready.
As for Gray, he’s found plenty of success since leaving the Bronx - and he hasn’t been shy about expressing how he feels about his time there.
In his introductory press conference with Red Sox media, Gray didn’t hold back, saying, “It feels good to me to go to a place now where, you know what, it’s easy to hate the Yankees, right?”
That jab adds another layer to Gray’s complicated history with New York. This isn’t the first time he’s voiced his discomfort with the Yankees experience. After being traded to the Reds in 2019, Gray openly admitted that “New York wasn’t a good fit” for him.
And the numbers tell a story of their own. During his time in pinstripes, Gray posted a 15-16 record with a 4.51 ERA over 41 appearances (34 starts). Not exactly the ace-level production the Yankees hoped for when they acquired him.
But since leaving, Gray has been a different pitcher. He’s gone 66-50 with a 3.51 ERA over 184 starts, earning two All-Star selections and finishing second in AL Cy Young voting in 2023. That’s not just a bounce-back - that’s a full-on resurgence.
In the end, Ottavino’s story sheds light on the culture the Yankees try to cultivate: one built on accountability, clarity, and a shared goal of winning. It’s not for everyone - and that’s exactly the point.