ORLANDO, Fla. — Before Yankees general manager Brian Cashman headed to the airport Wednesday after four uneventful days at the Winter Meetings, he spent 15 minutes discussing his week with beat writers next to the Waldorf Astoria Orlando pool.
Angry Yankees fans will say the setting was fitting. They’ll say Cashman is drowning his way through the baseball offseason.
“I haven’t accomplished anything,” Cashman admitted.
Since losing the AL East title in a tiebreaker and then being eliminated in a Division Series – the AL champion Blue Jays did the honors in both – the Yankees picked up reliever Tim Hill’s club option, overpaid to keep center fielder Trent Grisham for another year and brought back versatile lefty Ryan Yarbrough for 2026.
Those moves, however, didn’t dent the Yankees’ offseason wish list, which starts with re-signing outfielder Cody Bellinger and includes adding high-leverage relievers, a right-handed-hitting catcher, right-handed hitters for the bench and maybe making a big trade to balance out of the leaning-left lineup.
“We’re just staying engaged, trying to match up with some things, but it’s been tough so far,” Cashman said. “Don’t like the asks coming our way, and the opposing teams, with what I’m trying to pull from them on the trade stuff, they’re not liking currently anything.
“We do have some conversations that possibly could lead somewhere, but clearly, obviously, if we had something, we would have done it.”
Cashman had a meeting set up for late Wednesday morning with an agent or fellow GM to discuss a free agent or trade, but expected to return to New York for the holidays striking out at the Winter Meetings.
Cashman is disappointed, but most of the players that he’s interested in adding through a signing or deal still are available.
The Yankees need relievers, but they didn’t make an offer to bring back Devin Williams, who signed with the Mets, or Edwin Diaz, who went to the Dodgers. Cashman wasn’t in on the lone big free agents who signed this week, pitcher Dylan Cease to the Blue Jays and designated hitter Kyle Schwarber back with the Phillies.
“There’s not a lot of the inventory that I’m interested in coming off the board yet, so that means it’s tough to get,” Cashman said. “So my experiences, I would assume, are the same experiences in other camps. But you keep working at it.”
As for Bellinger, the Yankees are waiting for agent Scott Boras to get serious about finalizing a deal with one of the supposed eight teams in contention.
“Markets, on a year in and year out basis, all behave differently, so I couldn’t speak to the side that has all the cards,” Cashman said. “Listen, Scott Boras has a very deep roster of players he’s looking to place and how and when he strategically decides to do that. We just stay in touch with the marketplace and see where that takes him, and therefore, us. (Bellinger’s) still on the board, as are others.
“And so, we’ll just stay engaged on those and see what happens.”
A reason for the slow December industry-wide, Cashman suggested, is clubs no longer begin working on offseason moves during the World Series and GM Meetings, which usually are held in the first week or November.
“I’m in a position as a long-time, long-tooth general manager, so I feel like the calendars are way different,” Cashman said. “I feel like the GM Meetings now should be strategically moved to the Winter Meeting times, and the Winter Meetings should be moved into January because I feel like everybody industry wise is in HR mode in November still with hiring managers and coaches and setting up their new front offices if somebody did a regime change.
“And so front offices are in setup mode and HR mode and not into player-acquisition mode. I feel like there’s a long delay getting out of the gates when you get a world champion crowned. There’s a long delay of actually getting to the player acquisition side via free agency or trade. So I feel like you’re running into mid-December when it starts now and into January, sometimes into February, where teams used to hit the ground running.
“Everybody used to go to the World Series, all the teams, and you’d have trade discussions at the World Series and then you’d be potentially culminating things in the GM Meetings.
“None of that stuff happens. Teams don’t go to the World Series anymore. And in the GM Meetings people aren’t really ready yet. So it feels like the goal post to the calendar moved way back and it’s a different world we’re living in right now in terms of that.
“So how do you fix it? I don’t know. And is it a problem? It seems like it.”
