LAS VEGAS - The Yankees keep paying like a powerhouse, but the results keep looking like a team stuck in the same October loop. Another postseason flameout has stretched New York’s championship drought to 17 seasons, and Scott Boras used the general managers meetings Wednesday, Nov. 11, to put that reality in blunt terms.
Boras, who represents Gerrit Cole and Cody Bellinger, didn’t call for Aaron Boone or Brian Cashman to be shown the door. He went after the bigger question: whether the Yankees are actually getting what their money, their brand and their leadership should deliver.
“I can tell you that they’ve done a lot of right things, but on the other side of it is, I have to tell you, is that have they achieved what they want to achieve?” Boras said.
“And you know what? The group of people they have, the ownership they have, they should achieve what they want to achieve, and I’m sure that they have to look at that every day and say, ‘I have to do more, or I have to do different.’”
Then he cut straight to the heart of it.
“But the one thing I can’t do is I just can’t repeat what I’ve been doing,” Boras said.
That message lands hard in a Yankees offseason that already has plenty to fix. New York needs bullpen help with several relievers headed for free agency, has infield questions to sort out and still has to build an offense that doesn’t lean so heavily on Aaron Judge to keep everything afloat.
The organization, though, is staying the course at the top. Boone is set to return for 2027, and Cashman remains in charge of the roster. Boone is heading into his 10th season as manager, while Cashman has run baseball operations since 1998.
The Yankees won 93 games in 2026, then got swept out of the American League Division Series by Tampa Bay. The Rays closed the series with a 4-3 win at Yankee Stadium, and the drought rolled on.
Steinbrenner has kept backing his baseball operations leaders anyway. He also pointed to the offense as a major reason the season ended the way it did. New York’s search for upgrades includes second base, third base and a bullpen that Cashman has already called his biggest offseason priority.
Anthony Volpe is part of that infield conversation. After returning from Triple-A in September, he showed he could help at second and third base.
Boras has a direct tie to that turnaround: Volpe sought his advice during a difficult 2026 season, changed his approach in the minors and later joined Boras’ agency. He hit .265 over the closing stretch described in the reporting and returned to the postseason lineup.
Judge, meanwhile, made his own demand after the loss to Tampa Bay. The captain said another winning season and another playoff trip are not enough for a franchise that says it is chasing titles.
“We’re the Yankees,” Judge said. “I feel like they should go all in and do what they need to do and find. If we’ve got holes, if it’s finding certain players or personnel, whatever we need, you’ve got to go out there and get it.”
He pushed the point even further.
“They give us a winning team every single year, but that’s not good enough here in New York. We’re the Yankees. You’ve got to go out there and chase championships and go all in every year,” Judge said.
Boras’ comments echo that same frustration from a different angle. Both men are saying the same thing in different ways: the Yankees’ standard is higher than simply being competitive.
He also pointed to a changing league landscape. Smaller-market clubs now have more ways to compete, with outside investment and stronger development systems helping them challenge the old financial order. New York’s 2026 competitive-balance-tax payroll was roughly $336 million, third highest in MLB, yet the season still ended before the league championship series.
Tampa Bay knocked the Yankees out, and Milwaukee went on to win the World Series. Boras’ point was clear enough: money alone no longer guarantees the route to a title.
The timing makes the whole thing even messier. The collective bargaining agreement expires Dec. 1, and a lockout is expected as owners push for a salary cap while players resist it.
Boras is firmly against a cap. Steinbrenner, who sits on MLB’s labor policy committee, has said he supports the owners’ proposals, including a cap and salary floor.
So the Yankees are staring at a winter where the roster needs work, the labor climate is tense and the pressure to do something different is only getting louder. Cashman says he is operating under the budget Steinbrenner has given him. Boras’ warning is now hanging over every move that comes next.
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