It’s Brian Cashman’s time to hit a home run for Yankees



The Yankees were good last season, good enough to win 94 games, tying them for most in the American League. They just weren’t good enough to beat the Blue Jays by a game, which would have given them a first-round bye. Eventually they got rolled by the Jays in the Division Series same as they got rolled during the regular season. So, a year after finally making it back to the World Series for the first time in 15 years, this time they couldn’t make it past baseball’s Elite Eight. Good. Just not good enough. Again. It’s who they are now.

Hal Steinbrenner — whatever happened to him, cat got his tongue? — and Brian Cashman occasionally get defensive because they clearly think they don’t get enough credit for their team having a chance year after year; for the Yankees having a winning record year after year, all the way back into the 1990s. Except for this: They’re the Yankees, and unless the bar has been set at being good even if it means never being good enough, they need to have a better understanding of how frustrated their fan base is.

Not spoiled. That’s a soft, tired narrative about fans who support this team the way they do. Year after year. Just frustrated watching the Dodgers win two World Series in a row, and three in six years, frustrated watching the Astros make seven American League Championship Series in a row and making it to three World Series between 2017 and 2023. Oh, sure. Yankee fans look at just those two teams and wonder what’s stopping their team — and their owner, and their general manager — from doing the same thing.

Cashman isn’t under the same pressure that his counterpart with the Mets, David Stearns, is under this offseason. Because despite the fact that Stearns’ owner, Steve Cohen, recruited Stearns out of Milwaukee as if recruiting the guy who invented baseball, Stearns doesn’t have a job for life at Citi Field. And very little capital with his own fans these days.

Cashman apparently does have a job for life, despite the fact that he has assembled just one World Series winner in the past 25 years. But the longer the Yankees go without winning the Series — and despite Cashman having become the longest tenured front-office guy in all of recorded history — the more this becomes about Cashman’s legacy with the Yankees, and with Yankee fans. And there ought to be plenty of urgency to that, because his legacy is now tethered to the legacy of Aaron Judge, one of the greatest Yankees who has ever lived, about to enter his 10th full-time season as a Yankee and still looking for his first World Series ring.

The other night Cashman once again participated in Covenant House’s Sleep Out at the Javits Center, something that is always a worthy and honorable cause for him. Before he did, he once again sounded like Sweet Dreams Cashman in assessing where the Yankees are entering another offseason, after another season of not being quite good enough.

“I think we’re in a good spot,” Cashman said. “The job right now is to find out what’s available, and those all have different price points.”

Of course he is very good at his job, or the Yankees wouldn’t have a chance almost every October. He just needs to be better at it, the way his team needs to be better next season. Maybe that will involve the Yankees doing something dramatic, swinging a big trade for Corey Seager or somebody else. For now, though, and just off the signals Cashman has given off, first in his closing media session at Yankee Stadium and then the other night at the Javits Center, it seems that the Yankees are more than willing to run the whole thing back again. Without major changes.

They have already brought back Trent Grisham for $22 million, and obviously in firm belief that the offensive numbers he put into the books last season weren’t flash-in-the-pan stuff. Cashman has also made no secret of wanting to bring back Cody Bellinger, the team’s second-most-MVP last year after Judge, on some kind of extended contract, though you wonder if by the end of it Bellinger might be on his way to DJ LeMahieu-ville. The expression you’re hearing around baseball is soft buys for Hal and Brian, rather than swinging from their heels the way other guys do for somebody like Kyle Schwarber, or even Pete Alonso. Or swinging a trade for somebody like Bryce Harper, whom they once loved and lost.

But Yankee fans I talk to would be fine with that if they could see evidence of the kind of down-roster grinders they just saw from the Dodgers and Blue Jays in the World Series. Both teams have their stars, too, you bet they do, the Dodgers especially. But the October spotlight also found guys like Ernie Clement and Kike Hernandez and Tommy Edman and Miguel Rojas, who became one of the home run heroes of Game 7 for the Dodgers.

There are other problems with the Yankees as currently constructed: They had a winning record against only three of the other 11 playoff teams: 5-1 against the Mariners, 3-0 against the Brewers, 2-1 against Padres, those last two series at Yankee Stadium. They had a losing record against all other playoff teams except their old friends the Guardians. And finally got good and boat-raced by the Blue Jays in that Division Series.

Their 2026 rotation, when everybody is finally healthy, looks loaded. It does. From here, and for now. But how can anybody be sure that Gerrit Cole, coming off Tommy John surgery, is going to be the same workhouse he was before, and at the age of 35? Until he is fully healthy and Carlos Rodon is fully healthy, they will be expecting much from Max Fried, who faded more than somewhat after a brilliant start to his season, and Cam Schlittler, a kid with a big arm who had such a big finish. We’ll see how he stands up across the long season.

Always with the Yankees — and not just the Yankees — you get the idea that the team that starts the season is just a first draft, and they will fix what needs to be fixed at the trade deadline. But perhaps this time can be different for Cashman. Perhaps this time he shows the kind of creativity over the next few months that is required to assemble a complete team finally ready to win it all. Make it through the “randomness” of the postseason and all the way back to the Canyon of Heroes for the first time since 2009.

And you know who seem to do pretty well with that “randomness?” The Dodgers do. So did the Astros until they fell down in the Wild Card series of 2024, and fell all the way out of the playoffs this time.

Are the Yankees in a good place entering this offseason? They are. They just need to get to a much better place next season. Need to be better, period. It starts with the general manager. Everybody on his team hits home runs. Now he needs to hit one.

TIME TO BUBBLE WRAP DART, HAPPY BIRTHDAY TO THE KING OF WOMEN’S SPORTS & HIT THE COUCH, CAM …

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