The Yankees fans might be clowning the Mets fans as their “Little Brother” for taking their cast-offs, but at least they are doing something. But until now, the New York Yankees have not done any signing that could give the fans confidence going into 2026. And now, Brian Cashman has been given an ultimatum.

The ultimatum given by Chad Jennings of The Athletic is to either step up and go big at least now, or things in the 2026 season are going to get ugly.

“The Yankees are notoriously aggressive and have made a splash each of the past three offseasons,” wrote Jennings. “Now, they’ve lost Cody Bellinger to free agency, and there are question marks all over their pitching staff. They have to do something big at some point, right?”

New York finished 2025 with an ALDS exit against Toronto, exposing roster gaps entering winter. After that loss, Brian Cashman said the Yankees would address weaknesses aggressively this offseason. Instead, early moves have centered on re-signings, signaling caution rather than structural roster change yet.

That disconnect between promise and action has defined how fans experienced the opening months thereafter.

The most significant deal was Trent Grisham accepting a $22.025 million qualifying offer for 2026. Grisham produced a .235 average, .348 on-base percentage, .464 slugging, and 34 home runs total. New York also retained Ryan Yarbrough for one year for bullpen and rotation coverage depth. Those moves add stability, but they do not replace departed impact talent from last season.

The pitching staff still carries risk, with Gerrit Cole and Carlos Rodon returning midseason from injury. Beyond internal hopes, the Yankees have not added external starters despite known workload concerns leaguewide. Aaron Boone’s public comments have emphasized patience, offering little clarity about specific pitching solutions ahead.

As spring approaches, the uncertainty in the rotation still shows looms large and looks no different from last season’s end.

Offensively, the Yankees lost market ground as top bats moved, including projected stars elsewhere early. Cody Bellinger’s projected $182 million contract and Kyle Tucker’s projected $420 million contract costs placed both beyond reach financially. Without meaningful additions, New York risks entering 2026 behind Baltimore, Toronto, and Boston in the standings.

If this winter closes quietly, the Yankees face an AL East unusually unforgiving by design.

At some point, patience turns into permission, and Brian Cashman is nearing that line. Aaron Boone keeps selling calm while rivals spend loudly, and the contrast keeps growing. If this offseason ends quietly, 2026 will deliver answers the New York Yankees cannot spin away.

Some moves that could prove that Brian Cashman didn’t mess up the Yankees’ offseason

For a front office that never misses a chance to remind everyone how complicated roster building is, the silence has been loud. Brian Cashman knows how this works in New York. Optics matter, urgency matters, and patience only sells when it produces results. A few decisive moves would quickly change the tone around the Yankees.

One path involves signing Cody Bellinger, projected at 7 years and 182 million dollars total. Bellinger produced 25 home runs, 88 RBIs, and a 121 OPS+ last season with consistency. Those numbers explain why his left-handed bat remains valuable in Yankee Stadium. Such a signing would immediately stabilize the outfield while clarifying the long-term payroll planning outlook.

Attention then shifts toward Bo Bichette, projected to command 10 years and 300 million dollars. Bichette hit 29 home runs, posted a 128 OPS+, and accumulated 4.5 WAR during the season. His right-handed production would balance a left-heavy order without forcing defensive compromises elsewhere. That path also weakens Toronto while giving New York a controllable middle infield solution long-term.

Top Stories

Bo Bichette’s Toronto Future Fades Fast Amid Yankees Buzz as Ross Atkins Moves to Block Pirates, Per Insider

Blue Jays Line Up Kyle Tucker Alternative As Dodgers’ Sudden Splash Shakes Offseason Plans: Report

Phillies Veteran Warns Dave Dombrowski as $100M Star’s Exit Confirmed After Rob Thomson Fallout

Who Is Adrian Beltre’s Wife, Sandra Beltre?

Mets Become Leading Contender For 30YO Ex-Phillies Star after David Stearns’ Mega Offseason Misses, Per Insider

Pitching remains central, with Sandy Alcantara carrying a 3.32 career ERA across 858 innings pitched. Alcantara is owed 17.3 million dollars annually through 2026 under his existing contract with control. The bullpen option includes Pete Fairbanks, who recorded 25 saves and a 2.58 ERA last season. Fairbanks is projected to be near 4 years and 60 million dollars, sealing late innings for the Yankees.

Put together, these moves outline how Brian Cashman could turn silence into measurable intent. The Yankees rarely need explanations, only transactions that force the room to stop questioning. If those numbers arrive, Cashman is not defending patience; he is redefining accountability publicly.