The New York Yankees aren’t a team built for patience, and this winter will be no exception. After another disappointing postseason exit, Brian Cashman made it clear he’s not planning to sit back while the rest of the league reshapes their rosters.
New York understands where it stands — in the thick of Aaron Judge’s prime, but possibly nearing the tail end of it. That reality puts pressure on the front office to deliver now, not later. Every move has to count, and the Yankees are well aware that standing still isn’t an option.
Cashman makes his intentions clear
Speaking with The Athletic, Cashman didn’t sugarcoat the team’s mindset heading into free agency. “We hope our strengths remain our strengths,” he said, “and we’ll go to town to improve upon our weaknesses.”
That’s as direct as it gets from the longtime general manager. The Yankees know where the holes are — and there are several. Despite investing heavily in starting pitching last offseason by landing Max Fried, they’ll open 2026 with uncertainty. Gerrit Cole is still recovering from Tommy John surgery, though he’s begun throwing again and is expected to return sometime next season. Carlos Rodón, meanwhile, will miss the early portion of the year after his own surgery.
Those injuries leave the rotation thin, and Cashman will likely explore both free-agent and trade options to shore up the group. Depth isn’t a luxury anymore — it’s a necessity.
Outfield questions loom large
The Yankees’ outfield is another focal point. Cody Bellinger’s free agency presents a major decision. His defensive versatility and steady bat made him one of the most valuable pieces on the roster in 2025, but re-signing him won’t come cheap. If the Yankees choose not to retain him, a pursuit of Kyle Tucker could be on the horizon — though that would require a long-term commitment likely north of $400 million.
Either way, the team needs another impact bat. The Yankees’ offense has leaned too heavily on Judge for far too long, and without protection around him, even the league’s best player can’t carry the lineup forever.
The Volpe question
Then there’s Anthony Volpe. Once viewed as a cornerstone of the franchise, his development has plateaued. Three straight below-average offensive seasons and a noticeable defensive regression in 2025 have raised real concerns about whether he can hold down shortstop long-term.
The Yankees won’t give up on him easily, but they also can’t ignore the trend. A fallback plan at shortstop — whether internal or external — may quietly climb the offseason priority list.
Urgency defines everything
The message from Cashman and ownership is clear: this is not a rebuilding year, nor will it ever be one as long as Judge is on the roster. The Yankees believe they’re still close — close enough that a few key additions could make all the difference come October.
Whether it’s another big bat, a proven starter, or bullpen reinforcements, New York knows this offseason can’t be about waiting and seeing. The time to act is now — before Judge’s window, and their own, starts to close.