The Yankees’ owner’s patience is reaching its limits. Following the franchise’s latest premature postseason exit, the owner has allegedly given a strong message to Brian Cashman and his staff. For Hal Steinbrenner, a championship drought that has outstretched too long has become totally unacceptable.

In recent media interactions, Cashman acknowledged that Hal Steinbrenner was “frustrated” and “disappointed,” stressing the owner’s desire to secure another championship for New York remains as strong as ever. “He wants a championship here for him and his family,” Cashman shared with SNY. “They believed, many times, that we had a chance to do something…he knows, opportunity lost for all of us.” The front office’s rare acknowledgment shows the amount of pressure they are facing now.

That pressure has only magnified after confirmation that Carlos Rodón, Gerrit Cole, and Anthony Volpe all are expected to miss the start of the 2026 season.

Manager Aaron Boone declared that Cole would not be ready for Opening Day, while Rodon’s recent elbow surgery has sidelined him for a minimum of eight weeks. As if that was not enough, Vople’s offseason shoulder surgery will postpone his comeback until late April or May, leaving huge gaps in both the infield and rotation.

Cashman also acknowledged that Anthony Volpe’s shoulder injury is going to hurt his next season’s availability and performance more than the Yankees initially thought. Aaron Boone also shared updates about his SS in his end-of-season interview.

“The schedule would be for him to start hitting in four months… but he can’t dive on it or anything until six months. My expectation is that he’ll be delayed to start the season or starting a rehab assignment when we’re starting the season.” So, could they now pursue Bo Bichette and Ha-Seong Kim as insurance? All such questions are to be answered by the team, who are suddenly riddled with health issues, and an owner looking for answers.

In this situation, Aaron Judge remains the ray of hope.

The star will not need any elbow surgery and is expected to join the team as the full-time right fielder when 2026 begins.

Still, Steinbrenner’s frustration and multiple stars’ injuries have highlighted one thing that the Yankees management needs to deliver tangible outcomes, or a sweeping offseason transformation could become inevitable.

With vital stars sidelined, the management is now exploring trade options before Opening Day.

Yankees projected to target NL All-Star amid Bellinger uncertainty

After the current update that Cody Bellinger could enter free agency specifically, after the star denied a $25 million deal by the Yankees, they are targeting a vital trade to fill the gap in the outfield. Jim Riley thinks that the team could make an approach to reigning Cardinals All-Star Brendan Donovan.

He is a versatile hitter and is identified for a contact-driven approach and his defensive flexibility. The star’s skill to handle infield and outfield positions makes Donovan a suitable fit for the Yankees.

In 2025, Donovan, who scored .287/.353/.422 demonstrated exceptional plate discipline and situational hitting that the Yankees’ lineup urgently requires.

Riley described that his presence might allow New York to reshuffle Jazz Chisholm Jr. between positions, enhancing the lineup’s defensive coverage and depth. With Trent Grisham and Bellinger both testing the market, Donovan’s all-around versatility could be exactly what Cashman needs to reinstall consistency and balance for a clubhouse facing one of its most debatable offseasons in years.

The Yankees are now standing at a crucial juncture, one defined by injuries, roster uncertainty, and the owner desperately demanding immediate outcomes. Whether it is through a high-impact trade or by a bold free-agent move, Brian Cashman needs to act decisively to reclaim trust.