The New York Yankees are having a drama-filled offseason with the front office complicating things for themselves. While the other teams’ strategy is to improve on their past mistakes, Brian Cashman seems to be doing the same thing he has done previously. And this time, it might cost them more than a few games becuase they might now lose out on Tarik Skubal, who the team was actually needs.

After the $22 million qualifying offer was accepted by Trent Grisham, many fans were not happy. Although Grisham had a great 2025 season offensively, his overall season was not very good. And now this has forced Cashman to consider the top trading piece as a backup for Grisham. In a recent interview, Cashman said, “We have the kids Jason Dominguez and Spencer Jones… we have Jason Dominguez and Spencer Jones competing, and we have Grisham… those two kids fight it out and may the best person win and see where that takes us.”

The Yankees were reportedly considering acquiring Tarik Skubal from the Detroit Tigers this offseason. The proposed trade included Spencer Jones, Will Warren, Carlos Lagrange, and Bryce Cunningham, all young talents with high upside. Skubal finished 2025 with a 2.21 ERA across 31 starts, earning two consecutive AL Cy Young Awards. The plan aimed to strengthen the rotation while giving the Tigers a strong pipeline of pitching prospects.

Trent Grisham’s acceptance of the $22.025 million qualifying offer now complicates the Yankees’ financial flexibility. Grisham hit a career-best 34 home runs with 87 RBI in 2025 but struggled in the postseason. Over 10 postseason games after the NLCS, he collected only three hits in 39 at-bats, striking out 17 times. These offensive struggles forced the Yankees to reconsider how to balance outfield roles and budget allocations for 2026.

Spencer Jones is emerging as a potential starter in left field following Grisham’s return, impacting trade options. Jones produced 35 home runs, 80 RBI, and 29 stolen bases across Double-A and Triple-A last season. With Jones likely to occupy a critical outfield spot, the Yankees lose leverage in the Skubal trade package. This development significantly reduces the probability of completing a deal for Skubal while managing the 2026 outfield composition.

Brian Cashman now faces a high-stakes puzzle, juggling Grisham, Jones, and budget constraints strategically. The Yankees’ hopes for Skubal appear distant, as top prospects are now anchored in the outfield. Fans can watch as Cashman’s predictable moves turn into an offseason soap opera of calculated chaos.

Another previous Yankees trade rumor is starting to gain traction

The Yankees’ offseason has a familiar whiff of chaos, and Brian Cashman seems perfectly comfortable steering the ship through it. While most teams are quietly weighing options, New York is quietly eyeing moves that could shake the AL East to its core. If you’ve been paying attention, you know Cashman doesn’t do subtle; he prefers headlines, rumors, and deals that make fans simultaneously cheer and groan.

Brendan Donovan, 29, had a breakout 2025 season, hitting .287 with 10 home runs. He drove in 50 runs over 118 games despite missing most of August and September. Donovan earned his first All-Star selection, showcasing both offensive production and defensive versatility. Following groin surgery in October, he is expected to be fully available for 2026 spring training.

The Yankees have multiple infield questions, particularly with Ryan McMahon’s inconsistent bat and Jazz Chisholm Jr.’s shifting role. Donovan’s ability to play multiple positions would allow New York to optimize its lineup. His age and arbitration control for two more seasons align with the team’s championship window. With the Cardinals reportedly willing to trade Donovan, the Yankees could address immediate roster gaps effectively.

If the Yankees move for Donovan, Brian Cashman would prove he still plays chess, not checkers. New York’s infield could transform overnight, forcing fans to reconsider who really belongs in the lineup. With the Cardinals willing to negotiate, the Yankees might finally turn offseason rumors into tangible results.