Remember when the New York Yankees decided to give a qualifying offer to Trent Grisham, and he accepted it? That was probably the day the Bleacher Creatures knew that this offseason was not going to be a good one. But it looks like this feeling was not limited to fans alone.

In a recent show with Joel Sherman, Jon Heyman was asked which was the worst signing of the offseason for the Yankees. And Heyman had only one answer.

“I think it’s giving Grisham the qualifying offer,” said Jon Heyman. “I don’t mind that they brought the team back. Grisham at 22 million. That’s an overpay.”

The Yankees’ offer guaranteed $22.025M for 1 year, a figure tied to league qualifying rules. Grisham’s acceptance ended free agency talks quickly and locked roster decisions before other moves began. It also removed draft-pick compensation questions, since accepting players cannot be traded freely.

Trent Grisham accepted because his 2025 season raised doubts about matching $22M annually elsewhere. He hit .235 with 34 home runs, but his overall value remained widely debated leaguewide. Defensive metrics dipped in 2025, weakening arguments for a long, expensive contract elsewhere.

Industry projections placed his annual value below $22.025M across multiyear scenarios.

Before acceptance, many expected New York to let him test free agency briefly. Criticism centered on opportunity cost, with center field blocking younger outfield paths.

That mood shifted temporarily as rumors linked New York to Tucker, Diaz, and Imai. Those links softened reactions.

But as weeks passed, tangible moves lagged, and the lineup increasingly resembled last season again. Aside from additions like Ryan Weathers, core positions remained largely unchanged entering camp periods.

In hindsight, the qualifying offer itself created pressure as roster flexibility narrowed steadily afterward. Some fans recognized early that acceptance would complicate outfield plans and prospect timelines. Those concerns materialized once Grisham officially occupied center field for another guaranteed season ahead.

The situation mirrored prior logjams where veterans had limited opportunities despite organizational depth charts.

When Jon Heyman labeled the deal an overpay, the math supported that conclusion.

The Yankees paid the maximum qualifying figure instead of negotiating a lower open-market rate. Ultimately, the decision followed rules and numbers, leaving emotions to follow facts afterward publicly.

Is it bad that the Yankees are running it back for the 2026 season?

There is a thin line between stability and stagnation, and it has been tested before winter even settled in. Familiar decisions arrived early, flexibility vanished quickly, and the direction felt decided without saying it out loud. Once Trent Grisham stayed, the Yankees followed a path Brian Cashman knows well, for better or worse.

The front office signaled continuity after Brian Cashman called the roster strong at the Winter Meetings. They reinforced that stance by re-signing Bellinger for five years and $162.5 million.

Seven projected starters appeared in the final 2025 playoff game, eight without Anthony Volpe’s surgery. Aside from lefty Ryan Weathers, the rotation and bullpen largely mirror last season’s roster usage.

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That familiarity reflects 2025 results, which fell short despite a 94-68 record and division expectations. The Yankees tied Toronto for the AL East, then lost 3-1 in the ALDS series.

A midseason slump and post-deadline losses in Miami triggered Giancarlo Stanton’s clubhouse meeting. Yet the offense led MLB with 849 runs and a 119 wRC+, league-best.

That production returns mostly intact, anchored by Aaron Judge and steadied by Cody Bellinger. Ben Rice follows a strong rookie season, while Trent Grisham brings last year’s gains. The rotation bridges injuries, with Max Fried leading until Carlos Rodón and Gerrit Cole return.

Running it back reflects trust in numbers, with betting odds ranking the Yankees second overall.