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Trent Grisham’s $22 Million Deal Blew Up in the Yankees’ Face, and Now Everyone’s Watching

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New York Yankees logo on gradient background
New York Yankees logo on gradient background — Created by the Sports On Tap desk | Source : Sports On Tap (team logos property of their respective owners)

The New York Yankees’ season just slammed shut on Wednesday with a brutal 4-3 loss to the Tampa Bay Rays, capping a sweep that means a staggering 17 straight years without a World Series title. Now the front office has to make a seriously tough call on their outfield, and honestly, they can’t afford to mess it up again. Sports Illustrated is reporting that the team simply cannot re-sign Trent Grisham for the 2027 season, and look, letting him walk is the *only* logical step if they want to get this team right.

That $22 Million Bet Totally Flopped

Remember last November when Grisham signed that one-year, $22.025 million deal? He accepted the qualifying offer after crushing a career-high 34 home runs in 2025. Yeah, well, 2026 was a whole different story, and it’s not pretty. The dude, who’s about to hit 30, only managed to hit .211 with a paltry 18 homers this year. His defense and speed? They came under heavy fire, especially during the playoffs. He went a terrible 2-for-15 in five playoff games, including against the Rays, and get this: one of those “hits” was actually on a failed sacrifice bunt attempt. Seriously? That $22 million bought absolutely none of the results they desperately needed.

The good news is the Yankees have a clear path forward without him. They can definitely keep Aaron Judge and Cody Bellinger, and then bring in some real younger talent. Spencer Jones and Heliot Ramos are already on the roster, ready to go. And Jasson Dominguez? He could absolutely make a big return if he just cleans up his defensive issues. Holding onto Grisham would be a massive waste of funds, money that could actually upgrade a seriously weak spot on this roster. This team needs fresh legs, not a player who struggled to even hit the ball.

Change Is Coming, Like It Or Not

This endless failure to win has lit a fire under everyone, sparking loud calls for a massive shift in direction. Stephen A. Smith, bless his heart, laid it all out on Thursday, calling out the 17-year championship drought and reminding everyone they’ve only got one title since 2009. His words were sharp: “There needs to be change.” He didn’t outright demand manager Aaron Boone’s firing, but his message was crystal clear. Smith called the lack of a title “unacceptable” for a franchise with this kind of history.

The pressure is on the front office, big time. They can’t just cross their fingers and hope things magically get better. The Rays completely swept the series, winning Games 1 and 2 down at Tropicana Field. But Game 3 at Yankee Stadium? That was pure heartbreak. Anthony Volpe looked like he’d tied the game with a home run, only for a fan interference call to overturn it into a double. A DOUBLE! And here’s the kicker: the Yankees never held a lead in any of the 27 innings of that entire series. Ben Rice summed it up perfectly after the final out: “As far as I’m concerned, it’s a failure since we weren’t able to get the job done.” He didn’t mince words, adding, “They outpitched us, out-hit us. It’s really that simple.” The front office has to act. Letting Grisham walk is the only way this team starts to fix what’s broken for 2027.

This article was created with AI assistance and published under Seattle On Tap’s editorial standards. See our Editorial Policy.

Originally reported by Yahoo Sports.

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