Yankees fans — here we are again. Another October, another letdown, and now, as the smoke clears from a four-game ALDS exit at the hands of the Toronto Blue Jays, the front office is once again staring down a familiar offseason question: Who’s staying, and who’s going?
A whole crew of players are heading for free agency — Paul Goldschmidt, Luke Weaver, Ryan Yarbrough, Paul Blackburn, Amed Rosario, and yes, Trent Grisham and Devin Williams. Plus, Cody Bellinger is expected to test the market, and Jonathan Loaisiga’s option is up in the air. Translation: Brian Cashman’s phone bill is about to skyrocket.
Devin Williams: A Discount Bet on Dominance
You mention “Devin Williams” and some Yankee fans might flinch — 4.79 ERA in the regular season was nothing short of disappointing. But let’s not forget, this is the same guy who made hitters look ridiculous with that Bugs Bunny changeup in Milwaukee.
90 punchouts in 62 innings. That’s elite stuff — like, filthy stuff. The kind that doesn’t grow on trees. And because of that bloated ERA, Williams’ market value might be at its lowest point since his Rookie of the Year days. This is a classic low-risk, high-reward scenario. One-year “prove-it” deal? You’re basically buying stock in a rebound season. And with the Yankees’ bullpen bouncing between brilliance and blowups, a resurgent Williams could be the stabilizing force they desperately need.
Trent Grisham’s Breakout Year Came at the Wrong Price
Talk about the guy who had us all raising our eyebrows this season — Trent Grisham. On the surface? Career year. That .235/.348/.464 slash line and 34 bombs was pretty impressive, especially for a guy who once couldn’t crack .200.
But look closer, and the warning lights start flashing. Too many strikeouts. 137 in 494 at-bats — and it got worse when the lights were brightest. Ten Ks in 29 postseason ABs, no homers, and a .138 average from the leadoff spot.
And defensively the guy’s a two-time Gold Glover, but you wouldn’t know it from his -1 Outs Above Average in 2025. That’s not a dip — that’s a nosedive. Combine that with his history of low batting averages and the reality that this year’s numbers may be an outlier, and suddenly that potential price tag doesn’t look so appealing.
Cashman’s Calculus: Risk vs. Reward for the Yankees
Let someone else pay top dollar for what might be a new trend. The Yankees need certainty, not another “maybe” in the outfield. There’s a reason New York has fallen short in October year after year — too many gambles on players who can’t produce when it matters most.
So here’s the takeaway: bring back the guy with the nasty stuff who’s ready to bounce back, and let go of the guy who showed up for the regular season but ghosted in October. The Yankees don’t just need talent — they need timing. And that, my friends, is everything in the Bronx.
