2 near unforgivable Brian Cashman mistakes on full display for Yankees early in 2026

The New York Yankees' "run it back" philosophy was validated eight games into the 2026 regular season. The team was 7-1. It appeared general manager Brian Cashman had executed a genius, underappreciated offseason! The overreactions spilled forth.

Very quickly, all of that went away. Before a miraculous win on Monday night (which should have been a loss), the Yankees had lost five straight and six of seven, self-sabotaging what would have been a valuable early cushion atop the entire American League.

Even more frustrating for Yankees fans was to see some of their common gripes with Cashman's roster construction rising once again to the surface as enduring issues. Most notably, the Yankees' bullpen situation remains a mess, and Cashman's refusal to go out and acquire a serviceable shortstop still reflects poorly.

The Yankees' 2026 bullpen is an absolute disaster

New York's 'pen is, on the whole, a collection of unpredictable arms that have shown flashes of brilliance but ultimately can't be relied upon to any extent. Not great, Bob. Tim Hill remains a low-key stalwart, and Fernando Cruz and David Bednar — though flawed — have been okay enough to avoid serious criticism.

But everyone else? Yeah, they can go. Some are already on their way. Jake Bird was optioned to Triple-A Scranton/Wilkes-Barre on Monday night following another bad performance (three earned runs, four hits allowed in an inning of work). Camilo Doval has already completely undone his promising start to 2026, proving that he's still, in fact, not who Cashman thought he was.

Will the return of Gerrit Cole and Carlos Rodón push some arms of decent quality into the 'pen, guys like Ryan Weathers? Sure. And the Yankees might also be bolstering the unit with a Yovanny Cruz promotion soon (or better yet, Carlos Lagrange, if they're feeling competent).

But for every potential bullpen "solution" for the Yankees, there seems to be another front office bullpen gaffe staring fans in the face. Rest in peace, Yankees Cade Winquest and his zero appearances in pinstripes.

Brian Cashman's refusal to sign a real shortstop for Yankees is deranged

The Yankees had a very respectable phase with Didi Gregorios at shortstop from 2015-2019, but on the whole, the franchise has failed to adequately fill the position since Derek Jeter's retirement. Are we asking to go out and find someone to fill Jeter's shoes? Uh, no, that would be an outrageous and impossible request.

But I'm pretty sure the New York Yankees can do better than their current Anthony Volpe/Jose Caballero situation that leaves plenty to be desired.

While we're on the topic of Jeter, was Caballero's vulgar celebration against the Tampa Bay Rays the least Jeter-like (i.e. classy) action during a game from a Yankees player in franchise history?

The Yankees don't need a Hall of Fame shortstop to win a title in this Aaron Judge era. They have Hall of Famers at other spots. But for Cashman to be sated with the situation at short over the past few years, continually expecting Volpe to emerge as "the guy" — well, that's not exactly Hall of Fame GM behavior, especially when he passed on so much previous talent and didn't properly address the position knowing Volpe would be missing the first 6-8 weeks of the regular season.

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