When the New York Yankees freely let Didi Gregoius explore the open market after the 2019 season, it was jarring to fans who'd grown used to the foundation of the "era". Screw potential regression; undeniably, the 2017-2019 Yankees' "thing" partially ended when Gregorius entered the offseason to stone-cold silence. Thankfully, the Yankees managed to find an elite shortstop to replace him immediately! Kidding. They're still looking.
And while they were — sigh — right about Gregorius' future, his departure definitely created a vibes void, as well as an on-field hole. Things might've ended at the right time — Gregorius had an .827 OPS in the 2020 shortened season, then two brutal seasons in Philadelphia before he was shown the door by the league — but that doesn't mean losing the best version of him was an easy puzzle for the Yankees to solve.
Adding to the fracture was the oddness of his 2019 campaign. His grand slam/bat hold-and-drop in the ALDS healed all wounds, but he missed a large chunk of the year rehabbing from Tommy John and had some trouble fitting back into the "next man up" clubhouse. Was the friction genuine, or just perceived?
He reportedly returned from a 2019 rehab assignment taken aback by the Yankees' development processes (and might be vindicated on this particular take), voicing his concerns to the front office. In his Phillies intro press conference later that winter, Gregorius' words indicated coldness: he noted Brian Cashman "made it loud and clear that [Gerrit] Cole was their priority.”
Six seasons is quite enough time to do some serious reflecting on the callousness of the business, and if Gregorius left New York feeling disrespected (or if the Yankees felt jarred by his suggestions), it certainly seems like bygones are now bygones. Gregorius was spotted taking BP with the Yankees on the backfields on Tuesday ahead of his return to the diamond with Team Netherlands in the World Baseball Classic.
Didi Gregorius is taking batting practice at Yankees camp
— Talkin' Yanks (@TalkinYanks) February 10, 2026
Didi will play for Netherlands in the upcoming World Baseball Classic pic.twitter.com/YTi4Y8pF9f
Former Yankees fan favorite Didi Gregorius is on better terms with the organization
Yankees spring training is a long way from Dubai. Gregorius showing off his happy-go-lucky personality on the land he once ruled is a long way from what we perceived to be some lingering weirdness between the two parties, too.
Who knows? Maybe Gregorius' beaming, late-career smile is exactly the kind of vibes injection that the 2020-to-present Yankees have desperately needed. His good juju might be directly transferred to Jose Caballero at the perfect time.
