Twins are threatening fans with the sad lesson Pirates know all too well

The headline almost writes itself for beleaguered Twins fans: Minnesota is flirting with hiring former Pirates manager Derek Shelton. But here’s the twist: while the Twins fiddle with a new voice in the dugout, the front office is busy pulling the plug on near-term competitiveness. From the Pirates’ perch, watching Minnesota jettison talent and dial back ambition is like staring into a mirror, only this time it’s someone else’s reflection, and Pirates fans are the ones holding the popcorn.

Because let’s be clear: the Twins don’t have October ambitions. They don’t even have September hopes, really. Ownership and leadership are actively engaging in a roster teardown. They traded away Jhoan Duran, Carlos Correa and multiple key contributors, shed tens of millions in payroll, and indicated they’re prepping for a full-on reset.  Meanwhile, hiring someone like Shelton, whose entire tenure in Pittsburgh was a series of losing chunks, win-rates under .420, and zero winning seasons, isn’t so much ironic as it is a comedic sketch. Pirates fans nod knowingly: yes, we’ve seen this movie before.

Twins consider Derek Shelton while waving the white flag on 2026

Shelton’s time in Pittsburgh ended ignominiously, 38 games into the 2025 season after a 12–26 start. He closed out with a 306–440 managerial record (.410). He faced criticism for stalled player development (see: the Ke’Bryan Hayes failed experiment), questionable in-game decision-making, and yes, an ownership structure that refused to give him a roster capable of meaningful lift. All true.

Now let’s hand it to Minnesota. They’re signaling very loudly that this isn’t about “retooling to win now,” it’s about rebuilding from the ground up. The Twins, who until recently enjoyed something like “good times under-the-hockey-stick” performance, now seem comfortable saying: “Let’s sell the chips, clear the board, and play prospect bingo.” If Pittsburgh were writing a cautionary manual for rebuilding teams, Minnesota would have bookmarked the chapter.

So why bring Shelton into this scramble? He may well be viewed as a low-risk option, someone who knows what it’s like to manage under resource constraints, to scratch out wins quietly and lose big loudly. In the Pirates’ world, characterization: there’s the guy who leads you through the injury list, the thin bullpen nights, the $60 million payroll top-heavy with “hope.” That fits Shelton’s biography in Pittsburgh. Change the city, same script. But if Minnesota actually hopes to emerge competitive sooner rather than later, convenience hiring someone with 0 winning seasons might not be the bold move fans expect.

Pirates fans can’t help but grin a little. The Twins are about to learn what they’ve already lived: that losing isn’t a glitch, it’s a process, an institution. If Minnesota hires Derek Shelton while simultaneously purging talent and shrinking payroll, they’ll discover what happens when the margin for error disappears. Good luck to the fans over there, those in Pittsburgh have already taken notes.