Pirates spending surge comes with cruel Derek Shelton twist

The Pittsburgh Pirates' payroll — which ended last season around $87 million — has ballooned to more than nine figures ahead of 2026, which is the largest total spent by the franchise in a decade. It (hopefully) marks the beginning of a new competitive era of Buccos baseball, with new additions Brandon Lowe, Marcell Ozuna, Ryan O'Hearn, José Urquidy, and Gregory Soto (among others) joining forces with a tantalizing young core.

Just about everyone in the Steel City is smiling, even if Bob Nutting could still stand to spend a few more dollars on the roster. But do you know who isn't having the time of his life right now? New Minnesota Twins manager Derek Shelton.

The former Pirates skipper — who oversaw a rough tank job between 2020 and the first quarter of the 2025 season — returned to the Twin Cities this offseason with the intention of moving past his ugly managerial tenure in Pittsburgh.

Instead, his new team has slashed payroll by more than $30 million this offseason, all but plunging head-first into a tanking period they began at the 2025 trade deadline. Talk about a bad beat.

Derek Shelton, Pirates heading in different directions ahead of 2026 season

The Shelton era in Pittsburgh wasn't pretty; the team went 306-440 under his stewardship, including three last-place finishes in the NL Central. They never finished any season in that time better 10 games under .500.

Now, part of that was by design — and Nutting's refusal to spend certainly didn't help matters — but it became immediately clear that the team made the right call in moving on when interim manager Don Kelly piloted the team to a 59-65 record to close out 2025, a winning percentage of .476 that was better than any individual season under Shelton.

With Kelly now leading the charge and so much new talent in the fold, Buctober finally looks like a realistic dream again.

Meanwhile, Shelton and the Twins figure to be in for a rude awakening in 2026. The roster is still reeling from the losses of Carlos Correa, Louis Varland, Willi Castro, and others at last year's trade deadline, and the front office has spent the entire offseason dumpster diving for veteran players who could be turned into prospects come this July.

One thing at least working in Shelton's favor is that he was the Twins' bench coach from 2018-19, but that familiarity will only matter so much to a roster that's undergone so much turnover and turmoil. Less than a year after escaping the Pirates' rebuild, it appears that the veteran manager is in for another period of excess losing.