Noah Hiles: Like him or not, Derek Shelton deserved better from the Pirates

Noah Hiles, Pittsburgh Post-Gazette on May 31, 2026

Published in Baseball

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PITTSBURGH — Derek Shelton had his usual smile when he first sat down to chat with local media Friday afternoon at PNC Park. It was his first time back to Pittsburgh since the Pirates fired him as their manager last May. He knew what questions were coming. And he did a fine job at answering them, one after another.

Shelton said nice things about the city, highlighting that he took his coaching staff to the Roberto Clemente Museum not long after checking into their team hotel. He was complimentary of Don Kelly, the man who was not only his bench coach for five-plus seasons but replaced him at the helm in Year 6. He expressed his happiness for the players and fans that this year’s team is competitive, a rarity for most of his tenure on the North Shore.

But the person he seemed happiest for was the man who — aside from this year — assembled every roster he had managed in the major leagues: Ben Cherington.

“Ben does a good job,” Shelton said of his former general manager. “Again, going back to it, the team that he's created now, I'm extremely happy for him. I still have a strong friendship with him. He's a guy that I admire a lot. I'm very happy that he was allowed to do some of the things he was allowed to do this year."

The last part of that final sentence certainly stands out. “This year” has been much different than any of the ones throughout the Shelton era.

The Pirates had a nine-figure payroll on opening day. They signed a free agent to a multiyear deal. They acquired two All-Stars and a top-100 prospect in three separate transactions. They extended their top-rated prospect less than a week after his major league debut.

The Pirates had an opportunity to do all of these things from 2020-25 — but didn’t. It would make complete sense if Shelton were bitter, regardless of how hard he attempted to hide it Friday.

"I can't live in a speculative world,” Shelton said. “You can go back and say if this would happened and if this would have happened, but everything happens for a reason. I'm where I should be.

I’ve previously reported on how Shelton felt about last year’s roster. He, along with many others throughout the organization, desperately waited for reinforcements to arrive throughout the offseason prior to the 2025 campaign. And when no moves of substance were made, he was left feeling helpless heading into his sixth year on the job.

Shelton was a sitting duck, and everyone knew it. It wore on him throughout spring training. Those around the team could feel the tension in the air. That tension impacted Shelton’s ability to manage his ball club, something he more or less admitted Friday.

“I think specifically the ability to listen,” Shelton said, “the attention to detail — I think there are some things, probably later, the last six months, that I wish I would have done differently.”

I won’t pretend to know Shelton incredibly well. I covered him for a few years. We had what I like to think was a pretty strong professional relationship — save for one instance at Wrigley Field in 2024. But from what I do know about him, I think he truly is happy with this new opportunity. He always spoke highly of the Minnesota Twins organization, and they clearly thought highly enough of him to make him their manager.

The Twins were expected to be among the worst teams in MLB this year. They entered this weekend three games under .500 and one game out of an underwhelming American League wild-card race. So far, his club is playing well above expectations, which is commendable.

Plenty of fans voiced frustration with Shelton’s management throughout his time in Pittsburgh. I, however, could never really decide how good of a manager he truly was. We never had the opportunity to see him manage a roster truly capable of competing for the postseason — one like his replacement was given heading into 2026.

I’m not suggesting these Pirates would’ve been any better under Shelton. The vibes within the clubhouse have been much better under Kelly, who has been fine overall since taking over.

But Kelly is managing the Pirates in a year when they truly seem committed to winning. It’s hard to argue Shelton ever received that opportunity. And like him or not, that’s something he deserved.

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