PITTSBURGH -- Derek Shelton’s first managerial opportunity came with the Pirates. On Friday, Shelton returned to PNC Park but in the opposing dugout as the Twins' skipper.
Shelton was dismissed by Pittsburgh on May 8, 2025, after four-plus years as its manager. The Pirates were 12-26, and current Pirates manager Don Kelly took over. Shelton finished with a 306-440 record as Pittsburgh’s manager.
“I wish it would have went differently, obviously,” Shelton said during batting practice Friday. “I think there were a lot of factors that come into play there. Some of them are out of my control. To look back on it -- I will never look back on it in a negative connotation, regardless of how anything went down.”
Shelton's dismissal was one of nine managerial changes during or after the 2025 season. He quickly transitioned into a media role, working with MLB Network and MLB Network Radio just a few weeks after his departure.
Shelton said he had fun in his foray into media, but he knew he wanted to return to coaching.
“This one lined up in a really good situation. It was something I debated at the end of the year," Shelton said. "'Do I want to continue to just do more media stuff and let that grow?' But I feel like I'm too young to do what [the media] does right now."
Shelton’s first year in Pittsburgh began under unprecedented circumstances with the shortened COVID season. He said he felt the pandemic had an effect on everyone in the organization in terms of building relationships.
Shelton has maintained a good friendship with general manager Ben Cherington. He credited the organization for their success in building pitching depth via the Draft.
“He's a guy that I admire a lot,” Shelton said. “I'm very happy that he was allowed to do some of the things he was allowed to do this year.”
Kelly served as a coach on Shelton’s staff for his entire Pirates tenure. Kelly said on Thursday that he learned a lot from Shelton, most notably regarding communication and how to tackle issues head-on. The two don’t talk regularly, but they still text back and forth at times.
Shelton’s new gig isn’t totally brand new to him. He served as the Twins' bench coach for the 2018-19 seasons. That prior experience brought him comfort when he accepted the managerial position, already knowing parts of the organization like their travel secretary and front office. Minnesota entered Friday’s game at 27-30.
Of course, Shelton had hoped he could help build a winner in Pittsburgh. But he's more than happy in his new chapter thus far.
"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."