Former Pirates Manager Wishes He Got More Roster Investment
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PITTSBURGH — The Pittsburgh Pirates usually don't make many moves in the offseason, but they changed that this winter, prompting surprise from their former leader.
Derek Shelton, who was the Pirates manager for most of this decade, is now the manager of the Minnesota Twins, who the Pirates hosted at LECOM Park in Bradenton, Fla. on Feb. 26 for a Grapefruit League matchup in Spring Training.
Shelton was intrigued with the offseason the Pirates, wondering why the Pirates never did that under his tenure, but also was happy for the team and that general manager Ben Cherington made those moves, which will make them a better outfit in 2026.
He is also excited to see how those moves line up with already having Cy Young award winner Paul Skenes and the best prospect in baseball in Konnor Griffin.
"I think at some point you wish you would have seen the investment that they saw this offseason, but good for them," Shelton said in a video from DK Pittsburgh Sports.
"I’m very happy for Ben [Cherington] that he had the ability to go out and acquire guys. They’re a better club than they were probably at any point in the tenure here with the people they’ve added, and it’s going to be exciting to see.
"They have the best pitcher in the game, obviously. They have the best prospect in the game, who is uber-exciting to watch. I’m a little disappointed he’s not in the lineup today because he’s a guy that you want to watch. I’m happy for Pirates fans that they got the investment they did this offseason.”
Lack of Moves for Pirates Under Derek Shelton
The Pirates didn't make many serious moves under Shelton, which definitely played a role in him not having the success he wanted while in charge.
Pittsburgh also underwent a massive rebuilding stage during Shelton's tenure, following the end of former manager Clint Hurdle and former general manager Neal Huntington's tenure.
The Pirates never made a multi-year free agent signing, finally doing so this past offseason in Ryan O'Hearn for two years, $29 million.
It was the first multi-year free agent signing for the Pirates since right-handed starting pitcher Iván Nova for three years, $27 million on Dec. 27, 2016 and the first position player free agent signing for more than one year since John Jaso for two years, $8 million on Dec. 23, 2015, a decade prior.
Biggest Free Agent Signings Under Derek Shelton
Player | Position | Contract | Year Signed |
|---|---|---|---|
Aroldis Chapman | Relief Pitcher (L) | $10 million | 2024 |
Rich Hill | Starting Pitcher (L) | $8 million | 2023 |
Martin Perez | Starting Pitcher (L) | $8 million | 2024 |
Carlos Santana | 1B/DH | $6.725 million | 2023 |
Austin Hedges | C | $5 million | 2023 |
Andrew McCutchen | OF/DH | $5 million | 2023, 2024, 2025 |
Roberto Pérez | C | $5 million | 2022 |
Tommy Pham | OF | $4.025 million | 2025 |
Michael A. Taylor | CF | $4 million | 2024 |
Yoshitomo Tsutsugo | 1B | $4 million | 2022 |
Most of these deals filled an immediate role, but didn't make the Pirates better for the long term in the future.
The Pirates also failed to add effectively at the 2024 trade deadline, as they were 55-53 overall and in competition for a National League Wild Card spot.
Pittsburgh's big additions were Isiah Kiner-Falefa and Bryan De La Cruz, missing out on the likes of Jazz Chisholm Jr. and Yandy Díaz.
Kiner-Falefa played many positions, but provided little power, and De La Cruz slashed .200/.220/.294 in 44 games, with the Pirates non-tendering him after the season, making him a free agent.
Chisholm was an All-Star and Silver Slugger Award winner with the New York Yankees in 2025, who did trade for him, while Díaz earned MVP votes.
The Pirates would go 8-19 in August and finish 76-86 overall for the second straight season.
Pittsburgh adding Tommy Pham and also Adam Frazier to one-year contracts did little to inspire the fan base, who demanded owner Bob Nutting sell the team throughout the season.
Shelton struggled with the Pirates in 2025, going 12-26 before they fired him on May 8 and replaced him with bench coach and current manager Don Kelly.
Dominic writes for Pittsburgh Pirates On SI, Pittsburgh Panthers Pn SI and also, Pittsburgh Steelers On SI. A Pittsburgh native, Dominic grew up watching Pittsburgh Sports and wrote for The Pitt News as an undergraduate at the University of Pittsburgh, covering Pitt Athletics. He would write for Pittsburgh Sports Now after college and has years of experience covering sports across Pittsburgh.