Pirates showed historic patience with failing management before Derek Shelton firing

The Pittsburgh Pirates have hit rock bottom.

The 2025 season has already produced a plethora of PR disasters for Bob Nutting and Travis Williams' club—a crowd of nearly 37,000 broke out into multiple "Sell the team!" chants during the team's home opener (a game which the Bucs lost, 9-4); Roberto Clemente's retired No. 21 was replaced (literally on the Clemente Wall, no less) by an advertisement; the "Bucco Bricks," formerly housed outside of PNC Park, were removed during renovations and found dumped in a landfill; a fan fell 21 feet onto the field mid-game, suffering critical injuries; earlier this week, a fan and a PNC Park employee got into a nasty altercation that required security and police intervention. All of that has happened just 38 games into the 2025 campaign.

The Pirates won just 12 of those games. In addition to becoming a non-stop PR catastrophe, the on-field product has been terrible. Despite possessing a generationally talented ace, watching a breakout season from their immensely gifted slugger, and seemingly striking gold on a bargain free agent signing, the Pirates have won less than a third of their games and have MLB's third-worst record.

After the 2024 season, which saw the Pirates finish with a 76-86 record for the second consecutive season, general manager Ben Cherington said that he and manager Derek Shelton, who both were hired before the 2020 season, would go into 2025 "accountable together" and "excited for the work ahead."

The immediate work ahead included overhauling the major league coaching staff, trading for an inexperienced first baseman with chronic wrist issues (who still has yet to officially don a Pirates uniform), spending a sizeable chunk of the offseason budget on Tommy Pham and Adam Frazier, and neglecting to replace the departing Aroldis Chapman as insurance for their once-dominant closer coming off of a near-6.00 ERA.

Now here the Pirates sit, a week and a half into the second month of the season and further below .500 than the team has fallen at any point since the end of the 2022 campaign. And now Cherington has removed "together" from the accountability equation and relieved Shelton of his managerial duties. While Shelton is the lone fall guy, at least for now, Cherington should certainly shoulder substantial blame for the current state of the organization.

Ben Cherington's tenure as Pirates GM has been historically bad

Upon his hiring, Cherington's entire agenda was to engage in a full-scale rebuild, stripping the roster of whatever veteran players remained and committing to stockpiling as much young talent as possible. He largely succeeded, trading the likes of Starling Marte, Josh Bell, Joe Musgrove, Jameson Taillon, Adam Frazier, Clay Holmes, Richard Rodriguez, Jacob Stallings, Jose Quintana, and Carlos Santana for prospects while consistently picking high in the draft, never selecting later than ninth and securing the No. 1 pick twice.

While he netted Paul Skenes with one of those top picks, the other was used on Henry Davis, who has a .578 OPS through his first 410 MLB plate appearances. While Skenes and Jared Jones (and hopefully Bubba Chandler) have been developmental successes on the mound, nearly every young bat developed by this organization has flopped upon reaching the big leagues.

Executing a rebuild was not expected to be a quick process, especially in a small market like Pittsburgh. So the fact that Cherington has stuck around this long isn't exactly earth-shattering. But that he has done so without winning anything—and still remains in the picture—puts him in pretty rare company.

Cherington began his Pirates tenure with five consecutive losing seasons and was brought back for a sixth season. According to The Baseball Cube's MLB General Manager database (which, for some franchises, dates back to the 1930s), he's just the 14th GM in league history to be afforded that privilege with any team. But even among that group of underwhelming executives, he still stands out.

The Pirates' 294-414 record in Cherington's first five seasons prorates to a 95-loss pace across a 162-game season. Among the other 13 general managers on that list, only three of them won with less frequency than Cherington in their first five seasons—all three were running expansion teams.

Some of those men who were granted long leashes did end up seeing the fruits of their labor. Pat Gillick was one of those expansion GMs who wound up winning consecutive World Series in Toronto. Terry Ryan lost for six years in Minnesota before averaging 89 wins over the next eight seasons. Dayton Moore managed to take the small-market Royals to two World Series, winning one. The only other qualifying active GM, San Diego's AJ Preller, has far more money to spend and is a notoriously aggressive negotiator on the trade front.

It's clear that Cherington and the Pirates won't find any success by maintaining the status quo. He must operate differently than he has and pursue new avenues to improve this team. Another note on those other general managers—all of them who eventually won did so with a different manager than they started with. That brings us to Shelton:

Derek Shelton's tenure as Pirates manager wasn't any more impressive

Using the same criteria as before, Shelton finds himself in an even smaller class. He was just the fourth manager to ever be granted a sixth season after five losing campaigns. Shelton's .415 winning percentage was the worst of that group, which also included the manager of an expansion team.

Earlier in his coaching career, Shelton was a hitting coach, which surely contributed to the perplexity surrounding the Pirates' inability to develop hitters. Henry Davis, Ke'Bryan Hayes, Jack Suwinski, and Endy Rodriguez (among many others) all were either top prospects or showed early promise at the MLB level before fizzling out. Between the offensive ineptitude, the Pirates' lack of "winning in the margins," and Shelton's frequent bullpen mismanagement, his downfall felt inevitable.

The Pirates' recent losing skid secured Shelton 214th place in wins among the 216 managers with at least 700 games under their belt.

The difference is that Wilson and Gomez (and even Chapman, for that matter) had to accrue 700 games of experience in smaller stints with multiple teams. The Pirates endured 746 games with Shelton before deciding that enough was enough. He, too, could eventually get another opportunity if he can prove that he didn't lose the clubhouse by early May.

How can the Pirates turn things around after Derek Shelton's firing?

FanSided's Robert Murray makes a great point—the root of the Pirates' problems wasn't Cherington or Shelton, but owner Bob Nutting, who has served in that capacity since Jan. 2007. It's well established that Nutting does not grant the Pirates the ability to spend like other teams—the team has consistently had a bottom-10 (and typically, bottom-five) payroll under his leadership, and the club's $26 million deal with Ivan Nova in Dec. 2016 remains their most recent multi-year free agent commitment.

Nutting's claim last month that he has provided enough resources to the team was a slap in the face and an insult to the intelligence of the fans who continue to invest time and money into watching the Pirates. Any general manager who had to resort to signing Tommy Pham, Adam Frazier, and Tim Mayza to fill gaping holes in the roster clearly does not have adequate resources at his disposal.

But Ben Cherington's job is to assemble the best baseball team that he can, and he clearly has not done that.

Derek Shelton's job was to get the most out of the roster he was given, and he clearly did not do that.

Shelton's dismissal was a start, but the Pirates have been far, far too patient. More changes, either in philosophy and execution or personnel, must be on the horizon.