Pirates insider's idea to save 2025 season comes with serious risk

Ben Cherington may have to tap into unprecedented aggression in order to save his job going into 2026.
Jun 5, 2024; Pittsburgh, Pennsylvania, USA;  Pittsburgh Pirates general manager Ben Cherington speaks on the phone in the dugout before the Pirates host the Los Angeles Dodgers at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
Jun 5, 2024; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington speaks on the phone in the dugout before the Pirates host the Los Angeles Dodgers at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

From on-the-field failures to off-the-field PR nightmares, nearly everything that could go wrong for the 2025 Pittsburgh Pirates has done just that. The club that has Paul Skenes and supposedly came into the season solely focused on winning barely has a better record than the 2020 team that started an exhaustive rebuild now in its sixth season.

General manager Ben Cherington spoke after the team dismissed manager Derek Shelton after a 12-26 start and made a stunning and tone-deaf remark. "I don’t think we have to squint too hard to see a better team on the field in 2025," the ever-inspiring and motivational Cherington said. He has preached of the importance of internal improvement, but despite coaching changes made both before and during the season, that has not come to fruition.

The clock on Skenes' time in Pittsburgh is already ticking, and that pendulum swings louder and louder as the team's offensive ineptitude continues to drag on. The 2025 Pirates now possess the MLB record for most consecutive games scoring four runs or fewer and are the only team in MLB averaging under three runs per game. Both of those factors led to TribLIVE's Kevin Gorman making a brash proposal.

"The Pirates need to add some pop to their lineup, which could require Cherington to do something out of the ordinary and make a bold move," Gorman said last week. That seems to be the easiest way for the Pirates to add a serious hitter, but such a move would certainly be out of character, especially for Cherington.

Pirates' Ben Cherington must add thunderous bat in trade to save his job - but how?

There is some recent precedent for consequential bats changing hands in the month of May—Luis Arraez was traded from Miami to San Diego just last year, and the Brewers acquired Willy Adames from the Rays in May 2021. Those teams were much further ahead of the curve than the Pirates currently are, though. The Padres were 18-18 when they pulled the trigger on adding Arraez and the Brewers were 21-23 upon trading for Adames. Each of those teams gained the offensive spark they were after and wound up in the postseason after winning upwards of 90 games.

Obviously, there isn't a player the Pirates could conceivably add at this juncture who would make that kind of impact. But they've got to add a bat that moves the needle more than Spencer Horwitz, Tommy Pham, or Adam Frazier.

Even with Jared Jones, Johan Oviedo, and Hunter Barco currently on the shelf, the Bucs still have ample pitching that could be dealt for a bat or two, whether that be a veteran (Andrew Heaney, Bailey Falter, Dennis Santana, David Bednar) or a young but promising project (Thomas Harrington, Mike Burrows, Braxton Ashcraft).

It may be too early to speculate what hitters might be available on the trade market, but the Orioles—perhaps the only team more disappointing than the Pirates in 2025—make sense as a trade partner. Baltimore (tons of young hitting, but bargain shopped for starting pitching instead of retaining Corbin Burnes) looks like the polar opposite of Pittsburgh. Other teams like the Blue Jays, Rays, Angels, and Nationals could also have interesting pieces to sell if their struggles continue.

There would certainly be mixed feelings about Cherington being the man in charge of striking such a deal. The most significant hitting prospects he's acquired via trade (Endy Rodriguez, Liover Peguero, Jack Suwinski) have not panned out, and nearly every veteran hitter he's brought in (aside from Joey Bart) has immediately gotten substantially worse upon joining the Pirates. There's very little reason to trust his ability to identify offensive talent at all.

It's important to point that out because Cherington's predecessor, Neal Huntington, made a desperate in-season trade that ended up being his downfall. After an 11-game winning streak put the team just four games over .500 in the summer of 2018, Huntington mortgaged the Pirates' future and turned three top prospects into Chris Archer, who started just 33 games for the Bucs and sported a 4.92 ERA.

While the Pirates need to add offense in the worst way, they simply cannot afford to make a big move that doesn't work.

Cherington has dug himself into an impossible hole by failing to check essentially every box that a small-market GM has to check—prospect acquisition and player development have been subpar (if not straight-up awful), and what little cash he has to spend on the major league product has been allocated very poorly. Making up for all that with one move simply cannot be done, but the Pirates have to be better offensively, and that can't happen solely with the guys they have in-house.

The Pirates may be best suited to make a bold addition to the lineup, but they absolutely must get it right. Failure to do so would almost certainly lead to Cherington enduring the same fate that Derek Shelton did.