Ben Cherington's unfathomable trade deadline should conclude his tenure as Pirates GM

The Pittsburgh Pirates were above .500 and in the playoff hunt approaching the 2024 trade deadline. The team's measly attempt to masquerade as deadline buyers (bulking up the lineup with Isiah Kiner-Falefa and Bryan De La Cruz and shoring up the bullpen with Jalen Beeks) marked the beginning of a second-half collapse that saw the Pirates match their 2023 win total. General manager Ben Cherington caught plenty of heat for how he handled that trade deadline.

This year's performance was much, much worse.

The Pirates have been obvious sellers for essentially the entire season. Once manager Derek Shelton was fired after a 12-26 start, there was clearly no turning the ship around, at least not quickly enough for the rest of the 2025 campaign to matter. After operating as a prominent July seller for most of his tenure, Cherington has known for months that he needed to prepare for this exact situation.

In the days leading up to this year's deadline, Cherington spoke on multiple occasions about "needing to deliver more to (the) fans" and how his "only focus" was to improve the 2026 club, specifically the team's putrid offense. There were two ways to go about this.

The first option would be to keep players under control beyond this season and deal only rentals for whatever lottery-ticket prospects and salary relief that may provide. The team dealt Adam Frazier earlier in July and, by trading Kiner-Falefa, Tommy Pham, Caleb Ferguson, and Andrew Heaney, could free up around $6 million while opening the door for younger players to establish themselves as key members of the 2026 club.

The second option involves trading all of those guys, plus some players who are under control beyond 2025 who would be able to net offensive talent in return while also creating future financial flexibility. That would likely include starting pitcher Mitch Keller (owed roughly $60 million through 2028), third baseman Ke'Bryan Hayes (due an AAV of $7.5 million through 2029), and relievers David Bednar and Dennis Santana, each of whom have one more season of salary arbitration.

Cherington managed to pull off the worst of both worlds. In all, he traded Frazier, Ferguson, Hayes, Bednar, Bailey Falter, and Taylor Rogers (acquired in the Hayes deal on Wednesday). He did not trade any of Kiner-Falefa, Pham, or Heaney, all of whom are on expiring contracts and were all but guaranteed to be moved. That's three aging veterans who will be clogging up playing time down the stretch and who now have to adjust their mindset from preparing for a playoff hunt to being stuck in Pittsburgh.

By holding on to Keller, the Pirates passed on the opportunity to get legitimate offensive talent in return for a proven, controllable starting pitcher (very few of those were moved this deadline). A Keller deal also would have freed up the most money ($16.5 million just next year) to reallocate towards a bat or two in 2026. The quickest way to accelerate the offensive rebuild would have been to trade Keller, and they didn't.

The decision to keep Keller meant that Cherington absolutely had to maximize the returns for the controllable players he did move, and those results were extremely underwhelming.

Trading a former franchise cornerstone (Hayes) to a division rival certainly hurt, but that swap at least netted the Pirates a top-10 prospect (albeit one far from reaching the big leagues) and another high-priced veteran the team eventually managed to flip at minimal financial cost. Even considering Hayes' Platinum Glove-caliber defense, moving on was probably the best-case scenario for all parties involved.

Given the crazy prices some teams paid for controllable relievers, the Bednar trade was the Pirates' best opportunity to add an impact bat. They settled for catching prospect Rafael Flores, who tore up Double-A pitching this year, but at age 24. He looked overmatched upon his promotion to Triple-A and will report to Indianapolis. The other two prospects the Pirates received are still in A-ball. Hard to see how that trade helps the Pirates get better in 2026.

Even more baffling was the Falter trade. PNC Park was tailor-made for Falter (3.79 career ERA in Pittsburgh, 4.76 ERA everywhere else), and the team was under zero obligation to move him now. His 2025 salary (in his first season of arbitration eligibility) is just $2.22 million, and he isn't slated to hit free agency until after the 2028 season. The only reason to move him now was for the perfect package. And to Cherington, that package was a 28-year-old relief pitcher with 5 1/3 career MLB innings (who is being sent to Triple-A) and an A-ball first baseman who went undrafted last year. Seriously.

Knowing the Pirates' track record for developing hitters, it can be argued that the team acquired a whopping zero hitters who will help the team in 2026. They didn't clear enough future payroll to add an impact bat (especially if it's as hard to trade for established hitters as it was at this deadline). And with multiple rentals still in the fold, young players who could have been put in position to prove themselves ahead of next season (Nick Yorke, Billy Cook, Cam Devanney, Bubba Chandler, Hunter Barco, Thomas Harrington) will have fewer opportunities.

What seems lost on the front office is that Paul Skenes is still a Pirate. One of the most talented pitchers in the history of the sport fell into their laps and there's still zero urgency to compete with him in the fold. Next year is his last as a pre-arbitration player, meaning his salary starts to go up considerably in 2027. They have to cash in now.

Ben Cherington has survived multiple epic failures with Pirates that other franchises simply would not have allowed

The Pirates' patience with Cherington continues to be baffling. The case could be made that he should have been fired after last year's unsuccessful trade deadline, or over the winter when he failed to funnel adequate resources into the MLB roster, or earlier this season when Shelton was fired, or after this year's draft when he inexplicably ignored the possibility of the club's second-round pick honoring his college commitment and not signing.

This has to be the final straw. Cherington cannot be allowed to make any more important decisions for this team and continue to set the franchise back. Nearly every effort he's made in six years to add hitters have failed, and after this trade deadline it looks like he stopped trying. The Pirates need to win soon, but it can't happen this way.

Ben Cherington has to go.