MLB insider goes scorched earth on Ben Cherington after Pirates' confounding trade deadline

The Pittsburgh Pirates' trade deadline saw the team trade away long-time fan favorites in Ke'Bryan Hayes and David Bednar, a controllable starting pitcher in Bailey Falter, and others, while retaining a trio of veterans on expiring contracts (Andrew Heaney, Isiah Kiner-Falefa, and Tommy Pham). The consensus among Pirates fans is that general manager Ben Cherington botched this trade season horrifically.

That opinion isn't unique to just the Bucco Faithful.

The Pirates' trade deadline was so bad that national media members are starting to get involved in the discourse. The most prominent example of this came from FanSided's MLB insider Robert Murray, who went off on Cherington and the Pirates on a live episode of The Baseball Insiders over the weekend at The National Collectors Convention in Chicago.

"It was horrendous," Murray said of the Pirates' moves leading up to the July 31 deadline. "What were they doing? It felt like an organization that doesn't have a plan by any means. It was flabbergasting."

Cherington somehow managed to get poor returns for some of the players he moved (Bednar, Falter) while also failing to take advantage of the trade value of a pair of key pitchers the club retained (Mitch Keller, Dennis Santana). It truly felt like the Pirates' GM was asleep at the wheel.

Murray was particularly vexed by one move the Pirates did make and another that never came to fruition. The insider referred to the Pirates' end of the Bednar trade—headlined by catching prospect Rafael Flores—as a "joke." The young backstop cruised through Double-A pitching but his early sample at the minors' highest level has produced serious swing-and-miss concerns. He is far from a guarantee to help the Pirates win major league games in 2026 and only slots in at No. 11 on the club's updated prospect rankings, per MLB Pipeline.

Cherington certainly didn't help his own cause by outright admitting that he "had access to players who were ranked higher" but chose this prospect package instead. It's another shameful instance of Cherington thinking and acting like he's smarter than everyone else, and it makes even more damning Murray's revelation that other general managers, executives, and players had absolutely zero idea what he was thinking.

Murray's other issue stemmed from the Pirates' refusal to trade Keller, who surely would have netted the organization a serious package of young hitting talent in a trade while clearing around $60 million off of the team's books. He expressed bewilderment with the team pulling the right-hander off the market entirely when other clubs potentially might have paid Jhoan Duran-like prices for him. Not to mention, the Pirates have No. 5 overall prospect (and No. 2 pitcher) Bubba Chandler waiting in the wings, who could have stepped right into Keller's place in the rotation.

"It was an opportunity that they could have taken advantage of and could have changed [their] team," Murray said. "Move him, add to the farm system, and then you call up Bubba Chandler...It was so obvious, and yet they missed."

MLB insider thinks Ben Cherington's trade deadline may have finally cost him his job with the Pirates

The culmination of all of the confusion and frustration around what Cherington just pulled off may soon come to a head. While that would certainly be bad news for the Pirates' general manager, it would also represent a massive relief to much of the fan base.

"When you can have everybody on the same page about it being that bad, then why is Ben Cherington in place in Pittsburgh?" Murray asked of the team's activity around the trade deadline. "To me, this was the beginning of the end of his tenure in Pittsburgh."

Time will tell if ownership ultimately decides to pull the plug on Cherington after six lackluster seasons. But the clock is ticking for the team to build a competitor around Paul Skenes, and it would be more than fair to question whether Cherington is still the right man for the job. It sure doesn't seem like he's done himself many favors lately, and the baseball world is starting to take notice.