I think the absolute biggest way I can criticize Cherington is look at what he did with what he inherited from the 2019 Pirates. Even though the 2019 Pirates had that awful end of season collapse that cost Hurdle and Huntington their jobs, that team had some decent talent and was only 1 year removed from an 82 win season. That team had legitimate trade chips between Bell, Frazier, Marte, Taillon and Musgrove, plus they had Reynolds and Newman as MLB proven young guys and Keller and Hayes as guys who would be ready soon. They also had Cruz as a top prospect in the system already. The team Cherington inherited had pieces, he wasn't coming into a graveyard of a team.
What did he get for the trade chips on that 2019 team? Marte was traded for Peguero and Malone, today Peguero looks like a bench piece with no standout traits and Malone ended up a bust. Taillon was traded for Yajure, Contreras, CSN and Escotto, where they only got 1 mediocre season out of Contreras (who they then lost for nothing) and everyone else was a bust. Bell was traded for Yean and Crowe, where Yean ended up a bust and Crowe was a horrendous MLB pitcher for the Pirates. Frazier was traded for Suwinski, Marcano and Miliano, where they got 1 good season out of Suwinski (who they likely end up moving on from this off-season) and everyone else was a bust. Marcano even later got banned from the MLB entirely for gambling.
Musgrove is the only guy that the Pirates actually got value for, but that value was 95% Bednar and hopes with Endy as a prospect. What value does a great closer even have to a 100 loss team, anyway? If Cherington was a smart GM, he would have sold high on Bednar, but his other trades make me believe he would have just botched that deal as well.
No one can deny that this team is absolutely crippled by Nutting, that's a factual statement. But you simply cannot look at Cherington's tenure as the Pirates GM as anything but a major failure with what he inherited versus what they have now. Even though the records won't show this, I think this team is simply in a worse spot now than they were in 2019. If that doesn't paint how major of a failure his tenure has been, I don't know what will.