Jay Bennett was a talented guy, no doubt.
But honestly I think his biggest contributions to Wilco are confined to Summerteeth. That’s basically the album where he and Tweedy just got nuts in the studio and crafted one of the beautiful melancholy pop albums ever.
Yes he was there for the early sessions of Yankee Hotel Foxtrot, but if you listen to the demos vs. what ended up on the album, the end product was something that was largely shaped by Jeff Tweedy and Jim O’Rourke. Then of course Bennett was gone for A Ghost is Born, which is brilliant in its own right, IMO.
So yeah, Bennett definitely put his mark on Wilco in their most creative years, but I’ve just never bought into the myth that he was “co-responsible” for their creative peak, as many Wilco fans seem to think. He was a cog, just like all of the other cogs that made it work, but outside of Summerteeth, I don’t think you could say that he had any more contributions than any of the other non-Tweedy pieces.