I was on the Olshey bandwagon for a bit, early on, until I wasn't. In retrospect, he clearly was a mediocre GM. Unable to ever surround Dame with high caliber talent, he seemed content to create a middling team of Aminus and Norman Powells. There was some tough luck for sure. Oden of course. Lamarcus bolting. And that team with Batum, Rolo, and Dame was super talented and fun, but Wes blowing his Achilles ended that. Looking at the current roster, what say you? Dame: He "drafted" Dame, but me thinks that was in the works long before he showed up and took credit for it. CJ: His optimum "sell by" date came and went. Olshey was too in love with his own draft pick. Nurk: He got lucky with this trade, that's what I say. Simons: A solid pick, especially late in the draft. Little: A fine pick. Could he spot talent in the draft? Definitely. Could he trade to save his life? Definitely not. Was he a condescending prick? Most definitely. Won't ever be missed, and probably will never work in the NBA again. The way they unceremoniously drove him out of town smells of him pissing off the wrong person one time too many.
Also for all his supposed car salesman skills, he was a shit negotiator and couldn’t sign a decent free agent to save his life.
I still maintain that I think Olshey was probably one of the most “blacklisted” GM’s around the league because of his BS tactics which other GM’s probably caught on to quickly. They probably let Olshey’s calls go to voicemail.
FWIW I ran into Olshey in person once. Wouldn’t say he was rude. I basically just wished him good luck with the game that night and he told me thank you.