So far in a little over a year it appears Cronin has drafted a player with superstar potential, something Olshey didn't do (he doesn't get credit for Dame). He brought in Grant for one first round pick. Grant is probably better than any player Olshey traded for in Portland, despite Olshey having made multiple trades with two first round picks. Cronin has yet to let an all-star walk for nothing or given up 60% of the starting lineup of a playof team for nothing.
Olshey was dealt a much better hand than Cronin. He was given a better roster, multiple all-stars, and had an owner that was passionate about winning. Cronin hasn't proved to be good at his job, but he's already checked some major boxes Olshey couldn't.