when has he ever "swung for the fences"? He's a master at dumpster diving, and pretty decent at drafting perimeter players. But swinging for the fences requires actually making a core player or a high lottery pick available...taking a big risk for the chance of an even bigger reward. By all reports, when PG13 was on the trade block, Olshey made CJ untouchable. That's the opposite of swinging for the fences. Olshey always bunts
"contender land again"....? the last time they were a contender was when Pippen was on the team and they had the biggest 4th quarter choke in Blazer history. Trading Whiteside or Bazemore isn't going to elevate a team with the 4th worst record into being a contender
the problem is that fucking around with the back end of the roster isn't going to make Portland a contender. Making changes in rotation players 5-9 almost never alters the trajectory in a plus direction. It can however crater the trajectory as we've seen from Olshey's past summer
if Portland wants to dynamically change the trajectory, they will actually have to swing for the fences. Take a big damn risk. That's only going to happen if the GM can put aside his irrational biases for 'his guys', and move a core piece. CJ is just about the only candidate for this, but his value is probably pretty low with the season he's having and the 5yr/157M he's owed.