Some of that has to do with being Dames Buddy. But, also we probably couldn't get a star level player back in a trade for CJ if you think about. (Though it seemed we could trade him for Harden, but Hou was hard up...a special circumstance.)
The only way to get another star is probably through FA and none will come here. Blazers seem to be fucked if they do and fucked if they don't.
Olshey will be forced to trade CJ now and we might not like the results.
First - No team, outside of a few select teams (LAL, Mia, etc), gets a star player through FA. It's a reality of supply/demand. The majority of teams feel that way.
Secondly - there were MULTIPLE opportunities to trade CJ for an upgrade in the last 5+ years. Some of the more significant missed opportunities are:
+ PG13 traded from Indiana for Oladipo & Sabonis (Olshey wasn't willing to include CJ)
+ Jimmy Butler traded from Chicago for Dunn, LaVine, & Markkanen (Olshey wasn't willing to include CJ)
+ Jimmy Bulter traded from Minny for Bayless, RoCo, Saric, & Second Rndr (Olshey wasn't willing to include CJ)
+ Kawhi traded from Spurs for DeRozan, Poltl & Pick (Olshey wasn't willing to include CJ)
However, at this point - I'm more of an advocate to trade CJ for a comparable talent (Christian Wood) who has a salary that would allow Portland significantly more flexibility (bringing in a backup PG using a TPE).
