" This is where Klutch Sports comes into play. After bidding against himself to overpay multiple players (i.e. McCollum, Meyers Leonard, and Maurice Harkless), Olshey seems to have come to his senses in the last couple years. Most notably, Jusuf Nurkic signed a team-friendly deal in 2018.
Not so coincidentally, Nurkic has since signed with Klutch. Presumably based on their reputation for being extremely aggressive and player friendly in negotiations. The tl;dr here is that Rich Paul and co. aren’t going to accept a low-ball offer on Trent’s behalf. This, combined with Trent’s pending RFA status during a slight salary cap depression, suggests that it will be difficult for the two sides to find a middle ground during the offseason."
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I don't think we know if Olshey has come to his senses about bidding against himself. The Nurkic contract came at a time when only 3 teams had cap-space above the MLE and all three teams had good centers. All we really know it that when Olshey has big cap-space or one of his favorite players is due an extension he makes bad decisions. When the market is slanted heavily in his favor, and there's limited league-wide cap-space, he makes good decisions.
Nurkic just had terrible timing for his free agency.
if Trent has confidence in his own abilities and his potential for improvement, he won't be very enthusiastic about signing a contract of less than 13M/year when he'd be eligible for a max of 30M/year 7 months from now; especially considering he'd be signing as CJ's backup
Olshey is going to be tested over the next couple of seasons. Not only is Trent eligible for an extension, Zach is too
Portland free agents next July:
Zach
Trent
Kanter
Giles
free agents July 2022:
Nurkic (isn't he eligible for an extension right now too?)
Covington
Hood
Jones
Simons
lots of loose ends. And in 2022/23 Dame + CJ will combine for 80.6M in salary which could be over 70% of the salary cap. The following year they get 86.5M