that wasn't a risk at all. Portland was in a 'nothing-to-lose' situation and Melo's contract wasn't even guaranteed when signed
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I'm thinking people have a different definition of risk than I do. For me, trading Turner for Bazemore wasn't a risk because Portland was not risking anything. Meyers & Harkless for Whiteside was very little risk, because again, they weren't risking much, and Whiteside's skills were known. Letting Layman and Curry walk was again, small risk. I really don't think risk is very cumulative. 3 or 4 tiny risks don't equal a bigger risk. Mainly, futzing around with the lower end of the rotation isn't much risk. Neither is exchanging role players
the biggest risk Olshey took last summer was betting that better offense and floor spacing was going to offset the loss of perimeter defense and rebounding. But that bet didn't fail because of who he got rid of, it failed because of who bet on...c'mon Neil, really? Bazemore, Hezonja, Tolliver, and injured Gasol? The perimeter defense was gone but the better shooting never showed up. Changing the roster so much wasn't a big risk as much as it was poor execution.
IMO, real risk occurs at a higher level in the rotation, above the average role-players. It happens when you change the core. Perhaps like a Capela for a Covington
Olshey is risk-averse. That's often worked out for him because he seems to be really tuned into the NBA's version of Craig's List. He's always rooting around in the dusty corners of other teams' garages and avoids the man-caves where all the big screen TV's are. The light from those screens is unforgiving and asses are uncovered
I can't recall Olshey ever taking a big risk; nothing even close. Maybe the closest was the Afflalo trade, and that was a failure, and it was still low-level risk. His Batum trade was a bust but circumstances gave him an excuse. Maybe Plumlee for Nurkic, but Plumlee was not a core piece and the primary motivation for that trade was to kick the can of RFA a year or two down the road
personally, I believe Portland has to take a big risk pretty soon otherwise the high water mark of the Dame/CJ team team may very well have been last season. I know many here believe that all Portland needs is just another decent supporting player, or two. But I don't think supporting players alter a team's trajectory