Maybe if KP could have gotten over his infatuation with his stable of drafted players and been willing to make an unbalanced trade (without just offering garbage and expirings or cap room) then that cap space might have been a useful asset, but instead KP convinced himself that he could sell Portland to Hedo. When that failed he just started flailing trying to make a splash (chasing David Lee, etc.) and got (somewhat) lucky when Andre Miller practically begged him to sign him.
With Olshey, he knew this FA crop wasn't great and loaded with a lot of RFAs, so he went hard after the one guy he thought could be a difference maker and when that didn't work he got the best SF free agent on the market for a slight overpay. I get the feeling Olshey understands that trades are going to be the way forward, and having some cap room next summer might help facilitate a winning play.