Handlogten's Heros
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Its really easy to see why Vando/KO is appealing to them. They need help with their bigs... they have Grant/Little/GP2 that can pick up some slack on the wings. They also want to keep Sharpe in the rotation. They also know that they don't have the money to bring back Hart. So get Vando who is cheap this year and next (and honestly the real reason is Dame loves Vando) KO can help cover some center/pf minutes and if it works you can keep him... if not you waive him.I don't really see what the deal would be from Portland's POV.
If they're motivated either: a) mainly by money and want to get off of Hart for a longer cost-controlled set of players, I guess I can see that; or b) if they're willing to go all in now and give up a prospect the Jazz like, I guess I could see that.
But I don't much value of them swapping out either Hart or Winslow for Vando/Vando+. Losing their best non-center rebounding/toughness for Vando doesn't seem like much of a benefit, unless they plan on moving Grant to SF and playing Vando and Grant together (not sure that's something I'd recommend, but maybe it can work).