Only way I see Winslow developing is by trading Dragic and making him our official point-forward where he does the bulk of the ball handling because that's what he does best on offense IMO. His shooting doesn't fit the "stand around the 3pt line and wait for the ball" game he's been stuck in during his stay.
J-Rich to me should have been developed to be Dragic's backup at PG. I guess TJ's presence made them shift him to SG and now to SF but he has no business playing SF as frail as he is. He hustles but he's out of position.
And as I mentioned earlier I would love for Spo to implement some aspects of the TRIANGLE OFFENSE into this squad. We have the personnel to run some sets like that except the focal point of the triangle, Whiteside, will have to learn to be a better passer. But I think with him and Olynyk on the floor together it can work
This was never going to happen, Rich don't have the ball skills or the vision. Offense stutters when he's running point. I said 2 years ago we were going to have to make a decision on Rich/TJ because they play the same position, but we went against the grain and further complicated matters with addition of Waiters, Ellington, and Rodney who is another natural 2, not a SF. At least two of the bolded are going to have to get traded to clear up this rut and we can get guys back to playing their best position.