To use the athletic ability of a player you need ball handlers that can push in the open court or players that can throw lobs. The only one in recent memory that could really push was Hart, so frankly, DJJ was probably used about as much as you could use him. He could not create for himself and to be a lob-threat, the Blazers needed ball handlers that consistently throw these. With Dame and CJ quite often calling their own number - DJJ was used as efficiently as he should have, no disrespect to anyone, but DJJ even with his athletic ability was never an efficient primary scorer, so if the question was let Dame or CJ shoot or run sets to free DJJ... Terry went the right way.
Now, DJJ, just like Sharpe, would have thrived better in this year's Blazers team, but that's not because of Terry, it's because the roster had Hart and Winslow.
What we have seen from DJJ is that his TS% has gone up a bit in Chicago, but he plays quite a bit less. The issue, per usual, was roster optimization. The Blazers had to play him a lot more than he deserved to because they did not have any bigger wings - but when they did, they minimized his offensive role as they should have.