I'm sure Portland would be willing to trade Henderson, but the Cavs would really only need him if they don't re-sign Smith or if they experience a significant backcourt injury, since he is pretty much just a SG. I agree he is a guy to watch. .
Thanks for your comments. Well in my point Henderson can be a decent get for backup SF. He played 18% of his time on SF last season, and the production at that position was decent although not as good as SG. His production on SF is between MKG and Lance, outperforming the opponents in PER:
http://www.82games.com/1415/14CHA7.HTM#bypos
JR Smith was outperformed in PER by opponents on SF:
http://www.82games.com/1415/14CLE8.HTM#bypos
Surprisingly, he played good clutch time. But Henderson is not a typical wing player because he cannot shoot at wing (arc) but rather at corners, so in some plays we used much often like Horns, he'll not be a right person to set pick for our guard.
http://www.atthehive.com/2015/5/28/8675531/2014-2015-report-card-gerald-henderson-Charlotte-hornets
But trading the 2018 pick is tough because without it the Cavs' remaining trade assets are virtually nil.
This is also one thing I'm struggled with. Frankly speaking I think Henderson is good but not that much comparing to the 1st round, considering his potential role. But despite the 1st round, the only trade assets we remain are right to Osman, and 2019 2nd round pick (lesser of Lakers' and Timberwolves'), which I believe will not be even close to potential bidders.
Good thing is that right after drafts in 2016 summer, when we probably have sent out our 2016 1st round to Celtics, our 2020 1st round pick (with protection) becomes tradeable even if we have spent our 2018 one this season, making us another trading asset in the future. (Reason that we cannot do that in this season is because our 2018 pick can be realized as late as 2020 at this point, due to the uncertainty on 2016 pick which is protected, so 7 year rule prevents us from sending out 2020 pick at this point).
Unless they experience an unexpected collapse, I don't see why the Wizards would trade Dudley or Anderson, whom they view as key bench guys. Plus Dudley is hurt right now.
Reason that I think either Dudley or Anderson could be spendable is that Wizards have too much depth at wings. Porter, Dudley, Oubre, Beal, Neal, Anderson. One or two of them will struggle for playing time eventually as I believe. Then in the coming summer as they need to set aside space to attract Durant, at least early bird/non-bird right for one of them will be given up. But after all, I agree that all depends on the ranking of Wizards at that point.