To think the Blazers have a shot at DWill. I know it isn't likely, but from a basketball perspective it might be his best option.
Everyone seems to think that he will choose Dallas (his hometown) and team up with Dirk and Jet to make a championship run. Or he could stay with the Nets and hold on to all that endorsement money he's signed up for.
While the blazers can't offer the endorsements of the NYC or Dallas markets, they can offer a better and longer term basketball opportunity to a young guy who is arguably the best PG in the league.
The Blazers on the other hand, have LA (26), Batum (23), Wes Matthews (25-and a great 2 to pair with DWill) the possibility of a Joel Freeland (25), potential in Elliot Williams(22), 2 lottery picks this year, free agent money to bring in another good piece, and an owner willing to spend (for the moment). While that may not blow your doors off by itself, that is a roster loaded with above average-good-great players that is simply needing a PG to lead it and make it work.
DWill could probably compete sooner in Dallas, but his window will be 1-2 years with the age of that roster. With the Blazers his window is 5+, especially when you consider that most (if not all) of the talent is even younger than DWill the team should get better and better as the years go on.
NJ/Brooklyn does have some young talent, but nothing on par with what the blazers have (thanks for the lottery pick NJ!) For NJ to compete they would need to bring in even more pieces than what they have now while the Blazers have the potential to have the roster filled out now, and DWill is just the piece to turn it into a consistent contender.
Still, Portland has its drawbacks (weather, small market, crazy owner, little stability in the front office) and I don't think DWill should be the only option (Sessions is playing well...if you can pry him from LA)....but they should try...I think they have a pretty good argument.