The Blazers' position of most dire need, obviously, is point guard. Raymond Felton was a disaster, and is gone. Jamal Crawford isn't a PG, and needs a team with a strong locker room culture to thrive regardless. He's gone. Nolan Smith hasn't yet shown he's an NBA player (he's played well enough as a rookie to get another year, but he looks like a backup at best). Johnny Flynn is definitely a backup at best, and a mediocre one at that.
Unlike the center position, where you can deploy a power forward or big white stiff in a pinch and get away with it, teams absolutely require a primary ballhandler and distributor. You can shirk at the PG position if you have skilled passers and ballhandlers at the wing (Brandon Roy, for example); but the Blazers don't have that either--both Wes and Batum are far better off the ball than on it.
So Portland needs a point guard.
There's one young All-Star caliber point guard in the free agent crop--Deron Williams. It's widely assumed that he has no desire whatsoever to play in Portland, so we won't discuss him further. The draft is weak on PGs--there are two prospects at the position who may fall into the lottery, but no "can't miss" players like a Rose or a Paul.
Assuming DW is beyond our reach, the Blazers could play this in several ways:
Combining approaches may be worthwhile as well--the Blazers need more than just a starter (I'm not comfortable with Nolan or Flynn as the primary backup, either). Were the Blazers to acquire a Steve Nash, he's only got a few years left, so acquiring and grooming his successor might not be a bad idea--and the Blazers could pair him with Lillard or Marshall. The 2013 crop doesn't look very promsing either--there's no outstanding PG prospect among the incoming NCAA freshman class, if DraftExpress is to be believed. OTOH, there's a lot of college ball to be played between now and then.
The past seven years, since Damon Stoudamire left, the PG position for the Blazers appears to have been cursed. I've joked before is that the failure to draft Chris Paul was like Hogwarts' "failure" to hire Voldemort as the DADA teacher. Another often-suggested theory was that Nate McMillan was too hard on the position (or preferred players similar to himself)--that said, none of the PGs who have left Portland have gotten significantly better elsewhere. The most likely scenario is that the Blazers have scouted poorly at the position--a few "tweeners" have gotten looks over the years, though a tweener makes sense if you plan to pair him with Brandon Roy. With the current roster, the Blazers need a multi-way threat at the point, someone who is both credible as a passer and as a scorer.
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