In a terrible draft.
To be fair...if I were the Blazers...I might have done that deal and built around Lillard and Batum. Its a bad draft though. So, with 1, 10, and 19...who are you getting in this draft that will give some legitimacy building around Lillard and Batum?
You got your pick of the litter @ #1...so, who do you take...right now, its all bigs...Len (you already have Leonard), Noel (you won't play him much as a rookie). McLemore has slid down (although, he makes the most sense @ #1 for Cleveland, IMO), Oladipo is a reach @ #1, same for Porter.
Then @ #10, mock drafts have the Blazers picking a big. Steven Adams, Big Nog...or a guard...KCP. Then @ 19, you have a slew of players...who knows, but lets say...a role player.
So, for Aldridge, you move on and get say...Nerlens Noel, a guard (KCP, MCW, McCollum), and a role player (I've seen mocks with Shabazz sliding to around 19, so, lets say him on the high end or a Reggie Bullock or another kind of backup role player there)...is that a good deal in this year's draft?
Portland then has a roster of Lillard, Matthews, Batum, Hickson, Leonard, Noel, KCP, Reggie Bullock, and the rest of their bench (Claver, Freeland, et al). I'm not sure you are actually improving the team from a mid-level West Squad. Although, the team is a little deeper and one of the Blazers major issues was their depth.
Eh, now I've talked myself out of it...I probably wouldn't make the deal.
Cleveland has eyed up Aldridge all off-season and would be perfect for them.