This is all pure speculation and if any of this goes down as I suggest, I will be as surprised as any of you. The major point of this speculation is that POSSIBLY what we do may be determined by what another team, picking in the lottery, does. Also, that who we draft totally depends on which free agent we have decided to target and that depends not only on who we want, but who we think we can sign. Many of the free agents I would imagine KP has interest in have been rumored to be difficult to pry away from their existing clubs.
So let's make some assumptions that seem to be true based on the rumors we are hearing.
1). KP would like to upgrade the talent at the PG position. Sergio is likely gone, possibly to NY for the tpe and future considerations. We have had some discussions with Chicago regarding the availability of Hinrich, but the Bulls are hoping for something bigger than Blake and cap space and are waiting to see what else becomes available (hoping for Bosh or Amare but likely to be disappointed). KP views Bayless as a capable backup and is comfortable with Blake being our starting pg next year if that's how it works out. A rookie could replace Sergio and give us options when Blake's contract expires.
2). The other huge need is to add some toughness. A rebounder. A banger to backup LaMarcus. This could be addressed with a lopsided trade, but I haven't heard of many good options. Teams that have this player, don't typically want to give him up. There are several intersting options as free agents, but do the good ones want to come here knowing that they have zero chance of starting or getting big minutes barring injuries. How much can we afford to pay a backup? Can this guy get paid more someplace where he has a larger role.
3.) It seems like we will draft to attempt to satisfy one of the above needs (pg or pf) and then use our cap space to satisfy the need not addressed in the draft. We should be able to get a far better (or at least more ready to help) player with the cap space than in the draft.
So what happens on draft night depends on which free agent you target. This is my list of FA we should be looking at (by position)
SF (You'll notice I didn't list SF as a need in the assumptions I am not buying in to the Turkoglu talk.)
Trevor Ariza- He doesn't really fit a need, but he's a nice young player and somebody needs to compete with the Lakers for his services so he doesn't sign there for a "below-market" deal. We need the Lakers in Luxury tax hell. Liklihood of landing him: slim
Jason Kidd- Obviously great in his prime, but unsure how much he has left. Certainly would not be a long-term answer at pg. Would be expensive. Says he wants to stay in Dallas. I would personally prefer Blake with his outside shooting at this point in their careers. The only upgrade here would be defending the bigger, stronger pg in the league. I think that is offset by his inability to cover the quicker PGs. Liklihood of landing him: average
Ramon Sessions- Young scoring PG who creates easy shots for teammates with his penetration. Fits our window. Could be considered a young Andre Miller (which to me makes him more attractive than Miller). Needs to develop into a better perimeter shooter and a better defender. Is he better for this team than Blake? It depends on what you want to put next to Roy. If you want a PG that sits outside and can hit the open 3, he's not your guy. A little scary that the Bucks can match any offer, but they are on record as planning to avoid the luxury tax. Liklihood of landing him: average to good
Miller, Bibby, Nash etc.- Any one could be a short-term upgrade at a very high cost. I would prefer to keep Blake.
Conley, Hinrich - Definitely options, but we have to have a willing trading partner. I think even if Conley gets traded it will be to another team offering a better package (unless we are willing to give up Rudy and I wouldn't). Liklihood to get Hinrich: average to good
Lamar Odom- Similar to Ariza, make the Lakers pay to keep him. He meets our needs, but wants to be a Laker and I don't see the Lakers letting him go. Liklihood to get him: slim
Brandon Bass- I love his game. He would be great, but if you were him would you come and be LaMarcus' backup? Cuban will pay him. Liklihood to get him: slim
Antonio McDyess- Surprisingly effective at his age and with his injury history. He seems like he would be a nice veteran influence. Just what Nate has been looking for. He will surely have many teams interested in his services. Would you pick the Blazers over other teams if you are looking for a ring? Maybe. Liklihood to get him: average to good
Leon Powe- Very effective player in Boston. When KG went out the Celtics offensive efficiency numbers went up. Powe is no KG, but he is a very solid backup. Would probably be willing to come to Portland as he was a Pac-10 player. Would not be available until after the all-star break, but you may get an injury discount on his salary. Celtics in salary cap hell. Liklihood to get him: good
Chris Anderson- Interesting player. Enjoys his role in Denver. Would have a much smaller role here. Does he fit the culture? I would take him. Liklihood to get him: slim
So summarizing the FA pool of guys that we have a better than average chance of signing: Sessions, McDyess, and Powe. Hinrich is in the mix if we can swing a trade. So what do we do on draft night? Some have suggested it depends on what Memphis does with #2. If they go with Rubio then we go after Conley. I disagree. I think it depends on what Milwaukie does at #10. If they draft a pg, they seem to have interest in Flynn, then it would seem very unlikely that they would match a Blazer offer for Sessions. We draft Pendergraph (or Hansbrough if he falls) at #24. We can continue to negotiate with Chicago for Hinrich. If they won't agree to a deal, Sessions is a real nice fallback.
If, on the other hand, Milwaukie were to decide to go with a big at #10, maybe Earl Clark, we may need to reconsider our plan. That would be a sign to me that they have decided to match any reasonable offer for Sessions. If we go big with our pick and Chicago doesn't play ball for Hinrich... we have limited options to upgrade the PG spot. In that situation I would make an effort to move up to grab Lawson or Maynor and then look to McDyess or Powe as free agents.
Is it possible that what happens at #10 will have a huge impact on what the Blazers decide to do? I don't know, but it's a theory.