I don't think our small forward issues are serious, since we're still not sure what we have with Martell coming back from injury, Batum clearly being a promising prospect, and with Outlaw capable of playing minutes at the small forward position as well. Add to that Rudy and Roy's ability to play spot minutes in a pinch, and we'll end up with something that works at the SF with personnel already on the roster

So like 10,000 other posts, this is going to address the point guard position. Sergio has not proven to be a good fit here. He's not a good enough defender, and he never will be. The rest is just window dressing - the shooting, etc could conceivably be improved, but he just doesn't have chops defensively to be successful in Nate's system.  Steve Blake is great for what he gives you - consistency and a facilitator's mindset. He'll be a serviceable backup down the road.

Jerryd Bayless is a combo guard who can create off the dribble, but doesn't have the court vision to turn that creativity into dimes.  This year wasn't an anomaly, I think down the line we'll come to realize KP gave Nate a player who didn't fit a need in the Blazers system.  Perhaps he was thinking he'd eventually fill Jarrett Jack's role as an penetrating energy guy off the bench. And I do think Bayless was the best player available to the Blazers from where they were picking in that draft.  But I don't think he's got a place on this team as currently composed.  He is not a point guard (he wasn't one in college, either), and you don't learn to be a point guard in the NBA if you're not a point guard before you get there.

So we have a starting point guard who's a championship team backup point guard, and two backup point guards who aren't well-suited to this team's needs.  What to do?

Well, we've all heard the old saw about moving Brandon Roy to the point guard position.  This would be making a commitment to half-court basketball all the time, Brandon does not look to push the ball when it's in his hands, he is a deliberate court general when he has the ball.  Blake is a little better, but both of them are not easy fast break point facilitators. Coach McMillan would be ok with the slow pace, he hates turnovers in transition more than he loves uncontested layups.  The problem with this idea is that Brandon clearly isn't interested, in part because constant ball-handling responsibilities wear him out.  If this was ever going to happen, it would have already happened, as McMillan has stated to the press he'd be trying Roy at PG, and the experiment has only been given brief trials over three years, and never sustained.

Similarly, Rudy Fernandez will not play point guard.  It might work if the Blazers ran a triangle-like offense predicated on interchangeability and movement, but the point does have responsibilities for starting and resetting the Blazers offense, and Rudy is better passing the ball off the swing than he is when he's bringing it up, and his handle isn't point guard quality.

We could pick up a veteran point guard. I like Andre Miller, though I sympathize with those who believe he might be about to fall off the age-related productivity cliff and worry about his poor lifetime outside shooting percentage. He is a point guard who can penetrate and make plays, stick to his man on defense (though he's not a top tier defensive player), and fit very well into the Blazers locker room. So to my mind, he'd be one option, though I think there's a good chance he re-signs with Philadelphia.

In terms of free agents, Jason Kidd is not interested in playing for Portland, he's said so himself (through his agent).  Ramon Sessions got a long look from the Blazers brass when they brought him in for pre-draft workouts a couple years ago and they decided he was not what they needed.  I'd be surprised if their opinion has changed.  Mike Bibby is a terrible defensive point guard. Nate McMillan would not be on board with signing him, and I think he'd be right to resist that option.

If Andre Miller is not available or the Blazers decide he's too expensive or too risky, what then are the best options available through the draft or trades?  The Blazers will draft in the 24th spot this year in the first round, and Darren Collison from UCLA,  Curtis Jerrells from Baylor, Tony Douglas from FSU, AJ Price from Uconn, Tyrese Rice from Boston College, and a few second tier foreign point guards are all still projected to be on the board.  Unfortunately, the reason these players are most likely to still be on the board is because it's far from clear they will be successful in the NBA, none of them are likely going to be able to step in anytime soon to help guide a contending NBA team.

That leaves the Blazers in a position where they either need to trade up in the draft or try and pry a quality point guard off another team with players and picks. While Orlando has multiple starting point guards, I think after they (sadly) lose the Boston series, Rafer Alston is the one they let go, and we don't want him. I'm not a Baron Davis or Gilbert Arenas fan in terms of their fit with Portland, and Chris Paul, Deron Williams, Tony Parker, Derrick Rose, Devin Harris, Chauncey Billups, Rodney Stuckey, Rajon Rondo, Russell Westbrook, Jose Calderon, Mike Conley, and DJ Augustin will all be too expensive in terms of what we'd need to give up to get them - if the teams would even entertain trade talks; for many of these guys, they wouldn't. Steve Nash is getting long in the tooth and is a poor defender.

The Bobcats might part with (or not match an offer sheet to) Felton, but his shooting numbers make Andre Miller look good.  Chris Duhon could be available, but it's unclear he's much of an upgrade from Steve Blake. I've seen Nate Robinson's name mentioned here but he's not a point guard. I've also seen a lot of talk about Kirk Hinrich, but it's clear to me that the series with the Celtics proved that he has a lot of value to the Bulls as both a backup point guard and a two guard, and with Gordon's uncertain future with the team they're not going to trade him for a backup point guard or two and small forward (where they've got both Luol Deng and Salmons).

There are a few players on the draft board above where the Blazers pick who might fit the team's need for a quick, steady, creative point guard who can really defend. Ricky Rubio could be a good fit, but since he's a lock for the first two picks, getting him would almost certainly require excessive concessions, something more than just taking on a bad contract and moving a non-core player or two. Depending on how the draft falls out, though, either or both of Ty Lawson and Brandon Jennings may be obtainable for the right price. They're lottery picks, but probably not high enough in the lottery for the picking team to dismiss trading them out of hand.

Each of them has their issues. Lawson has been hurt, but nothing serious that would raise long-term durability worries (unlike, say, Brandon Roy's knees). His three years of collegiate experience at a top tier school would make him the more likely of the two to successfully transition to making an immediate impact in the NBA.  He's a tenacious defender and has a pro's body.  I imagine KP is looking very carefully at the moves available to him to try and land Ty Lawson.

Brandon Jennings is another option, though the year he's spent abroad has made it clear he is not yet ready to start at point guard for a contending NBA team like the Blazers.  He has struggled with his shot selection and his shooting percentages in the European league he's been playing in this past year have been poor as a result.  It would take some time for him to adjust to the NBA. But he's a creative playmaker, a tough defender, and has a good stroke already (unlike, say, Sergio). Also, he's lightning quick, somewhere in the neighborhood of Tony Parker, if not Aaron Brooks.  If the Blazers were able to pick up Jennings, it wouldn't have much immediately impact on their championship prospects for 2009-2010, but it would give them a strong core for most of the next decade.

There are a handful of other guards in the draft that will go before 24, but none of them project to be NBA starting point guards right now (Evans, Holiday, etc), and we have the only combo guard we need as our primary franchise player.

Based on my analysis, if we think our championship window is open this coming season, trying to sign Andre Miller may be enough to get us there, but if the plan is still to build for the next decade, trying to move up in the draft to get Lawson (best uncrazy case scenario) or Jennings is what I'm hoping the Blazers organization is working hard to do right now.