I think Lee did what was in his best interest and so did the Blazers. All in all I'm kind of glad things turned out the way they did; this team was hurting in the worst way when it came to another facilitator and was exposed badly as a very one-dimensional team in the playoffs.
Lee signing with the Blazers would have led to more moves IMO.
Signing Miller with their cap space was low on the Blazers priority list because it doesn't give the team as many options with the remaining players.
See: Sign Miller (as we have done),
Now we have Miller, Blake and Bayless at the point. We could look to move Blake, except that Bayless was a disaster at the point during summer league - not ready to be a backup. As well, Blake is the best 3pt shooter. Moving him, considering his modest trade value, seems likely to be unhelpful.
Now we have Aldridge, Outlaw, Howard and Cunningham at the 4 spot. I don't want to see a lot of Howard and Cunningham. We have no other options at the 4 spot, so trading Outlaw is not a good idea right now.
So, we are "stuck" with Blake and Outlaw, both in contract years, who won't have much if any trade value after this summer.
We have Oden and Joel at center. Can't trade Joel as the next best true big on the roster is Howard.
Bayless has little trade value until he proves he belongs. Webster has no value until he proves he is worth his contract. Roy/Aldridge/Oden are untouchable.
That leaves Rudy as the player who A) has decent trade value and B) the Blazers could work around losing. Rudy and Travis for backup PF? Rudy and Travis for a young PG? The downside of this is that the Blazers like Rudy, he is on a cheap contract for 3 more years, and if he blows up this year his trade value could skyrocket. They are real reluctant to make this move.
Now, if either Milsap or Lee were obtained:
Blazers are thin at PG.
Blazers have Lee (or Milsap), Aldridge, Oden, Joel and Travis as players that deserve big minutes. Seems bad. It is not.
Joel is coming off his best season and has good trade value as a starting caliber Center who won't rock any team's boat by taking shots from an established star.
So, now the Blazers have Joel as trade bait. Outlaw as well as a big rotation of Aldridge/Oden/Lee (or Milsap) is what would work well anyway. Blake if PGs are coming back. Rudy for a star. That is a lot for KP to work with.
Miller was still floating out there. A sign and trade with Philly might have worked out. So, Miller AND Lee was within easy reach, with the possibility for even more.
Lee screwed it up because he couldn't see into the future and couldn't figure out the obvious (ie, that Outlaw and Joel would be gone within one year if he came on board).