Right now, which team has screwed itself the most, to the point of having no realistic shot of a championship in the near / medium future?
I'm going with the Phoenix Suns. As far out as 2014, they have around $30 million committed to four players: Gortat, Frye, Dudley, and Childress. They have no elite young players (I don't consider Gortat, Dragic, or Lopez as elite, and outside of an aging Steve Nash, they don't really have any great trade chips.
It's going to be very, very tough for the Suns to get better in the next three years, or to set themselves up beyond that. There are plenty of other contenders for the title, but in terms of "wrecked long-term cap space" + "lack of young players", I think the Suns may be the worst.For that, they get my title of "most hopeless franchise".
Other contenders: Milwaukee (terrible cap situation, but some decent prospects), Golden State (ditto), Detroit, Toronto