With injuries to Brandon Roy and Greg Oden that ended their tenures with the Portland Trail Blazers, the franchise has remained a fringe playoff team.

Damian Lillard was the NBA's Rookie of the Year last season and the Blazers have resisted trading LaMarcus Aldridge for younger players. 

"Paul Allen has never wanted to rebuild," says Neil Olshey. "He does not want to take three steps backward in order to take four steps forward. So we decided we were just going to have one foot in, and one foot out."

Aldridge is now 28, while Nicolas Batum is 25 and Lillard is 23.

"Something like 45 wins is OK with a young roster, starting a bunch of rookie scale guys, and when you have all this cap room in 2015," Olshey said. "But if you're capped out with no flexibility, hovering around 45 wins? That's not acceptable."