Every NBA team’s biggest question mark for the 2021-22 season

Portland Trail Blazers: Will Damian Lillard ask for a trade?

Lillard has been the perfect face of the franchise during his entire tenure in Portland. Credit the Trailblazers for compensating him as such, but the team’s front office can be justly criticized for their failure to build a legitimate title contender around their star point guard.

It’s logical to believe that Lillard will start to ask serious questions about his long-term future if Portland gets off to a shaky start this season. He’s self-aware enough to know that his career is starting to reach the end of his prime. If he wants to win a title, it’s likely in his best interest to ask for a trade ahead of this seasons’ deadline.

The problem for Portland is that getting equal value for Lillard will be nearly impossible. He’s an All-NBA level player with a penchant for playing his best basketball when the stakes are at their highest. Getting a collection of draft picks for a player of his caliber is going to feel empty for the Trailblazers’ passionate fan base.

Then again, it might be time for Portland to hit the reset button. They could see moving CJ McCollum as a nice way to placate Lillard, but that won’t bring back enough to truly transform the roster. The Blazers are headed towards an awkward showdown with Lillard this year.