Now is the perfect time for the Trail Blazers to trade Damian Lillard and start over

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How long are the Portland Trail Blazers and Damian Lillard going to keep doing this thing?

What thing, you ask? You know the thing I’m talking about. The thing where Lillard expresses his desire for Portland to build a contender around him, Portland fails to build a contender around him, another season of his prime is wasted in Portland and Lillard’s name is mentioned in trade rumors before he states his intention to to win in Portland again. Rinse, repeat.

At some point, one of the sides has to decide it’s not worth it anymore. And if I may suggest, in the year 2023, ahead of Thursday’s NBA Draft, that side should be the Trail Blazers. They should just make the decision for Lillard. Trade him and start rebuilding.

RELATED: 6 wild Damian Lillard trades, according to Trade Machine

In past years, when the Blazers were more competitive, you could forgive them for running it back with Lillard, even if they weren’t legitimate title contenders. Lillard is an all-time great player who at least kept them relevant.

But going on 33 years old this summer, he’s on the back end of his prime and the team still doesn’t appear close to contending for anything. They missed the playoffs altogether last season, and the blessing in disguise was that it gave them the rare opportunity to draft Lillard’s successor, if reports about Scoot Henderson falling to No. 3 turn out true — though there are reasons to be skeptical.

If that happens, the Blazers should use the moment as an opportunity to split with their all-time leading scorer and reset the roster around a new point guard. Especially if they don’t plan on trading the pick.

As good as Henderson potentially is, he doesn’t fit Lillard’s timeline — nor does any other rookie. The assets Portland could get in return for Lillard would put them on a better path than the floundering state they’re in now. And Lillard could potentially go to a team more equipped to contend now.

If there’s anything to be learned from the Wizards’ trade of Bradley Beal, the Blazers don’t want to wait until it’s too late. It’s never easy to say goodbye, but the No. 3 pick gives them the perfect opportunity to do it now.

Like Scoot Henderson, another point guard expected to hear his name called early Thursday is Villanova’s Cam Whitmore.

But while some mock drafts have him coming off the board soon after the expected first three names, our guy Bryan Kalbrosky explained why he could potentially fall in the draft, citing a reports from Bleacher Report’s Jonathan Wasserman about concerns over Whitmore’s medicals and from The Athletic’s Seth Davis questioning his feel for the game.

Still, the upside is undeniable.

“You never want to see potentially poor medical information about a player.

But the upside is still strong for Whitmore, who measured with a 40.5-inch max vertical during the 2023 NBA Draft Combine and tested well in drills for speed and agility as well.

Whitmore uses that to attack the basket and he scored 0.76 points per touch on drives, per Stats Perform, which ranked as the best among projected first-rounders.”

Hopefully, Whitmore’s potential shines through at the next level and makes everyone forget about the concerns being expressed before the draft. It’ll be interesting to see which city he and the other prospects land Thursday to start those journeys.

RELATED: 2023 NBA Mock Draft 9.0

Shootaround

— Kendrick Perkins embarrassingly fell for a fake tweet about Jonathan Kuminga’s height

— Brandon Miller had fans so confused when he said Paul George was his basketball GOAT

— Victor Wembanyama will wow fans with his ‘enlightened’ mindfulness off the court

— 6 NBA Draft lottery teams that can make the playoffs by nailing their picks