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Why Trading Damian Lillard is the Right Move for the Trail Blazers

Nobody wants to do it, but that doesn’t make it wrong.

NBA: Milwaukee Bucks at Portland Trail Blazers Soobum Im-USA TODAY Sports

The Portland Trail Blazers are facing all sorts of decisions as the Summer of 2022 approaches, but the most important centers around franchise superstar Damian Lillard. For a decade, Lillard has lifted the Blazers out of sub-optimal situations, making them relevant on the national stage, bringing hope to the franchise and its fans. This season, he hasn’t been able to do so in the same way. What the future holds is anyone’s guess.

Since the Blazers have already traded away half of their upper rotation, the next logical question is what they’ll do with Dame. That’s the subject of today’s Blazer’s Edge Mailbag.


[TNT analyst Charles] Barkley said the Blazers need to trade Dame now. Do you agree? Would you be ok with that? I know it’s an overdone discussion but I want to hear your opinion.

(Please say no!)


Well, how’s this?

No...but also kind of yes.

If you read the article we published earlier today, you’ll understand that Portland’s motivation this year has been to jettison “weighty” contracts, off-loading cap-clogging players who, while good, weren’t bringing the franchise any closer to a championship (or any farther down the road, for now). They sacrificed talent—CJ McCollum, Norman Powell, et al.—in order to earn flexibility. They’re not better, but at least they have prospects of moving now that they’re not overburdened and losing momentum by the day.

Damian Lillard does not belong in this category. He is a unique player, one of only a few who singlehandedly altered the course of the franchise. He’s an All-Star, an All-NBA player, a future Hall-of-Famer, named one of the NBA’s 75 Best. He is not one of those “weighty” players that the Blazers would move for future flexibility alone. The chances of them finding anything comparable are infinitesimal. When Lillard leaves, an era will end. The only word to describe the Blazers at that point will be, “Rebooting”. That wasn’t true of McCollum, Powell, or anyone else the team just traded away.

We can say this because of Lillard’s proven track record and his overwhelming talent. Those preclude him from ever being designated, “A player you have to get rid of,” in the abstract.

Up until this point, nothing has interfered with that narrative. Before this season, we had zero pieces of evidence that anything would change.

Three developments are calling those assumptions into question right now.

  • Lillard is getting older. He’ll be 32 next season.
  • Injuries have caught up with him, and apparently they’ve been chronic.
  • He’s eligible for a $100 million contract extension, which would kick in when he’s in his mid-30’s.

Note the changing time frame lens. We’re not looking at track record and proven accomplishments anymore. We’re looking at current production (he’s not playing because of injury) and future forecasts (he’s getting older). This is the first time these streams have converged in the same place, at the same time, with this player. Add in the fact that Portland is no longer in serious contention with or without Lillard—and that $50 million per year is a LOT of money, in cap space terms and normal finances both—and these issues not only have legs, they have running shorts on.

Lillard is not an uncomfortably weighty player on Portland’s roster now. If age eats away at his game or injuries persist, particularly in the face of his generational-star salary, he could easily become one. If that happens, his weight will equal that of all the players the Blazers just traded away, combined. In essence, they’ll be right back to the bad situation they just spent all their talent getting out of.

This is the dilemma in which the Blazers find themselves. It’s not a pretty one.

I am not Joe Cronin. I am not Jody Allen. I don’t have to make this decision, and I’m glad of that.

We have no particular access to the mindset or priorities of the franchise: winning, remaining profitable, preparing for sale, or just weathering the storm.

We do know the following:

1. Age is an inescapable reality. As former players are fond of reminding us, Father Time is undefeated. This does not mean that Lillard’s production will collapse tomorrow. Chris Paul is a living testimony that life after 30, even after 35, exists for NBA point guards. But even Paul is not the same player at 36 that he was at 26. And for every story like his, there are multiple dozens of players who didn’t make it past their 33rd birthday while maintaining their customary production.

2. Injuries increase with age. Nobody knows right now what form Lillard will return to, or for how long.

3. The Blazers cannot pretend to be in contention for an NBA title. They are a low-level team. If they’re going to be anything but, they have to show it, not just hope for it.

4. Even if the Blazers were to trade Lillard, they’d not be able to fill his salary slot with anyone comparable. Saying, “We have $50 million in cap space!” is one thing. Luring a player worth spending that money on is another. There’s no reason to believe Portland can.

5. That impending extension looks huge already. It’s going to look enormous when Lillard is 35, franchise-warping if he can’t produce at a high level then.

Combine these, and you’ll understand the murky, middle-ground swamp the Blazers and Lillard are slogging through right now.

If Lillard were in his mid-20’s, Portland could build a whole new generation around him. He might have reason to believe that he could lead them to a title.

If Lillard remained perfectly healthy, the Blazers would have less reason to worry about diminishing value as he ages. They could hedge their bets, keeping him now and trading him later.

If Lillard were replaceable, Portland might be able to craft a Plan B that left his position intact, figuring they would fill it with another player should life with him not work out.

If Lillard cost less, the opportunity cost of retaining him would be more bearable.

None of these things are true. Instead of being able to settle on a firm plan and a backup, the Blazers are forced to put in all their chips on a draw. The only question is what they’re drawing to: keeping Lillard and trying to build a contender now or trading him for future assets and trying to rebuild for the future?

There’s no way to make this decision with certainty. Parsing through the factors, some are more certain than others.

Lillard’s age, contract, and talent are undeniable.

Lillard’s injuries, future production, and Portland’s prognosis as a team are speculative.

Two items on the “certain” list argue for trading him now. The third—his talent—could be affected by the items on the “uncertain” list...either whether he still has it or how much it matters.

And this is where we end up. Every reason to keep Lillard lies in the past or with his present value to the franchise. Everything future-related either argues for trading him or isn’t sure. Sadly, the Blazers have to play all of their remaining years in the future, not in the past or present.

The best-case scenario going forward is Lillard spending his career in Portland, happy, relatively healthy, and productive. Even if that happens, we can’t, at this point, forecast the Blazers winning a championship with him. They didn’t give him enough support over the last decade. They have even less to give now.

The worst-case scenario is Lillard spending his career in Portland either injured or unable to produce at the level he has in the past. In that case, he becomes an all-but-untradeable symbol of a bygone era whose contract makes it difficult to move into the new one.

That’s why, in the end, the smart move is probably trading Lillard now, acknowledging that Portland will never, ever replace him, but that they’ll not be able to make best use of him either and can’t afford to absorb the risk of trying.

This is exactly where Barkley is coming from. Lillard’s value will never be higher than it is right now. He’s one injury or bad half-season away from becoming a difficult trade instead of an enticing one. Portland may not be able to wait and see, simply because the rest of the league is seeing too.

Lillard has enormous value to any team that’s trying to win a title now, who can also absorb the risk of getting a less-than-optimal version of the superstar should that transpire. He needs a team where “good” Lillard (as opposed to great) can still lead a team into contention. He needs a team that isn’t as bound to the salary cap or future assets to rebuild.

Barkley is (probably accurately) forecasting that Lillard, his new team, and the Blazers would all be better off in a good trade scenario than they are right now. He’s playing the percentages in saying that. That’s what you’re supposed to do.

That’s what the team should do.

The problem is, it hurts. It hurts for everything Lillard has been. It hurts because of everything he’ll still do. The comforting move, the hearfelt move, is to keep him in Portland forever.

I feel both impulses myself. My big question is, “Would keeping Lillard be right? And for whom?”

I’ll be honest. I’m not sure it’s the best thing for Dame. He needs the chance to become everything he can be, which includes NBA Champion. I wish that could happen in Portland. Even with the league wide open now, I don’t think anyone can plot a route from here to there in the next four years.

I’m not sure it’s the best thing for the team either. Signing that extension based on past work, with no guarantee of future relevance, is a backwards move. Mind you, I think they should give it to him. He’ll get it anywhere he goes. But they would do so knowing they’re going to trade him, not keep him.

In the end, outside of that desperate corner of my heart that wants Lillard here for life, I can’t find a lock-solid certain reason to keep him that matters. I can find at least a couple things that aren’t going to improve if he does stay, and a couple of others that could go less than optimally.

That’s why, even acknowledging Lillard’s unique place in franchise history, Portland should move him while they have the chance. It’s not the kind of thing you say in the present, in the heat of the moment, but looking back two decades later, all parties involved will probably be able to admit it was the right thing to do for everyone, including Dame.

Barkley was dead wrong that moving Lillard is an automatic decision, or even a good one. Those words don’t fit when players of Lillard’s caliber are involved. No matter the return or logic, rebuilding doesn’t hold anything near the equity that Lillard does. But Barkley is right that the Blazers are probably going to have to make that move anyway. If they do, they need to do it at the time that gives Lillard the best chance to succeed and themselves as much return as possible. That time isn’t two years down the road. It’s now.

Thanks for your question! You can always send yours to and we’ll try to answer!