Portland Trail Blazers desperately need to trade Damian Lillard, no matter the cost

I’m declaring a state of emergency in the Portland Trail Blazers organization and assuming emergency powers accordingly. I have appointed myself Offseason Strategy Consultant and have prepared the following report on the not-at-all-rapidly unfolding Damian Lillard fiasco. Please enjoy.

If I walked out of Powell’s Books in Portland, Oregon – fresh off of reading all one million of their books – onto West Burnside Street and asked the first 10 people I ran into who they wanted to win the 2024 NBA Finals, what do you think they would say?

I’d say probably 8-to-9 people would say “The Portland Trail Blazers,” but I wouldn’t write off a tourist or two from a different basketball city, seeing as Powell’s is a pretty hot tourist spot. Maybe someone would roll their eyes, put their tongue in their cheek, and say “The Seattle Supersonics” just to mess with me

Do you know what answer I don’t think I’d get? “Damian Lillard.”

That is because – contrary to some of the undertones of the prevailing discussion surrounding him – Lillard is not a basketball team. He is a point guard, one that has become the centerpiece of one of the more moronic debates in the NBA today.

Damian Lillard and seven important questions

I’ll try to summarize it in seven questions:

Does Lillard want to be traded? Should Lillard want to be traded? Where does he want to go? Why hasn’t he already been traded? Isn’t he like 32 already? Would Lillard prefer the Trail Blazers build around him instead? Why did they draft Scoot Henderson?

And here are the answers: maybe, yes, Miami, ticket sales, he turns 33 in July, probably, because it was the right move.

I’d say that’s a solid crash course in Damian Lillard Studies 101. Yes, this will be on the test. But I actually don’t care about any of that whatsoever, because the debate surrounding Lillard is missing what is by far the most important question:

Should the Trail Blazers just trade him, irrespective of his wishes? Yes, they should.

Why, you may ask? Because they have to. Building around Lillard at this stage has cratered below unlikely, and is now careening towards downright impossible. This team is noncompetitive, has a dicey financial profile, and a timeline so confusing it might as well be Pulp Fiction. And there is exactly one way to fix it: trade Lillard now, while his value is at the highest it will ever be at.

The saga of Lillard as the franchise cornerstone has hit a wall. The last four years have netted three total playoff games won, and last season saw the Blazers shut down their star in order to tank for a better draft pick. And every year since 2015, I’ve heard the same questions: how does Lillard feel about all this?

But this saga should no longer be about him. The Lillard-Blazers are noncompetitive, and their two most promising young players – Shaedon Sharpe and Scoot Henderson – both play his position and have a combined age of 39 years. The rest of the team is a mess, and nothing fits a Lillard-based timeline in a Western Conference about to be brutalized by the Denver Nuggets for the foreseeable future.

But never fear. I – officially Offseason Strategy Consultant – have formulated a plan to convince them to trade the man. I’d tell Lillard to please step out of the room and simply ask the Blazers’ ownership, general manager, and coach if they still believe the goal of basketball is to win a championship. If they answer yes, I’ll let them in on reasons two through a million why they have to trade Lillard to do so.

Every NBA team’s offseason needs to be fundamentally dictated by a simple assessment of strength: can this roster reasonably compete in a seven-game series with the two best teams in the conference? In the East that’s Milwaukee and Boston, and in the West it’s Denver and Phoenix. If the answer to that question is no, then it’s time to figure out how to do that.

I’ll reserve judgment on the Suns- whose financial decision-making fundamentally confuses me – but there is no world, galaxy, or universe where the Blazers can compete with the Nuggets in a playoff series, as the roster is not built for playoff success.

Their guards can’t play defense, their wings are all specialists who struggle with their specialties, and their bigs do not approach the quality needed to hang with the West’s premier interior scorers. All this smells distinctly like a rebuild, but you wouldn’t know it by auditing the Blazers’ books.

What is a rebuilding team?

Here are the components of a rebuilding team: tons of young players, stockpiled draft picks, and long-term financial flexibility enabled by taking on bad or expiring contracts since the goal is to win later. Upon reviewing the Blazers’ future assets, this Offseason Strategy Consultant is positively appalled. Sharpe and Henderson, along with Anfernee Simons, are the current corps of “young players” to develop, all inconveniently playing the same position. But that’s at least okay.

But here’s what’s going to happen if the Blazers do not trade Lillard. Jerami Grant – a pretty good 29-year-old forward who must just be Lillard’s best friend – will get paid somewhere in the neighborhood of $120 million over the next 4 years. During that same stretch, Lillard will make just under $217 million, a number so large that I had to do a double-take when I added it all up.

Grant and Lillard can form the core of a solid play-in team, and could maybe get further if Grant was the third guy behind a second star. Add a solid supporting cast and the sky is the limit. Here’s the issue with that: If Grant is extended, he and Lillard will take up two-thirds of the Blazers’ total cap room, as well as over 50 percent of the luxury tax limit.

You don’t need a degree in Sportscanomics to know that those numbers are pure lunacy. Worse still is that with that core might accidentally make the playoffs next year or the year after, in which case their first-round pick goes to the Chicago Bulls, while Lillard just keeps getting older.

That was a lot to take in, so here’s the basic gist: their 2nd and 3rd most valuable players are 20 and 19, yet Lillard and their 4th best guy take up all the money on a roster that isn’t close to competing. If they make the playoffs somehow, they lose their first-round pick. Sick.

What should the Portland Trail Blazers do?

Logically, there is only one path forward, provided we all still agree winning a title is the goal: build around Henderson and Sharpe, and be a lottery team for at least the next two years. Lillard is not – and should not – be part of that plan.

It’s not obvious, per se, but professionals are running the team, so this reality should be pretty easy to grasp for them. That all begs the question of why they haven’t traded Lillard yet since this has been clear for at least the last two seasons. My explanation is something I like to call “The Ramen Shop Paradox.”

The thought experiment goes like this: logically, Lillard should have demanded a trade years ago, but he has signed extension after extension like there’s no tomorrow. Nowadays, it’s pretty clear that the Blazers should get out of the Lillard business, but they’ve reiterated their desire for him to stay over and over. The reason must be something not basketball-related like perhaps Lillard likes one specific Ramen shop in Portland and doesn’t want to leave it.

We in the biz’ call that a metaphor, since I highly doubt Lillard is making hundred-million dollar decisions based on Japanese noodle soup, but I get the sense my Offseason Strategy Consultant goals of winning a basketball championship might not actually coincide with the team’s or Lillard’s.

It’s certainly possible that Lillard just likes being the king of Portland, and at this point, he will never be the king anywhere else. A trade to Miami – the current popular fancasted trade – would slot him behind several Heat players this century in their pantheon. Perhaps he does not want to be viewed like Kevin Durant, who will always be an all-time great, but also the guy who only won a championship after joining the best team in the league.

And maybe the Blazers just like having someone to call a king. When Lillard scored 71 points last season, the whole world remembered how incredible he really is, and only Portland could call him theirs. It’s a special relationship, and that’s not something I want to undersell.

But at some point, it’s time to move on. The fans deserve a plan that can bring about a championship, and this one has a zero percent chance of cutting it. So long as we can agree that the franchise goal is to win a championship – irrespective of who is on the team – not trading Lillard approaches insanity and borders on malpractice.

The situation is more untenable for the Blazers than it is for Lillard. There’s a reason I had to assume emergency powers to try to fix it, which I will obviously be relinquishing when I feel the situation has settled. I really hope they listen.