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Instant Reflections on Damian Lillard’s Trade Request

The good, bad, and ugly of the Trail Blazers soap opera.

NBA: Portland Trail Blazers at Utah Jazz Rob Gray-USA TODAY Sports

Damian Lillard has finally requested a trade from the Portland Trail Blazers. It’s a watershed moment in franchise history. The last such juncture came in 2015, when All-Star forward LaMarcus Aldridge chose between the Blazers and San Antonio Spurs in free agency, leaving Portland for Gregg Popovich and the lure of NBA titles. Before that, medical reports foreshadowed premature career endings for Brandon Roy and Greg Oden. Lillard’s request stands with those three events as the most significant inflection points in Portland since the turn of the millennium.

We’re going to cover the implications of the Big Moment in this post. Two things we won’t do here. This will not be eulogy for Lillard’s career or his time with the Blazers. We’ll save that for when he’s actually traded. Neither will we lead Portland in a chorus of Achy-Breaky Heart. Feel free to mourn and reflect about the interpersonal/emotional implications in the comment sections of our various articles today. We may get there too, officially, but not right now.

Instead, let’s look at what this means for the Blazers themselves, the things they’ll be dealing with over the next few weeks.

New Direction

First, and most obviously, the franchise will head in a new direction after this move. For eleven seasons, Lillard has been the panacea in Portland. Bad game? Dame scores 30. Bad season? He made the All-Star and All-NBA teams. Playoffs ouster? Did you see that amazing last-second shot??? Lillard’s talent and charisma have shaped the franchise with unmistakable gravity, to the point where their identities merged indistinguishably.

Whether that was healthy or not is debatable. Either way, Portland won’t have that relationship to lean on anymore. They’re going to have to stand or fall on their own merits.

They’re also going to need to engage in a true restructuring. Veterans Jusuf Nurkic and Jerami Grant are likely on their way out over the next year. Anfernee Simons suddenly has new life and carte blanche to develop fully. Shaedon Sharpe and Scoot Henderson aren’t the backcourt of the future anymore. Their contributions will be immediate. They’ll take their knocks and grow their careers starting now, today.

“New Direction” may be a bit of a misnomer, though. Realistically, the Blazers have been pointing in this direction since General Manager Joe Cronin took over for Neil Olshey. Over the past two years, they’ve restructured their salary ledger, brought in young players, and angled for draft picks rather than importing proven-but-expensive veterans. This is exactly why Lillard, reading the same wall-writing as the rest of us, finally pulled the plug.

If the Cronin regime is to be critiqued, it’d be on the failure to execute a star trade beyond Grant. The criticism would be predicated on stars being available, though. With the Toronto Raptors and Brooklyn Nets white-knuckling OG Anunoby and Mikal Bridges like their lives depended on it, there’s no indication such a trade was possible. Kevin Durant was unreachable. Bradley Beal was the wrong player. Few other usable stars have moved between Cronin’s start and now.

Given those circumstances, Cronin wobbling the line between Lillard-based hope and rebuild reality has been understandable. It’s half-miraculous that both sides were able to keep up the relationship as long as they did.


The entire fan base will have to adjust when Lillard is moved, for all the reasons mentioned above and more. But let’s be clear what we’re mourning.

Blazers fans are going to miss 2019 Damian Lillard something fierce. Videos of The Shot—and plenty of other moments—will live forever on YouTube. A generation of Portland fans will tell their grandchildren about them...grandchildren who will then roll their eyes because the video isn’t displayed in seven dimensions.

Blazers fans will not miss the reality of the past two seasons, with Lillard recovering and sitting out so his team could gain better lottery position, a tug-o-war playing out in the media, and supporters (often including team representatives themselves) sniping at everyone around them that even mentioning a Lillard trade was blasphemy.

In that way, a new direction is needed. Paradoxically, resetting expectations around a Sharpe-Henderson backcourt may unite the team and fan base where Lillard’s yo-yo saga had divided. The product might be worse for a while (although 33 wins sets a low bar) but the process might be better.

Potential Trades

The Blazers community will talk about potential trades until a deal actually gets executed. For now, let’s set parameters.

  • Bringing back veterans will not help Portland at this point. They’re not going to contend in the next three years. And they don’t need any more guards, thank you.
  • Bringing back young players might be of value, but they’re already well-stocked with players under 25. They would like a young star-in-waiting, but they don’t need youth for its own sake.
  • The Blazers are well-positioned to take on bad contracts as long as they don’t run more than 2-3 years. As long as they don’t exceed the luxury tax, it won’t hurt them.
  • Future capital has out-sized value to the franchise right now.

Given these realities, the names Portland gets back in a Lillard deal probably won’t matter. Unless they can pry Nic Claxton from Brooklyn or Anunoby from Toronto, they’ll probably acquire players whose contracts they can run out or players they can turn around and trade again in 6-12 months.

Premium draft picks, on the other hand, are worth their weight in gold. That paints a huge target on the Nets as trade partners. The Heat might get there, though they can only offer picks from 2028 or later.

Wherever they get them, obtaining unrestricted future picks that have a good chance to fall in the lottery is Portland’s best path onward. That would allow them to layer their rebuild, bringing in a new crop of high-value rookies just as their current crop is entering their early prime.

Ongoing Issues

Besides the obvious problem of trade partners, the Blazers have a couple of immediate hurdles to negotiate.

The first is Grant’s status. He and the Blazers agreed to a five-year, $160 million deal on the opening night of NBA Free Agency, 2023. Lillard’s announcement came less than 24 hours afterwards.

Odds are, Lillard’s move did not change the calculus of that offer. Portland had serious incentive to retain the 29-year-old forward. They no doubt planned to the moment they traded for him in the Summer of 2022, knowing he would enter free agency this year. They gain zero salary cap space, and would lose a trade asset, by letting him go.

It might have been to Portland’s advantage to know which way Lillard was leaning much earlier in the process. Dame holding on so long is seen as a sign of loyalty to the club, but it also inhibited their ability to plan. That’s water under the bridge at this point.

Grant’s place with the team will change with Lillard’s departure. As one of the league’s best complementary players, bereft of veterans to complement, he will be a candidate for trade, beginning in Year One. Reconciling that reality while supporting a growing team will be one of the interesting stories of the season.

Ditto that for center Jusuf Nurkic, also under a multi-year deal and no longer as critical to Portland’s future as he was with Lillard on board.

Portland’s second issue is one of Public Relations. Popular reaction to Lillard outside of Portland will be near-unanimous: “It’s about time!” Dame will be seen as smart and properly self-regarding for seeking to join a contender.

The Trail Blazers’ reputation will take more of a hit. Their participation in this story will be summed up as, “Couldn’t build a contender.” Though that’s been self-evident for 20 years or so now, Lillard’s departure will put a huge imprint in the cement.

Portland must now begin to turn around that narrative, keeping the concrete wet enough to smooth it over. If they don’t begin to counter that description with some kind of tangible success in the next generation, they risk being recast as a non-serious team that exists simply to overpay second-tier players on their way to other destinations or out of the league entirely.

Lillard leaving puts a bow on any residual mystique the franchise claimed to have from past eras. They’re too far back now, buried under continual bad timing and occasional mismanagement.

The Blazers can’t retain Lillard, but they can’t spend too long mourning him either. They need to generate forward momentum, building a contender over the next decade. Even if they aren’t able to justify themselves in this extended Dance with Dame, winning in the future would retroactively prove these events sound and justifiable. Any other agenda—and we’ve heard plenty over the past 10 years—will simply be decoration on a slowly-rotting cake. Portland can’t afford that any longer.

Over the next few weeks, it’s time to say goodbye to Dame. Then it’s time to win without him. Portland needs to do both well, lest the franchise become what people say it is rather than what it needs to be.