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Damian Lillard v. Trail Blazers: The Argument for Dame

Dame’s trade request wasn’t born yesterday. Here’s why that matters.

Charlotte Hornets v Portland Trail Blazers Photo by Soobum Im/Getty Images

Damian Lillard has been the hottest topic in the NBA since he requested a trade from the Portland Trail Blazers on July 2nd, 2023. A cottage industry has grown around the crafting of trade packages for the seven-time All-Star. Close on the heels of those discussions have come debates around the seemliness of the request. Watching an impending divorce unfurl before their eyes, observers—particularly Blazers fans—are arguing root causes and who’s to blame.

At last count, the Blazer’s Edge Mailbag has received 48 distinct trade suggestions (and a host of copycats) since the news broke ten days ago. Dealing with those is near-impossible. Most are far-fetched anyway.

Lillard’s agent, Aaron Goodwin, seems intent on ensuring his client goes to the Miami Heat and nowhere else. Until that changes, we’re all along for the ride. You can press the buttons on the trade machine all day. It’s like riding one of those quarter-operated grocery store horsies: lots of motion, not going anywhere.

The other matter—assigning fault, blame, and impact—is more approachable. Today and tomorrow, we’re going to look at the issue from each side: Lillard’s and that of Trail Blazers management. We’ll use representative questions from the Mailbag as examples to seed the conversation.

For instance, there’s this...


Why aren’t you dragging Dame for requesting a trade after years of professing loyalty to the team? He signed a 60 million per year extension. He said he wants to be our greatest player ever. Doesn’t loyalty mean anything anymore? I think his reputation is going to take a real hit from this. Do you think he’s been exposed here? And why now, besides the obvious? We’ve been rebuilding for a couple years now? Why change course and go back on his word?


And this...

I’m curious about your thoughts on whether Dame and his camp bear at least some blame for the situation we’re in. Here’s what I mean: It has been at least whispered throughout the league for nearly three years that, if management couldn’t put a winning team around Dame soon, he was likely to ask out. Is there any sense that such knowledge might lead other GMs to strong arm Portland in trade negotiations with the thought there might be more pressure on Olshey and now Cronin to get something done? No one should hate Dame for asking out now, but is it at least fair to wonder how much his low key pressure on the front office (or, at least, his lack of unwavering commitment) weighed on their ability to get a fair deal?

Chris B.

And add a helping of this...

Hey Dave,

With all the reports coming out about Dame won’t report to other teams besides Miami and other stuff from his agent, I feel like it’s just painting him in such a bad light. I take it as the result of people not having much else to report on/him being such a high profile player, do you see it being something else? Could this spiral into him staying with the team going into the season? I feel if he’s still on the team at that point, he’ll be a professional and report, or is this just me being optimistic?


Let’s breathe for a second. Deep breath. You’ll feel better. Now, let’s talk.

Shifting Perspective

Although the outcome is different now, the situation hasn’t really changed from what it’s been the last few seasons. Remember what we’ve said in multiple Mailbags during that span. What happens to Damian Lillard depends almost exclusively on the choices of one person: Damian Lillard. Nothing anybody else says, thinks, feels, or claims is going to change that. We can react however we want, but that’s all we’re doing...reacting.

Lillard is in the driver’s seat. His priorities will be his own. That’s exactly as it should be. He has not just the right, but the duty, to make the best choices he can about his career, aspirations, and family. That’s part of professional life in any field.

The Trail Blazers also have a say in the process, as they are affected by it and technically carry his contract. They also have the right and duty to do the best they can for their franchise.

Both parties are going to pursue their core purpose. Likely, they’ll find a way forward that answers at least some of the needs of both, if not quite all. Lillard and General Manager Joe Cronin might need to widen their options list, at least in timing and technicalities, if not destination. To avoid a protracted battle that would be good for neither, they’ll be forced to see the situation through the eyes of the other party as well as their own. Fortunately, both have already given indications that they are willing to do so, at least after the initial posturing to indicate that each side was serious about their desires.

Here’s the thing: fans and observers are going to have to do the same thing. We’re attached as a third party to this separation struggle. In the thick of it, we too are thinking mainly of our own needs and perspectives. “I don’t want Dame to leave. Or at least I want a fantastic return if he does. If not, I want to know who to blame for it. I’d also like to know who I can blame for putting us in this situation in the first place and whether any reparation is possible.”

Notice the “I” at the center of every one of those sentences. Since we’re not Damian Lillard or Joe Cronin, we’re never going to understand, or come to a resolution with, these events through that lens. Pursuing that path, we’ll lose contact with the parties involved, objectifying them as scenery in our own drama...ironically the exact thing we want to fault the principals for doing to each other.

If we want to get a handle on this, we need to step back, viewing the situation in context. History matters. Experiences matter. The people involved matter. Basic, human realities and the mechanisms of human-derived systems matter too. All of these things factor into this moment and the decisions that come from it.

Important Caveats

Getting in the mind of other people is tricky even in theory, impossible in reality. The best we can do is paint the situation as clearly as we can, then imagine standing in the other guy’s sneakers.

Not only am I not Joe Cronin or Damian Lillard, I do not have any inside information or a direct line to either party. I haven’t even come close to discussing this with either. That’s Chris Haynes territory, not mine.

Either principal might read a post like this and say, “These factors don’t matter to me.” That’s perfectly appropriate. We’re not claiming to read the minds of particular people here. We’re just discussing situations.

Diverging Realities

Damian Lillard did not wake up on July 2nd with the sudden realization that he wanted a trade. The decision point was a long time coming. Many will point to Portland’s recent performances as a contributing factor, but the roots go deeper than that.

During his 11-year NBA career, Lillard has experienced multiple inflection points. A couple stand out prominently now.

In 2015, Lillard watched as All-Star teammate LaMarcus Aldridge left for the San Antonio Spurs in free agency. At the time, Lillard indicated that he had pitched Aldridge on staying. The franchise stalwart left anyway.

Some would draw parallels between the stars, but those are thin, at best, Lillard and Aldridge are different people. Aldridge’s situation in 2015 is different than Lillard’s is now. Their approach to the team, and to loyalty, has been different. It’s unlikely Aldridge’s departure gave Lillard any direct inspiration in this moment, other than foreknowledge of the difficulty inherent in these transitions.

Instead, let’s look at what happened right after Aldridge left.

In 2015-16, without Aldridge, the Blazers were predicted to win between 25-33 games. They won 44, advancing to the second round of the 2016 NBA Playoffs after defeating an injury-riddled Los Angeles Clippers team in the first.

The team’s reaction after that season was self-congratulatory. Both Lillard and then-lead-executive Neil Olshey crowed about the disrespect heaped on the franchise and how the team had prospered, proving everyone wrong. Note that 44 victories, a 5th-place finish in the conference, and a 4-2 win over a team that lost Blake Griffin and Chris Paul during the series was described as near-overwhelming success.

In context, the claim was valid. The team had exceeded expectations wildly. This provided lift, juice for the era to come, which now featured Lillard and backcourt mate CJ McCollum as cornerstones. The 2015-16 performance erased the memory of the “unfaithful” Aldridge and set the blueprint for the future.

Lillard himself was comparatively young at the time. Unabashed celebration was not only warranted, it was natural. No context was available but the present. And in the present, he had taken the helm of the team, which had crushed it. Bravo.

From that moment onward, though, overselling success would become a staple of the franchise. Everything the Blazers accomplished was described in superlative terms. Each bit of evidence—crafty summer deal or advancing to the 2019 Western Conference Finals—served to bolster a conclusion already made: Portland was successful and right, by definition.

Though Lillard started at the same point in 2016, his journey would begin to diverge from the team’s in the coming years.

As his career grew, Lillard experienced unbridled personal success. All-Star and All-NBA nods put him in the company of the league’s elite players, who were succeeding in absolute terms, not just relative.

Lillard also became well-known among national media and experts. As time passed, they would point out the distance between Lillard’s incandescent talent and the much more muted achievements of the Trail Blazers...a reality that the franchise itself refused to acknowledge.

Finally, Lillard encountered a reality universal to athletes: age spares nobody. General Managers and Coaches can serve until they’re senior citizens, planning strategy for decades. NBA players are on the clock from moment one, a reality that becomes all too apparent as the Big 3-0 approaches.

Over the course of the eight years after Aldridge’s departure, Lillard’s reality and the team’s began to separate. Moment by moment it was indistinguishable. Lillard remained what he claimed to be: a leader for the Trail Blazers, franchise face and cheerleader. His demeanor and approach seldom wavered, at least not until the very end. But the lengths he had to go to in order sell the story increased as time passed.

At least outwardly, the team remained oblivious. Or worse, complicit. Lillard became their chosen veneer, a public-relations panacea. Disappointing record? That’s OK, we have Dame. Mediocre forward signings? No problem. Dame doesn’t need that much. Need to sell more tickets? Here’s the latest Damian Lillard highlight package, his list of accolades, and his State Farm commercial. He’s on YouTube shooting halfcourt shots with LeBron James and on TV with Chris Paul. Portland must be big time!

In reality, the team wasn’t getting better. Once they got past 2019, they got steadily worse. No matter how hard they tried, they couldn’t remedy that situation.

It’s unlikely that Lillard was looking for miracles. He knew as well as any NBA observer that the Magic Trade to turn the Trail Blazers into instant champions was non-existent. But a change in direction wasn’t too much to ask move or thread to provide a link between the team’s reality and his, providing promise that the two could be reunited.

It wasn’t forthcoming.

Selling Dame

The Blazers certainly tried. They made several moves over several years, trying to find the combination of players to right the course. Lillard not only had a front-row seat to the changes, he was—in some ways—the audience and main target.

We’re used to viewing Portland’s modus operandi from a fan’s point of view. Without presuming that we understand or speak for Lillard himself, let’s empathize for a minute what the progression might have looked like from the inside.


Portland’s rotating carousel of forwards between 2015-2023 has been near-legendary. Moe Harkless and Al-Farouq Aminu gave way to Trevor Ariza, Rodney Hood, and, Carmelo Anthony, who themselves made way for Robert Covington and Norman Powell, followed by Larry Nance, Jr. and Josh Hart. All of these players preceded Jerami Grant, who proved the pinnacle of the crop. But the Blazers haven’t won yet with him either.

By all accounts, Lillard welcomed all of these players. He is well-known for embracing teammates, by they famous or temporary. I don’t believe for a minute Lillard objected to or regretted any of these moves, nor the ones we’re about to mention.

That doesn’t change the fact that Lillard hasn’t experienced one or two, but five reboots in the starting forward positions since he took over unquestioned leadership of the team in 2015. Whatever plan the front office tried to sell him on this summer would be the sixth. If you count Aldridge leaving, the seventh.


Portland’s shooting guard position has paralleled that trend, though not as strongly. CJ McCollum was Lillard’s long-time companion in one of the best backcourts in the NBA. No matter how many points they produced, they couldn’t outduel Steph Curry and Klay Thompson. When the Blazers traded McCollum in 2022, most considered it long overdue.

McCollum was followed by Simons. Though his trial was incomplete, current evidence suggests that a Lillard-Simons pairing won’t exceed the effectiveness of Lillard and McCollum.

Now, in 2023, the Blazers selected one of the darlings of the 2023 NBA Draft, Scoot Henderson. The rookie’s talent is unquestionable. His fit alongside Lillard would be. And even if it weren’t, this would now be the third sales job the front office would have to make, convincing Dame that they had finally found the backcourt teammate he’s been waiting for.

Definitions of Success

In 2021-22, Lillard had abdominal surgery. The team tanking during his absence was more than understandable. They nabbed the seventh overall pick in the 2022 NBA Draft, choosing Shaedon Sharpe, a hyper-athletic guard with a high ceiling who will probably take 3-4 years to develop fully. Fair enough.

Lillard returned big-time in 2022-23, to the tune of 32 points per game, the best statistical season of his career. During the summer of 2022, he made public statements saying that not only was he ready to play again, the team was now ready to advance. In no way would they be repeating last year’s tanking experience.

By the time Lillard made his seventh All-Star appearance, it was evident that the lottery was a likely outcome of Portland’s season yet again. They sat him, defining success by ping-pong ball odds. Bonus: that’s how they got Henderson. Sadness: that might have been how they lost Dame.

Leaning on Loyalty

Viewing these events in aggregate, the old adage seems apt: fool me once, shame on you. Fool me five times and three more times and two times in eight years...

The question remains: Was winning in the mid-40’s a worthy goal? Ducking the luxury tax? Accumulating future assets? At least publicly, the franchise seemed content with these shifting priorities. They had to be, as they had little practical alternative. And they could be, because they always had Dame. As long as he was willing to redefine success in the same way, that is.

There’s at least some evidence that the organization felt that Lillard’s loyalty would perpetuate regardless. To this day, Cronin affirms that their intent and desire was (and is) to build around Lillard. Blazers staffers—publicly and privately—have dragged this author and this website for even suggesting that a Dame deal, or Lillard asking out, was a possibility.

No matter what the organization thought—or convinced itself of, or was convinced of by Lillard’s public proclamations—it seems pretty clear that their definitions/aims and his had been diverging for a long while.

That reality was couched in Lillard’s language when he affirmed his desire to stay with the team. His phrasing morphed from variations of, “Trail Blazers always!” to, “I’d like to bring a championship here if I could...” to, “The team has made me promises. Now we’ll wait and see.”

Understandable Change

That shift in language is pretty easy to understand, given the circumstances.

Imagine being told again and again that the real solution had arrived, only to find that it hadn’t. How is one to view the Next Big Guard and the Next Complementary Forward after so many repetitions of the same refrain?

Imagine also the cognitive dissonance of hearing, “We’re building towards a contender,” while watching your team acquire only young players, trade away veterans to save salary, and draft a prominent rookie whose natural position duplicates your own.

Imagine the feeling of playing the best basketball of your career, knowing that the chances to do are limited, and having that amount to a season capped by lineup doctoring to engineer lottery odds.

By the time that season ended, it appeared Lillard was as willing to listen to Portland’s next promise as ever. The difference was, this time he would demand results. When those weren’t forthcoming, it was time to acknowledge the relationship change that had been progressing apace for several seasons.

Evolving Perspective

Understanding all of this, we can come to a couple of conclusions about the current situation, even if we don’t comprehend it perfectly.

Even though Portland’s moves (or non-moves) over the last few weeks were a catalyst for Lillard’s trade request, they were not, in themselves, the cause. Those roots go far deeper, and have been present far longer. No single decision, or person, bears the blame. In fact it’s possible that, as with many end-stage separations, nothing outside of a universe-changing miracle could have avoided the break-up. Just taking out the garbage and returning to normal isn’t going to repair a marriage with deep, unacknowledged divisions.

The Trail Blazers and Lillard both bear responsibility for the split. Fixing it would require a time machine, going back and convincing them to do something different by giving them foreknowledge nobody could have. Such fictions are tempting to believe in during times of trauma, but they’re hardly helpful.

We must also acknowledge that interpretation of these events falls on a spectrum. On one end lies the fan/organizational lament, “Why did you have to ask for a trade?” The other end reads, “You should feel lucky I waited so long.” Having read the above, you’ll understand the justification for that second view.

Lillard could have rightfully asked out two seasons ago, or four. He’s paid to play basketball under the NBA umbrella. He’s not paid to bridge the gap between his organization’s claims and reality, let alone to throw himself in them. That he did so, for so long and with such public grace, is more than can be reasonably expected.

Reading tea leaves and picking up on quiet buzz, my impression is that only when it became evident that this role would not change—at least the way we’ve defined it above, that tangible team success would not replace relative, and that he’d have to spend the rest of his career in Portland making up the difference—did Lillard finally acquiesce and request a trade.

Further Consequences

Two burrs remain in the saddle, if questions and claims in the Mailbag are any indication.

The first is whether Lillard should have signed his contract extension, given the circumstances.

Keep in mind that not only were those circumstances different at the time of the signing, the Blazers were doing what they had always done—what they continue to do even after his trade request: profess a desire to keep Dame and build around him.

Though the divergence of star and franchise seems obvious in retrospect, it was probably not so living through it in real time. Perhaps Lillard believed, as his General Manager did, that real change was not just a possibility, but on the horizon. Perhaps, at that moment, bring the face of the franchise and making everything seem good wasn’t an undesirable role for Dame...or the $60 million a year extension seemed like a fair price for the job. Having taken less than the max earlier in his career would only strengthen the justification for getting it now.

Either way, the assertion made at the beginning of this piece held then as it holds now. Damian Lillard is responsible for doing the best, smartest thing for Damian Lillard. Signing that extension was definitely that. It was absolutely proper for him to do so.

The powers that be in the NBA might look at cases like this and advocate for a rules change. Nobody likes the idea of a star signing for max money, then demanding a trade at all, let alone shortly after. But this is the same as divorce lawyers and judges advocating for a change in overarching laws. It has nothing to do with your particular divorce in the moment, nor will it affect it in the slightest. They’re not making those changes because they don’t want you to get screwed. They’re making them because they don’t want to get screwed if they end up in that situation.

In that way, the point is moot. The Blazers offered the contract. Lillard signed it. It’s official. End of story.

The second is whether Lillard’s reputation will be affected by this in any way.

Every player will take a public relations hit for demanding a trade. Lillard’s will be as small as anyone’s could be. He’s traveling in the wake of Kevin Durant and enough other predecessors to make this a common occurrence. Most NBA pundits were suggesting he be traded 1-2 years ago. They’ll view this as justification of their stance rather than an indictment of his character. If anything, they’ll praise him for staying as long as he did.

If any jagged edges show, Lillard’s agent will do his best to absorb them, protecting his player. That’s what he’s there for.

The final national verdict on this matter will be, “Portland couldn’t build a contender around Lillard.” Any other narratives that come up will be squashed the first time he scores 30 for the Heat. Miami will then be “where he’s supposed to be”.

Feelings will run hotter in Portland, of course. Time will soothe those too. The first time Lillard returns to the Moda Center in an opposing team’s uniform he’ll get an extended standing ovation. He’ll be applauded every time thereafter. When he retires, the Letter O will hang in the arena rafters. There’s a good chance he’ll become a spokesperson for the team or, if he desires, part of its executive core. The franchise will be willing to use him in his middle years the same way they used him when he was make everything seem better.

If certain issues get swept under the rug in the process, well, that’s been going on for a long time now. The joy of remembering the greatness of Damian Lillard will far exceed any quibbles about the transition period surrounding his trade request.

The only way that narrative changes is if both sides play hardball and the season starts with Lillard sitting out because the Blazers haven’t traded him. The franchise will do everything they can to make sure that doesn’t happen. Should that juncture arrive, Dame himself might opt to play, as Durant did with the Brooklyn Nets last year, to avoid the awkwardness. Turning this ugly benefits neither party.

In the end, the years Lillard will be remembered as one of the top players in franchise history will far outstrip any months he spends in limbo this summer and fall. That is as it should be.

From his perspective, and in the view of many others, Damian Lillard has done nothing wrong in this process, neither playing nor staying nor asking out. He’s done more than most would have, being put in a less-than-ideal position. Those who don’t agree can perhaps see his point from where they stand, at least.

Can the same be said of Joe Cronin, though? Tune in tomorrow.