On the Optics of Damian Lillard's Trade Request and the NBA's Warning Memo
Lillard's trade request may be coming too late in the game to land the way he and his representatives hoped.
In the full month since Damian Lillard requested that the Trail Blazers trade him to the Miami Heat, there has been a lot of talk and not much action. A lot of leaks and not much traction on an actual deal, either with the Heat or anyone else. A lot of posturing and not much give from either side. That's the way it's going to stay, until it doesn't.
The memo the NBA league office sent to all 30 teams on Friday about Lillard's request for the Blazers to trade him only to Miami probably isn't going to change much. But it does crystallize why the whole thing is taking as long as it is to play out, and why Lillard might be pushing for this move two years too late to get the public support he and his representatives thought they would.
In recent years, whenever a star of Lillard's stature has requested a trade, the default position of the public has been to take the side of the player. This has been especially true in the case of Lillard, who has seen a multi-year campaign from certain debate-show personalities, practically begging him to do what they felt was best for his career.
So now that Lillard's trade request has been here for a month, why isn't it landing the way he and his representatives hoped?
Everyone understands why Lillard wants out of Portland: Blazers general manager Joe Cronin tried and, by his own admission, "failed" to build the kind of supporting cast Lillard wanted, and drafted his successor in Scoot Henderson with the No. 3 overall pick in June. The validity of his trade request is not a question in anyone's mind. Even Cronin said he gets where Lillard is coming from.
But when Lillard finally reached the breaking point and asked out, it happened late enough in the "player empowerment" era that, even though most of the NBA world had wanted him to do it for several years, the story felt played-out. There have been one or two of these just about every summer since The Decision in 2010, and there has been a slow creep of them happening with more and more years left on the player's contract.
In 2023, a superstar requesting a trade or changing teams is no longer a league-shaking event. It's an expected part of the NBA transaction cycle, accompanied by an interminable cycle of leaks, counter-leaks and Trade Machine proposals from fans on Twitter. It doesn't hit the same anymore. James Harden is on his third one of these in less than three years and it barely registers now. Star movement these days feels more like playing Mad Libs with recognizable names than roster building that makes sense. Chris Paul is on the Warriors now? Sure!
Lillard and his agent, Aaron Goodwin, weren't given this slap on the wrist by the league for requesting a trade, or even for stating a preference for a specific team. They were given the warning for the same reason the Heat, Sixers, Knicks and Bulls have been hit with tampering punishments in recent years ahead of free agency even though everyone does it—they were too sloppy and too public about it.
The zero-to-100 nature of their messaging didn't do them any favors, either. Goodwin insinuating in multiple on-the-record interviews that Lillard would hold out if he wasn't traded or was sent anywhere besides Miami was a threat people in the league took about as seriously as they took LeBron James pretending he was considering retirement a couple of months ago. The rhetoric was so starkly in contrast to how Lillard has conducted his entire career and the "loyalty" brand he's built that it was wholly unbelievable. I still think there's approximately a zero percent chance he won't show up and do his job if he doesn't start training camp as a member of the Miami Heat.
Lillard's camp, through various leaks, has trial-ballooned various talking points designed to get the public on their side and pressure the Blazers into sending him to Miami. None of them have really worked.
They tried "free agents won't want to go to Portland if they don't do right by Dame," and that didn't take—as if Portland ever got free agents in the first place.
They tried "Portland's young players are watching how they treat the franchise's all-time leading scorer on the way out," and that didn't take, either—as if Henderson will be upset by getting to play with one of his idols, or his team getting better players back for Lillard than what the Heat have.
Cronin, for his part, is in the position to have to clean all of this up because he was unable to deliver on his own too-public promises to build the kind of contender Lillard wanted. That's why nobody with any sense begrudges Lillard the trade request, and why no Blazers fans that I've talked to in the real world (ignoring Twitter bots) wish him anything but the best when he is eventually playing elsewhere.
But the idea that, because Cronin didn't deliver on his pledge to build around Lillard, he now has a duty to gift-wrap him to Miami is another talking point Lillard's camp thought there would be much more of a public appetite for than there actually was. In reality, if Cronin valued the third pick too highly to trade it for a sub-superstar veteran, not too many people believe he wouldn't value Lillard just as highly. Or at least, a lot higher than the limited trade assets Miami has.
Since Lillard's trade request, you've started to see small-market executives close rank behind Cronin. New Orleans Pelicans GM David Griffin discussed the situation in a radio interview earlier this month and compared it to his own handling of Anthony Davis' trade request in 2019.
In the weeks leading up to the draft, front-office members from several other small-market teams advised Cronin against trading the third pick because of how hard it is for non-destination franchises to get that kind of talent in the door. I wouldn't be surprised at all if Cronin is hearing similar pleas right now from his peers not to let himself be pushed to send Lillard to Miami for a subpar package with four years remaining on his contract.
Cronin has said his goal in any Lillard trade is to make the best deal for the Portland Trail Blazers, but I wonder if he's also feeling pressure not to be the GM who sets the precedent that star players with this many years left on their contracts can force their way where they want regardless of what comes back in the deal.
The NBA is clearly worried that things have gone too far down that path, or at least worried enough to send out that memo, even if it was mostly performative and may not ultimately prevent Lillard from ending up in Miami. He isn't the first star to want a trade, or even the first one to want a trade to a specific team, and he won't be the last. If the league hadn't said something about this one, it would have been the next one that got the formal warning. Lillard's trade request and Miami-only edict just happened to be the one that pushed it over the edge.
If Lillard had pushed his way out of Portland in the summer of 2021, after the Blazers lost in the first round to a shorthanded Denver team, he may have gotten where he wanted to go faster, with just as much public sympathy as he has now, if not more.
At the time, Lillard was in the midst of a power struggle with then-general manager Neil Olshey, in part over Olshey's reluctance to give him a two-year, $122 million contract extension once he became eligible for it. Olshey was fired that winter after an investigation determined he'd violated the team's code of conduct, and then Lillard signed that extension—his second with the Blazers in addition to the rookie max that everybody signs—last year.
A viable trade offer from Miami hasn't emerged, but no one else has entered the bidding in a real way, either. Lillard may still get his way in the end. The NBA is trying to put the genie back in the bottle with the Friday memo. It's probably too late in the game for that. But it's also too late in the game for Lillard to do this and be celebrated for it the way he would have been two years ago.