Damian Lillard Requests a Trade from Trail Blazers: How They Got Here and Where They Go

Lillard wants to be in Miami. The Blazers want to make the best deal they can. Where does it land?

When Damian Lillard and his agent, Aaron Goodwin, met Monday with Trail Blazers general manager Joe Cronin to discuss the direction of the franchise, many assumed the end result would be a trade request.

It didn't come that day, and for a short time, it seemed it never would. At the very least, Lillard would give Cronin one more chance to make meaningful improvements to the roster in the first 24 hours of free agency to make it up to him for the decision to take another point guard, Scoot Henderson, with the No. 3 overall pick in last week's draft.

Those additions did not happen, and the decision to hold off earlier in the week turned out to be only a delaying of the inevitable.

Word of Lillard's trade request came down Saturday morning, with Turner Sports' Chris Haynes first breaking the news as expected.

Quickly, focus turned to Miami and Brooklyn, the two teams Lillard has long been rumored to hold as his preferred landing spots. Other teams—the Sixers, Clippers, Knicks, Jazz and Spurs—have come up as hypotheticals, but it's now understood that Miami is where Lillard wants to be.

Usually, stars on his level get what they want, and get where they want. Maybe that will happen again this time. Right now, the Blazers are at least putting up the appearance that they'll be fielding other offers.

"We have been clear that we want Dame here but he notified us today he wants out and he’d prefer to play someplace else," Cronin said in a statement on Saturday afternoon. "What has not changed for us is that we’re committed to winning, and we are going to do what’s best for the team in pursuit of that goal."

Lillard will almost certainly be elsewhere when training camp opens in September. The deal could happen tomorrow, or it could drag out into August as these things tend to do when the team with the disgruntled superstar doesn't get an offer they like.

There will be plenty of time this summer to unpack Lillard's 11 unforgettable years in Portland, everything he's meant to the organization, city and fanbase. But the reality at hand must be dealt with first.

How Lillard and the Blazers got here is nuanced and multi-layered, as any breakup of a marriage that's lasted this long will be. Where things end up is equally tricky.

When Cronin took over as interim general manager in December of 2021, following the investigation and eventual firing of longtime president of basketball operations Neil Olshey for violating the team's code of conduct, he inherited a flawed and expensive roster that had run its course, having had consistent playoff success but never a true contender. He also inherited Lillard, the most low-maintenance, easy-to-work-with superstar this side of Tim Duncan, someone who just gets every part of how to be a franchise player in a small market on and off the court.

Lillard had by this time built up a reputation as the rare superstar that did things "the right way" and wasn't itching to leave for a bigger market and chase a superstar team-up. But even he had grown restless just a few months before the front-office change. Following Portland's 2021 first-round playoff loss to a Denver team missing Jamal Murray and Michael Porter Jr., Lillard said publicly multiple times that he needed to see more "urgency" in building a contender. Olshey responded by firing head coach Terry Stotts, insisting the playoff exit was "not a product of the roster," and attempting to pin the controversial hiring of his hand-picked successor, Chauncey Billups, on Lillard to deflect backlash over a 1997 sexual assault allegation against Billups.

That was the same summer Lillard watched Giannis Antetokounmpo, another small-market superstar lauded for his commitment to doing it "his way," win a title in Milwaukee after the Bucks traded multiple first-round picks for Jrue Holiday to upgrade a roster that had maxed out below contender status. Lillard wondered where that all-in push was from the Blazers, and if it would ever come. Olshey was too attached to C.J. McCollum to ever be willing to make a serious offer for one of those players on the trade market, and was all too happy to point out as often as he could that free agents didn't want to come to Portland.

It was hard to blame Lillard at the time for wanting more in return for everything he'd given the franchise. And Olshey's ouster and the elevation of Cronin, a Blazers lifer and well-liked scout and cap expert who had survived several front-office regime changes dating back to 2006, offered a chance at a fresh approach.

From the time he took over, Cronin was upfront that it would take time to get the roster to where he felt it needed to be. He said it would take multiple cycles of transactions—drafts, trade deadlines, free-agency periods—to clean up the cap sheet and recoup some of the draft assets Olshey had given up in shortsighted deals in years past. There was essentially an understanding—between Cronin and the public, and more importantly, between Cronin and Lillard—that it would be an 18-month runway before it was time to push everything in and go full-bore towards a title run. The extension Lillard signed last summer, which will pay him $216 million through 2027, was a show of faith in Cronin to follow through.

That part, for reasons both in and out of his control, is what Cronin has been unable to deliver, which is why the trade request finally came on Saturday. A few key decisions—drafting Shaedon Sharpe last year rather than trading the No. 7 overall pick plus other assets for O.G. Anunoby, taking a step back at this year's trade deadline and, most recently, taking Henderson with the third pick in the draft—have led those in Lillard's camp to wonder well before this week whether the new front office was already looking towards life after him.

Over the past six months, at every turn, Cronin's words have said one thing and his actions have said another.

After a trade deadline in which he traded away Josh Hart and Gary Payton II for young players and draft assets, Cronin said that he was "borderline-anxious" to make an all-in championship contending push.

"We're going to be ridiculously aggressive, to the point where once we push our chips all the way in, you might look and say, 'Wow, they lost that deal, they gave up a lot for that guy,'" Cronin said at the time. "But that's just us pushing our chips in. We feel extremely obligated to put a great roster around Damian Lillard. And when I say we, that's from the top. Jody [Allen] and I have had a lot of conversations about how important it is for us to do right by Damian, and we plan to do that."

Cronin doubled down on that stance in April at his end-of-season press conference, following an embarrassing 56-point blowout loss to Golden State capping off a 2-15 finish to the season.

"I think moving forward, we're not going to be in 'Let's try to find a player' mode," he said then. "We're going to be more in win-now mode, where the rotation is going to be much more veteran-laden than it was this year."

Even following Thursday’s draft, after Cronin elected not to trade the No. 3 overall pick and instead used it to draft someone who played the same position as the franchise cornerstone he was supposed to be building around, he insisted that the plan hadn't changed.

"It is," Cronin said when I asked him directly on draft night whether or not the plan was still to put a contender around Lillard. "There's nothing we want more than, number one, for Dame to retire a Trail Blazer and two, to put together a high-end winner. I think that's what gets misconstrued about Dame sometimes. For us, it's an incredible problem to have. We have the best player in Trail Blazers history, who wants to be here and have a winner put around him, and that's our challenge."

During the same time that Cronin was publicly making promises he either couldn't or didn't want to follow through on, Lillard was not exactly helping the cause, either.

His much-publicized remark at his own April exit interview that he didn't want to play with more 19-year-olds was essentially an ultimatum to Cronin to trade their lottery pick or lose him, even once the pick moved high enough in the lottery that there was no way to trade it without clearly losing the deal.

(For what it's worth, I've been told Lillard's "no more 19-year-olds" stance would not have applied to Victor Wembanyama. If Portland had won the draft lottery, we wouldn't be having this conversation right now.)

During the first round of the playoffs, Lillard appeared on an ESPN game broadcast with Stephen A. Smith—who has been openly begging him to request a trade every day on national TV for several years now—and said he'd "have a decision to make" if the Blazers didn't pull off a big trade.

Things really picked up in early June when Lillard appeared on the Showtime boxing show The Last Stand and talked openly about wanting to play with Mikal Bridges in Brooklyn and Bam Adebayo in Miami. That interview blew up so much that Lillard had to walk it back on Instagram Live a day later. The infamous Instagram video of the Will Smith song "Miami" playing in a club during Lillard’s vacation to Paris got enough attention that Goodwin felt compelled to issue a statement denying that it was intentional.

Lillard could have shut all of this down if he wanted to. It's not hard to say no to some of these interview requests for shows where you know you're going to be led into speculating about your future. Over the past several years, I've rolled my eyes every time a national writer has parachuted into Portland to profile Lillard and told me their angle was going to be "loyalty." It's been done to death, and I know Lillard and his camp feel the same way, yet they kept taking the requests. Part of it is that Lillard is, truly, too nice of a guy to say no to this stuff, and another part is that he's always been honest to a fault. It's what makes him as great a leader as he is, but it isn't exactly convenient when the Blazers are trying to preserve leverage, for him to be openly flirting with other teams by name in interviews.

Between Cronin telegraphing the Blazers' intentions as strongly as possible since the deadline and Lillard walking up to the line of requesting a trade in every interview he gave since the season ended, what chance did they have of getting anything done? Why would Brooklyn entertain conversations around Bridges, even for the No. 3 pick, when there was a sliver of a chance they could get Lillard if things went sideways? Why would any team with one of the impact veterans Cronin was looking to add not ask for the world, knowing he had to say yes or risk losing the franchise's all-time leading scorer?

I don't believe, as a loud subsection of the fanbase does, that Cronin was ever lying about wanting to keep Lillard around. I don't think he was secretly trying to push Lillard to leave, or that Blazers ownership is happy about shipping out the most reliable ticket- and jersey-seller in recent franchise history.

I think Cronin naively thought, because he had a more open and transparent working relationship with Lillard than Olshey ever did, that Lillard would continue to trust his long-term vision. That Henderson and Sharpe were so special that Lillard would soften his stance on a youth movement and give him yet more time to find the exact perfect "swing" to take.

In the end, Cronin chose not to make a deal he might lose, and as a result is going to lose the superstar those deals would have been building around.

How Cronin handles the coming weeks—maybe months, depending on how long it takes—will determine whether he'll be more successful building after Lillard than he was building around him.

Already, the public negotiations are starting. Lillard and those close to him are adamant that it's Miami and only Miami. The Blazers have been signaling to other teams that they're looking for the kind of package of picks and prospects that a player of this stature usually fetches on the market.

The Heat's potential offer is self-evidently unworkable on any grounds other than getting Lillard where he wants to go: Tyler Herro, going into the first year of a four-year, $120 million extension, playing the same position and role as Anfernee Simons for more money, plus first-round picks five and seven years out, from a franchise that has missed the playoffs four times in the past 20 years. Word is already circulating that Herro would have to be re-routed to a third team for the Blazers to consider it; if there was a market for attractive draft assets and young players for Herro, that's a deal Miami would have already made in preparation for these talks.

The Blazers are under no obligation to send Lillard to Miami if they can't find a way to improve their offer. He doesn't have a no-trade clause like Bradley Beal did, although the size of his contract will scare some teams off if they aren't certain he'd be open to playing there.

Since the lottery, despite what he's said publicly, Cronin has put the best interests of the franchise ahead of the best interests of the franchise player. It's not a bad strategy for a relatively unproven executive wanting to show he won't be pushed around. Acquiescing now to Lillard's wishes and sending him to Miami for pennies on the dollar would run counter to that, and undercut whatever credibility Cronin hopes to take into the post-Lillard era.

One of the dark-horse teams floated Saturday by ESPN's Ramona Shelburne is San Antonio, who have been on the other end of this. Cronin would do well to approach these talks the same way the Spurs did Kawhi Leonard's trade request in 2018.

Trading Leonard to his preferred destination, the Lakers, was reportedly a non-starter for Gregg Popovich and R.C. Buford, and the Lakers package that eventually got them Anthony Davis was a lot more attractive than anything Miami has to offer. The Spurs didn't like that the Lakers had spent a year working behind the scenes to recruit Leonard, or that when Leonard requested a trade his camp made clear that any team other than the Lakers would be trading for him as a one-year rental. They eventually traded him to Toronto, where he played one season and led the Raptors to a title before leaving for the Clippers, not the Lakers, in free agency.

Taking an "anywhere-but-Miami" stance is a lot easier for the Blazers when just about anyone in the league can put together a better offer than what the Heat have. Letting your star under a long-term contract dictate his destination is a lot more palatable when you're not getting fleeced. Kevin Durant only wanted to go to Phoenix at the deadline, and it eventually happened because the Suns had real assets (Bridges, Cam Johnson and a large volume of picks) to offer Brooklyn. The Thunder got a massive haul of picks plus Shai Gilgeous-Alexander from the Clippers for Paul George and everyone came away happy.

The "everybody wins" scenario is not possible with what Miami has to offer the Blazers. Somebody is going to lose there, and that somebody is going to be Cronin. So far in his tenure, he hasn't lost many deals because he hasn't made many deals. The Lillard deal is the one he'll have to make eventually, and for the sake of the franchise he'll be tasked with rebuilding, it's the one he can least afford to lose.