Breakups are Never Pretty

Unpacking the fallout from Damian Lillard's contentious exit from Portland.

Even before the story published, the omission from the thank-you letter was glaring.

Damian Lillard's three-tweet, nine-slide, small-print farewell message to Portland and the Trail Blazers thanked 39 people by name. These included former coaches, teammates, behind-the-scenes team staffers, media members (including me, which was a bit of a surprise), owner Jody Allen and dozens of others.

The one name missing from the exhaustive list of thank-yous was the person who 24 hours earlier made the trade sending Lillard to Milwaukee: general manager Joe Cronin.

That snub was just a warning shot for the story published on Bleacher Report minutes later by Chris Haynes, Lillard's closest media confidant dating back to his rookie season in Portland. In a new interview, Lillard detailed his complete lack of communication with Cronin this summer following his July 1 trade request.

Cronin hasn't spoken to reporters since a July 10 press conference in Las Vegas where he admitted he "failed" in building a contender around Lillard but stressed patience in getting a trade done. He's expected to talk this coming Monday at media day. Amid the intrigue around Scoot Henderson, most of the attention will be on the breakup between the franchise and its all-time leading scorer, which has now become much more public than either side hoped it would.

Like all breakups, especially in relationships this long, this one is complicated. Lillard and Cronin are two people that are more similar than they are different. It's why they were as close as they were until the weeks leading up to the draft in June, but it's also why the partnership ended the way it did.

Both Lillard and Cronin care about not being viewed as the bad guy. Lillard has built his entire public persona for the past 11 years on being "the loyal superstar," while Cronin has sold himself as the face of a friendlier, more inclusive organization in the nearly two years since his predecessor, Neil Olshey, was fired for fostering a toxic workplace environment. It's why Lillard could never bring himself to go through with asking to be traded in previous years, even when he came close in the summer of 2021. And it's why Cronin would have never proactively traded Lillard to kick-start a rebuild, even if there was an on-paper argument that that was the smart team-building move.

For a while, their goals were the same. The two-year, $122 million extension Lillard signed last summer—which Olshey had been reluctant to offer him—was a show of faith in Cronin after the new GM had kicked off his first offseason in charge by trading for one of Lillard's close friends and long-desired teammates, Jerami Grant, and signing fellow Aaron Goodwin client Gary Payton II in free agency.

Even as last season began to go sideways after a hot start, Lillard and Cronin remained in lockstep. They would often sit courtside together for 30 or 45 minutes at a time before games and discuss the roster. At the trade deadline, after the Blazers traded Payton and Josh Hart for picks and young players, Cronin said, publicly and privately, that he was preparing to be "ridiculously aggressive" in making win-now upgrades and that he felt "extremely obligated" to put a contending roster around Lillard. Lillard was on board with the short-term step back if it meant better assets to move in the summer.

He was less on board with the end-of-season shutdown, a blatant tank job by the organization that saw him miss the final 10 games of the season with what was officially called a calf injury. At their exit interviews following the last game of the season, Cronin doubled down on his desire to make upgrades, while Lillard made clear he was not interested in going young.

When Cronin—whether by his own fault or not—wasn't able to turn the No. 3 overall pick into another star and instead drafted point guard Scoot Henderson, it was a moment of clarity for Lillard that the decision had been made for him. Yet, even then, with Lillard's confidence in Cronin fading and Cronin facing mounting pressure to pick one direction or the other, both sides still wanted to make it work. Cronin convinced Lillard and Goodwin in a June 26 meeting to give him a few more days to make something happen. That "something" never came.

The whole thing had the feel of a relationship both people knew was over but neither wanted to be the one to break it off. Once Lillard finally asked out, and asked for one specific team—Miami—that had limited trade assets, that was the end of any collaboration on a landing spot.

Where it became ugly and personal was when Lillard's future evolved into a battleground for his general manager and agent. Goodwin was motivated to prove he could strong-arm his most high-profile client to the team of his choosing despite the limited leverage of four years left on his deal, the way the bigger agencies like Klutch and CAA have been able to do for their stars. Cronin, still new to the big chair and suddenly tasked with making arguably the most important trade in franchise history, was staking his career on being able to prove he wouldn't be pushed to take what he felt was a subpar return from Miami with no other options.

From the beginning, Goodwin pulled out all the stops to poison the well for any team besides the Heat that wanted to trade for his client, to the point that the NBA league office warned him in late July to cut it out. Early leaks out of Lillard's camp that he wouldn't report or would hold out if he was traded anywhere besides Miami were largely laughed at in league circles because they ran so counter to who Lillard has been his entire career, the reason he's as beloved in Portland as he is.

If Goodwin miscalculated the NBA's willingness to believe that Lillard was capable of "pulling a Harden," his bigger miscalculation was of what Cronin viewed as the stakes for the deal he'd make. His reputation as a lead executive had already taken several hits after he punted the trade deadline and wildly overpromised both Lillard and fans after the season about taking big swings on win-now talent only to come up empty. Caving to a public campaign to send Lillard to Miami for limited assets would have ensured he won't be in the job for much longer. Not only would it have set the Trail Blazers franchise back, it would have set a precedent that a star player with four years left on his deal could force his way to any destination regardless of what came back. If that went on Cronin's resume, he was never working in the NBA again, and he knew it.

So Cronin, in his own way, went scorched-earth, if not as publicly as Lillard and Goodwin did. He refused to take Miami's calls and completely froze them out of all Lillard trade talks, even as the Heat front office attempted to work with third and fourth teams to come up with deals that would land the kind of assets he wanted. More significantly, and more damagingly, he also cut both Lillard and Goodwin out of the loop on his negotiations with other teams.

One thing about Lillard, for as long as I've known him, is that you'll always know where you stand with him and he wants to know where he stands with you. That was never an issue between him and Cronin until late June, when it became clear the Blazers were committed to using the third pick rather than trading it. Once Goodwin went public with the "Miami only" stance, Cronin clearly decided the only course of action was to handle business without their input. You can understand why, in his mind, that may have been the right approach to take. But on a human level, it was the wrong one. The trust between them had already eroded, and now it was completely gone.

Is it any real surprise, then, that at their early-September face-to-face meeting, Cronin didn't agree that Lillard coming to camp like nothing had happened would be a viable path forward? Would anybody have thought that was a long-term solution, or that the questions and attention around the situation would dissipate? I've written before—and told people in the organization directly—that I thought the optics of asking Lillard to stay home would be worse than the optics of an awkward media day and training camp. Not that it matters, because the two sides mutually agreeing to keep him away from the team likely wouldn't even be allowed under the league's new Player Participation Policy.

If Portland couldn't find a deal this week, there would have been no choice but for Lillard to practice and play for an organization that had already made clear they were going in a different direction. He would have put on a good face and tried not to make it weird, but that's an almost impossible task in the current social-media climate. The questions would come from new reporters at every road game. The body-language analysis would be off the charts. And even if it wasn't a full-season or long-term solution, would it make Cronin more motivated to come to a deal with Miami? Evidence suggests not.

Cronin made his bed by cutting off communications during the summer and making the relationship irreparable from his end, just like he made his bed in the spring by telegraphing his desire to make big upgrades so loudly it completely short-circuited the reasonable trade market and ultimately led to Lillard's trade request. And if Lillard is upset he isn't in Miami, he should take a hard look at his agent's handling of the summer. From both sides, it didn't have to go this way.

In the end, they both tested each other one too many times and finally pushed one another to the breaking point. Cronin thought his strong working relationship with Lillard would be able to withstand drafting another point guard after promising to make upgrades. And Lillard and his representation thought they could back Cronin into a corner and get him to Miami. They all thought wrong.

The great irony of this summer's ugliness and bad feelings is that both Lillard and the Blazers come out of it in much better positions than they were in at the end of the season. Lillard didn't get to Miami, but he wound up in an even better basketball situation in Milwaukee, and now has the best chance to contend that he could ever hope for. And Cronin has a pretty enviable starting point for a rebuild with Henderson, Shaedon Sharpe and Deandre Ayton.

Lillard's first game in Portland as a visiting player will be on Jan. 31. There will be all the fanfare and tribute videos that usually come with those occasions. Will he and Cronin make up then? If the Bucks are at the top of the east and Henderson is as good as the Blazers think he will be, maybe. Eventually, they'll get past it. If Lillard gets a ring in Milwaukee, he'll forgive Cronin for the communication breakdown once he made the Miami demand. If Cronin's rebuild is going well, he won't worry too much about Goodwin's scare tactics and Lillard's coordinated tell-all interview dropping at the exact same time as his public thank-you letter.

In the moment, this stuff always feels worse than it is. Earlier this summer, I researched media coverage of Bill Walton's and Clyde Drexler's exits from Portland. Both were much more contentious than this summer has been, with the difference being the lack of social media amplifying everything. And Lillard has much stronger ties to the city and community than either of them did.

The last line of that goodbye letter:

"I do believe a day will come when I put a Blazers uniform on again, and hopefully by then I'll be forgiven for breaking your hearts along with my own."