In the spring of 2022, Damian Lillard stated emphatically, and for approximately the 5,348th time, that he wanted to stay with the Portland Trail Blazers. No one doubted it. Because if there’s one thing we’d learned over the years, it’s that Damian Lillard is fiercely loyal to the team and city that drafted him.
In the spring of 2023, Lillard reiterated that commitment—for approximately the 5,349th time—but then, surprisingly, he also entertained two hypothetical trades: to Miami, where he could play with Bam Adebayo (“my dawg”), or to Brooklyn, where he could play with Mikal Bridges (“my dawg, too”). This also seemed reasonable. Because if there’s one thing we know about Damian Lillard, it’s that he’s fiercely loyal to his friends, especially the friends who are as passionate and driven as he is.
In July, word leaked that Lillard had, at long last—after years of dithering by the Blazers front office—demanded a trade and that, further, he would accept just one destination: Miami. Any other outcome, anonymous sources threatened, might prompt a messy holdout. The market froze. There would be no robust bidding war for one of the game’s all-time greats. Dame-to-Miami was sold as an inevitability, a fait accompli—and never mind that the Heat had few assets the Blazers actually wanted.
Last week, Lillard was traded to Milwaukee—which is not Miami—a deal that shocked the entire basketball world because it defied everything we’ve come to expect in today’s NBA, where the superstars generally get what they want—and where and when they want it. If a star of Lillard’s standing wanted Miami, and only Miami, well then, of course he’d end up there. Fans believed it, pundits promoted it, and executives across the league expected it.
So with all that shock came another sentiment from other team execs: relief. Superstar empowerment, it would appear, still has some limits.
“Teams are taking back control,” said an Eastern Conference executive, a stance echoed by several others last week. “It is a significant event that [Lillard] didn’t land where he wanted,” said another longtime GM.
Indeed, the Lillard trade might signal a new subtle shift in NBA power dynamics.
The Blazers’ stubborn stance—which was widely excoriated all summer—has been thoroughly vindicated by the pieces acquired in the initial Lillard deal, plus Sunday’s follow-up trade, in which Portland rerouted Jrue Holiday to Boston. The total return for the Blazers so far: Deandre Ayton, Robert Williams III, Malcolm Brogdon, Toumani Camara, three first-round draft picks, and two pick swaps. They could conceivably keep adding to the draft-pick stockpile by re-trading Brogdon and/or Williams.
It’s a far better outcome than anything the Heat could have offered, which is why rival executives are almost uniformly praising Portland’s approach.
Two testy standoffs dominated the offseason, with a disenchanted Lillard staring down the Blazers and a disgruntled James Harden demanding the 76ers send him to the Clippers (and only the Clippers). In both cases, the teams held firm. “We are going to do what’s best for the team,” Blazers GM Joe Cronin declared in early July. Two weeks later, 76ers president Daryl Morey said of Harden’s demand: “If we don’t get either a very good player or something we can turn into a very good player, then we will just not do it.” Harden, as of this moment, remains a reluctant 76er.
Many rival execs are quietly applauding. It’s not that they begrudge players the option to choose their own path; no one is arguing against free agency or player autonomy. But superstar trade demands are now so rampant, so routine, that it’s become almost destabilizing. There have been 14 in the last five years, including three by Harden.
Teams can’t plan with any certainty. One star’s mood swing can alter the course of a franchise and the league’s balance of power—to say nothing of the impact on disillusioned fans. And the stars keep pushing the envelope to new extremes. First, the trade demands came with a year left on their contract, essentially an early courtesy to the team: Trade me now, or lose me to free agency (see Kawhi Leonard in 2018). Now, stars routinely ask out with multiple years left: Paul George in 2019, Ben Simmons in 2021, Lillard this year. Harden demanded a trade while opting into his contract.
Not long ago, stars would provide a list of three or four preferred destinations, giving their team multiple potential trade partners and a chance to extract the best return. That’s given way to the “one team only” demand—see Lillard and Harden this summer, and Kevin Durant (Phoenix) last season. Even team executives who otherwise support player autonomy draw the line here.
“You can’t get the contract that you want and then restrict the team from being able to extract the value of the contract if you’re not going to play [for them],” said a veteran Western Conference executive. “You can’t have all of it. None of us can. Teams must be able to maximize the values of the contracts they sign. But the hope is you’re able to do this in a way that’s in coordination and communication with the player and the agent, and it doesn’t turn adversarial.”
The one-team-only demand can occasionally work out for the franchise that’s losing its star—the Nets, after all, got a massive haul from the Suns for Durant last February. But confining the market to one destination can also destroy a team’s negotiating leverage, making it close to impossible to get fair value. It’s why it took nearly three months for the Blazers to find a palatable Lillard deal. It’s at least in part why Harden is still stuck in Philly.
“I would have never done that, for all [those] reasons,” a veteran NBA agent said of Lillard’s Miami-or-bust demand. “These [GMs’] jobs are on the line; he’s going to have to answer to ownership. Even if Joe [Cronin, the Blazers GM] wanted to do right by Dame, he had to drag it out and see how much he could get out of Miami, or to get Dame to bend and say, ‘You know what, I’m open to other teams.’”
Had Lillard’s camp listed multiple teams from the start, the Blazers could have generated competing offers and perhaps resolved the standoff much sooner. And, the veteran agent noted, “I think his chances of ending up in Miami would have been much greater.”
A necessary reminder: The superstar empowerment era began with LeBron James’s decision to leave Cleveland for Miami in 2010 … as a free agent. The “empowerment” part was about using free agency to choose his own destiny, rather than to feel bound by some quaint notion of loyalty to the team that drafted him. A wave of stars followed his example.
But then came the trade demands. Carmelo Anthony, Chris Paul, Dwight Howard, Paul George, Kyrie Irving, Chris Paul (again), Jimmy Butler, Kawhi Leonard, Paul George (again), Anthony Davis, Russell Westbrook, John Wall, James Harden, Ben Simmons, James Harden (again), Kyrie Irving (again), Kevin Durant, Damian Lillard, and, uh, James Harden (again!).
Another wave is inevitably coming. Maybe it’s Joel Embiid. Or Luka Doncic. Or Donovan Mitchell. Or maybe, if the Lillard gambit fails, it’s Giannis Antetokounmpo. Rival GMs are monitoring them all.
Trade demands are now as woven into NBA culture as the stepback 3 and the Red Panda halftime show. We’ve essentially grown numb to them. Almost.
“In terms of trade demands, of course, [we] don’t like them,” commissioner Adam Silver said last month following a recent board of governors meeting. “As a league, we want players—and teams—to honor their contracts. I’m watching both the situation in Portland and Philadelphia and hope they get worked out to the satisfaction of everyone before the season starts. I’m glad that things seem to have settled down somewhat, at least in terms of public discourse.”
Player contracts have always come with an implicit trade-off—financial security over career flexibility. Want maximum security? Sign a longer contract. Want more freedom? Sign a shorter one. Want out? That’s what free agency is for. Or, at least, that was the old model. Now, superstars want both the lucrative contract and the option to choose a new team at any time. It even has a name: “pre-agency.”
“We’re going to see more Dame situations across the league,” said one longtime GM. “With this generation of basketball players, it’s very common to switch high schools, to switch AAU teams, it’s very common to be in the transfer portal [in college]. It’s like we have a big band of [nomads].”
The league can’t change human nature, or persuade über-wealthy athletes to be more patient. Nor can league officials legislate away the issue—at least not without the consent of the players association, which is highly unlikely. So the demands will keep coming, and more often than not, teams will accommodate them. But at least in this moment, the teams are trying to wrest back a little power.
“The owners are asking the players to live up to the contracts they sign,” said a Western Conference executive. “And I think the owners are getting support from the league office.”
Anyway, “losing” the stare-down with Portland didn’t turn out so badly for Lillard. Sure, he didn’t land in South Beach and won’t get to play with his buddy Adebayo. But moving to Milwaukee, to the best team he’s ever played on, to play with a two-time MVP in Antetokounmpo, gives Lillard the best shot he’s ever had to win a championship.
Within minutes of the trade’s completion last week, Lillard tweeted his gushing approval: “Excited for my next chapter! @Bucks.” Which, really, should surprise no one, because if there’s anything else we know about Damian Lillard, after 11 seasons, seven All-Star selections, and countless clutch shots, it’s that he’s a class act and a consummate pro who wants, more than anything, to win it all. And wasn’t that the point of the exercise?
