Damian Lillard was traded to the Milwaukee Bucks on Sept. 27th in a three-team trade.

Has the NBA’s Player Empowerment Era hit its ceiling?

That’s what I’m wondering as the Damian Lillard and James Harden situations drag on into extended standoffs between player and team, with no sign of resolutions anytime soon.

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While the specifics of each case differ, they share three commonalities: a player demanding a trade, specifying one specific team as his desired destination (Miami for Lillard, the Clippers for Harden) and doing so despite very recently binding themselves to their current teams for longer.

Harden opted into the final year of his contract at $35.6 million in June, when he could have become an unrestricted free agent. Lillard signed a two-year, $122 million extension with Portland in July 2022; he could be an unrestricted free agent this coming summer if he hadn’t, and presumably have significantly more leverage as a result.

This is all part of a larger story arc, as the last several years have seen increasingly aggressive efforts by players to navigate themselves to their preferred situations despite suboptimal leverage. Once upon a time, it was just players in the final year of their contract — or maaaybe midway through the season before — who pushed their way out like this. And once upon a time, they would come up with a list of teams, not just one specific place they demanded to be sent.

Read more: What led to Damian Lillard’s trade from Blazers to Bucks? A timeline of the saga

However, players steadily kept succeeding with this despite the worsening leverage positions from which these maneuvers were attempted — even with more years left on their deal or fewer teams on The List, they still got their way.

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Still, it’s important to note the distinction between recent events and what is occurring now. It’s one thing for Anthony Davis to demand a trade to the Lakers when they had the cap room to sign him outright after the season. In a different vein, it’s one thing for Paul George to ask for a trade to the Clippers even though he had several years left on his deal in Oklahoma City, when the Clippers were highly motivated to overpay for his services at that moment given that he’d bring Kawhi Leonard with him.

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It’s quite another to, say, demand a trade to the Heat with four years left on your deal and no deadline to compel a quick decision. Or to demand to be sent to the Clippers, and only the Clippers, when they really don’t have much to send back that would be useful for Philly right now.

The mindset driving this change could be described in three words: Get that bag. Elite players realized that they could navigate themselves to desired destinations without ever having to become free agents. As a result, they could significantly reduce their financial risk by continuing to sign rich extensions the moment they were eligible, knowing they could always push their way out later.

In theory, at least.

In practice, this approach has a nagging fly in the ointment: The team is not actually required to trade you anywhere, at all, let alone to the lone team on your wish list.

The team can do this because it doesn’t like the other team’s offer, or because it thinks it can do better if it waits, or because it just doesn’t feel like it. The why almost doesn’t matter: The important part is that the player is under contract, so if the team won’t play ball on a trade demand, the player can’t do much about it.

We saw bits and pieces of this play out two years ago when Ben Simmons’ trade demand dragged on into eternity. We got another taste last summer when Kevin Durant’s trade demand ended with him returning to the Nets … at least for a while.

Durant, like Lillard, had multiple years left on his deal and wasn’t able to get his wings until a new owner took over the Suns days before the trade deadline and immediately gave Brooklyn everything it wanted with a cherry on top. Simmons, meanwhile, was a test case of whether an NBA front office would have the gumption to let a trade demand fester into the season rather than take pennies on the dollar to get it over with. The Sixers’ answer was the latter, and ironically, it ended with a steal of a trade to acquire Harden.

Again, Harden helped create the current impasse in Philly by completely whiffing on his high-leverage moment earlier this summer. Harden could have become an unrestricted free agent and threatened to walk away from the Sixers for nothing — a much-talked-about Rockets reunion, for instance, had been rumored for several months.

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It might well have been a bluff, but it was also the one tangible way for Harden to force an opt-in-and-trade to the Clippers. Whatever expiring nonentities the Clips might have offered Philly for Harden was still likely to be better than losing him for nothing. (If you’re wondering, signing-and-trading Harden to the Clips wouldn’t have worked under the new CBA without major salary shedding.)

Now, the leverage is gone. Instead, Harden opting in leaves the Sixers highly incentivized to play the long game; the trade deadline is the only upcoming leverage point, and it’s still six months away. By then, a lot of water could go under the bridge and other teams’ situations could change, leading Philly to a more plausible end game than the dead ends currently available. The Sixers already saw this play out before with Simmons.

Additionally, the Sixers backstopped themselves by making the worst-case scenario of losing Harden for nothing in 2024 free agency a potentially survivable option. Philly can have max cap room — actually, even more than max room — after the season and seemingly will pass on an extension for Tyrese Maxey to keep that in play.

It’s a risky play but could it bring another star to Philly? While extensions are likely to take several names off the market before next summer, at the moment, George, Leonard, Pascal Siakam, Jrue Holiday and O.G. Anunoby could be unrestricted free agents on July 1.

(Counterpoint: If those players all extend, the three best free agents on the market could be … Harden, Maxey and Tobias Harris.)

As with Simmons, Harden’s best ploy in the meantime is not to hold out — which would result in the team being able to withhold pay — but instead to show up and be such a distracting, wearying pain that the team will do almost anything to be rid of him. Copying Durant’s “Insult the GM” tactic is a start, but this will require a sustained effort.

Alas, this is a bit riskier when you’re in your age-34 season and on an expiring contract. Harden’s ideal end game here is to play well and secure one last giant bag, not to roll into a 9 a.m. shootaround straight from the club.

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As for Lillard, it’s sort of a bizarre ripping of the Band-Aid after the Blazers spent the last two years pretending their best move was anything other than trading him. Now that they landed Scoot Henderson in the draft, they have a backcourt of the future and a clear runway into the rebuild. Lillard, if anything, gets in the way of that by making Portland too good … something the Blazers solved last season only with brazen spring tanking and good lottery fortune.

Thus, trading Lillard is clearly the logical move for the Blazers … but on their timeline, not Lillard’s, and not necessarily to the team of Lillard’s choosing. As with Harden, Lillard’s leverage is basically limited to threatening to be an insufferable jerk if he’s not in the city of his choosing, because he still has three years left before he can become a free agent.

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Additionally, the Blazers aren’t in win-now mode the way Philly is. As a result, “Trade me or else” is easily greeted with a shrug and “Or what?” And in this case, Lillard holding out would actually be helpful for the Blazers, as he’s likely the only thing standing between the Blazers and another high lottery pick. Portland has time on its side to wait for the best offer, even if it drags into the trade deadline or beyond. Lillard gave up his opportunity for leverage when he inked the extension.

How will it end? We don’t exactly know. Durant and Simmons eventually got their wings, but only after tortured half seasons in Philly and Brooklyn, respectively. Lillard and Harden would seem to have limited trade markets beyond the teams they’ve targeted, which could help them ultimately get their way. On the other hand, there’s no rule requiring the Blazers and Sixers to trade them to their preferred destinations … or at all.

The last several years have seen several star players wriggle themselves out of situations they wanted to exit, but few had as little leverage as Harden and Lillard appear to have right now. How these play out will be fascinating case studies on the boundaries of the Player Empowerment Era … and important benchmarks for future NBA stars (and their agents) contemplating their own exit strategy.

(Photo of Damian Lillard and James Harden: Eric Hartline / USA Today)