How Long Will the Damian Lillard Trade Process Drag Out?

On July 2nd, 2023, Damian Lillard officially requested a trade from thePortland Trail Blazers. It’s now July 25th and...still no trade. For Trail Blazers fans, this is a little bit like waiting for surgery. You don’t want to do it. You wish it weren’t happening. But if we have to go through this could we just get it over? How long is this going to take, anyway?

That’s the subject of today’s Blazer’s Edge Mailbag.

Dave,

I read/hear a lot about how long it’s taking to make the Dame trade — it really hasn’t been that long since the request, especially given it’s the off season and not much else is happening. Miami has some potentially valuable young assets that just aren’t available to be traded yet because of when they signed their contracts (Jaime Jaquez Jr., Orlando Robinson). I don’t know that the Blazers are interested in these players but do you think that is a factor in this not being done yet? Could a deal be established but not revealed because it can’t actually happen yet? I would have thought I’d see more theorizing about this possibility.

Sara

It’s theoretically possible. I don’t think it’s a major factor, though. Those signings are 100% guaranteed to happen. They would not be holding up the proceedings as an unknown variable. If Miami and Portland were simply waiting for rookie ink to dry, we’d have heard it by now. “This deal is done and will be consummated when those contracts are signed...” Instead of that, we’ve gotten silence.

That is not necessarily a bad thing from Portland’s point of view, though. As long as Lillard insists upon going to the Heat, Portland’s only play is to extract the most possible benefit from Miami in return. With each franchise looking out for their own interests, the only way that happens is if the Blazers maintain at least equal power, if not greater power, in the negotiations.

One of the oldest and truest maxims of bargaining is that whomever wants it more, loses. This is why used car salespersons try to convince you of the value of their vehicle, claiming that six customers are lining up to buy it in the next hour if you don’t. They’re trying to generate desire, plus fear of missing out. They know that once you’re salivating for the ride, they can extract maximum return for it. You can only get it from them (and quick, before it’s gone), but they don’t necessarily have to sell it to you. Cha-ching! Because of that power imbalance, you’re going to pay.

We know Miami wants Lillard. Who wouldn’t? We also know Dame wants to go there. The relative silence on Portland’s part (so far) establishes the Blazers as the party that isn’t sold on the deal, that has to be convinced, and thus has the superior bargaining position. This is critical, as it’s theonlypower Portland has in this scenario. Otherwise, they’re just a bunch of poor jerks being jilted by their franchise superstar, unable to even explore alternative offers for him.

It’s also likely that, from the start, Miami has attempted to grab the upper hand in negotiations using some version of the question, “What do you want for Dame?” Framing the question that way establishes, and centralizes,Portland’sdesire for the deal.

This is exactly like our car dealer saying, “What’s your budget for your next vehicle?” Once you name that price, you’ve ceded all control to them. With your offer established, they’re going to charge you that amount, and a bit more, for anything they bring out, giving you as little as possible for your stated price. Your buy-in is set in stone, theirs is flexible.

The tug-’o-war at the heart of this drama isn’t over who gets Dame, it’s over who gets to be the dealer and who’s the customer as the deal gets negotiated. Understanding that, Portland’s best stance with Miami is, “We don’t come to you with offers. You come to us. We still have the player you want. It’s up to you to bargain for him, not the other way around.”

The Blazers want to establish that they have the car that Miami wants (Dame), forcing them to haggle for price. Miami wants to claim that they have the vehicle (the deal mandated by Lillard’s trade request, which somehowhasto get done), making Portland negotiate to make the best of it.

波特兰需要保持p的权力关系lace, not letting Miami flip the script. Like the car dealer, Portland’s can’t perspire at the table. Make the Heat do the legwork. Get them to express their desire and act out of urgency. Don’t show any indication that you need to make this deal, want to sell the car today, or even care if you sell it to them. Make Miami come knocking at the door with a proposal,just like any other team that wanted to trade for Dame would.If they don’t, be quiet until they do.

Naturally, this drags things out. To make sure they keep their place at the table, the Blazers will be willing to live with quiet and delay, to a point. If I had to guess, I’d say this is the source of the delay rather than any magic date at which assets will come available. Each team is waiting for the other to walk into its showroom.

Several things could break that stalemate.

First, though not foremost, Portland wants to get this deal done too, given the circumstances. We haven’t mentioned it enough, but I believe Joe Cronin and the franchise do feel a connection with Dame, respect his position, and would like to see a successful outcome for him. They just don’t want to get screwed over in the process.

The Blazers have a few incentives to move quickly, or at least before summer is done. They will face PR and team chemistry issues if Lillard is still with the team on opening night of the season. They can disguise his presence through training camp and preseason...not completely, but well enough to keep the circus manageable. As soon as he takes the floor in a regulation game and faces mandatory post-game press conferences, the zoo is going to run amok. Portland won’t ruin the future of the franchise to avoid temporary chaos, but if they can get a deal done before then, they will.

Obviously the Heat would like Lillard in the fold well before that point too. Ergo, Opening Night going to be your big-picture deadline.

Team officials generally take extended vacation in August (though the gravity of the Lillard situation may cause them to keep the phone near anyway). If a trade hasn’t been made by September, I expect talks to heat up then.

Failing that, December 15th is the first day that free agents who signed contracts this summer can be traded. January 15th offers the same potential for free agents who re-signed with their current teams via Bird Rights and got big raises. These dates will open up more trade possibilities in multi-team deals.

Then, of course, we have the 2024NBA Trade Deadlinenext February. It’d shock me if a deal took that long. By the time Miami butted up against the trade deadline, they probably would have given up on the notion.

No matter how long the negotiations last, it would also shock me if the relationship between the Blazers and Lillard went south in the meantime. If he’s still in Portland come October, I’m guessing he’ll suit up. The whiplash effect of going from face of the franchise to getting suspended for refusing to play is huge...too striking to imagine. Souring the relationship at the end doesn’t help either party.

If Lillard does consider sitting, though, we need to circle another date roughly halfway through the season. Dame is scheduled to make roughly $45 million this year. If he sat out and was suspended, he’d lose $21 million right around the 38th game of the campaign.

That number is significant because it’s speculated that at least part of the reason Lillard favors the Heat above all other contenders is Florida’s lack of income tax. Oregon’s rate is right around 10%. In Miami, it’s zero. To you and me, the difference is annoying. Given the years remaining on Lillard’s contract, it amounts to a cool $21.6 million extra for him, just by moving to Florida.

(Mandatory Caveat: I’m not a tax expert. Players may well fall under the tax laws of the states they play road games in too. But the general idea is sound even if the numbers aren’t comprehensive. Lillard saves lots of dollars by going to Miami.)

If Dame were to sit out, any financial advantage of getting traded would evaporate by Game 39 of the season. He’d lose the same $21 million he would have gained. He’d never make the money back. At that point, one of the presumed benefits for the move would be gone.

This is why chatter about Lillard pushing the nuclear button seems far-fetched to me. For financial reasons alone—let alone PR goodwill and endorsement exposure—playing in Portland makes sense, even if the marriage is unhappy. Unless something deeper is going on or someone gets a huge case of The Stubborns, sitting out is a non-issue

Wrapping up...all parties involved want this deal to be consummated successfully. They just have different definitions of success. They’re spending the early stages of the negotiating process jockeying for position and the power to preserve their own prerogatives. That’s making things slow.

Once momentum picks up, be it with Miami or another team, my guess is that a trade will happen quickly. I’m also guessing that we’ll know whether a deal is going to happen well before the season starts. Either that, or this issue is going to go bye-bye for a couple months and pick up steam again in January.

Thanks for the question! You can always send yours to blazersub@gmail.com and we’ll try to answer as many as we can!