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Who Has More Leverage, Damian Lillard or the Trail Blazers?

If Portland and their star go to war, what happens?

Chicago Bulls v Portland Trail Blazers Photo by Soobum Im/Getty Images

No matter what else happens this summer for the Portland Trail Blazers, Damian Lillard will remain the central topic until the day he’s traded. He’s stated a firm desire to join the Miami Heat. The Blazers have expressed and equally firm desire to get a good return for him, regardless. Who has the leverage in this situation and how might it be used? That’s the subject of today’s Blazer’s Edge Mailbag.


Why is everybody talking like Dame has the power? Don’t the Blazers hold his contract still? They don’t have to trade him until 2026 if they don’t want to. They don’t have to trade him at all, right? Nobody can force them to. Why doesn’t anybody talk about their leverage?


Power is a tricky thing. Using it is not just a question of what you can do, but what you should do. The former is cut and dried, the latter, far more complex.

Every relationship is a web. This is just as true of business relationships as personal. Recall the old stereotype of a businessman golfing with vendors and clients on a Saturday morning. He isn’t hitting the links because he loves the sport, nor because those are his fastest friends. He understands that golf, the Chamber of Commerce, and the local business breakfast are vehicles for building the connections needed to succeed.

Our stereotypical 1980’s golfer may find it necessary to sit across a table from one of his golfing buddies, bargaining hard and threatening to invoke lawyers to get his way. He’ll do it if he has to. But he’ll also understand that reaching that point in the relationship is a failure, even if he ends up succeeding in his immediate mission. No web gets stronger by punching a hole through it. That ripped spot will weaken the threads around it, and potentially the whole relationship.

If at all possible, he’ll try to reach an accord before having to rely on his economic and legal rights. Satisfying his need while keeping the web intact is better than doing it through devil-may-care destruction.

The business environment has changed from what it once was. The world is bigger. Interpersonal webs have weakened. Fewer people than ever rely on golf or the local Moose Lodge to sustain their business connections.

The NBA is still a small world, though. Count every player, agent, coach, General Manager, and owner, and you’ll end up with a few thousand...about the same number of individuals as there are businesses in a single city. In that environment, every decision by one of those members is, by default, a local decision. Nobody is packing up and moving to any other league if they can help it. They’re going to swim in the same water they work in. Nobody wants to do anything untoward in it. That’s going to float back to you. Accordingly, both Lillard and the Blazers will want to try out every option possible before resorting to force.

If it comes down to it, you’re technically right. The Blazers could spend $216 million over the next few years forcing Lillard to regret the day he opened his mouth about a trade. They could tell him to go home until he relents and is ready to play for them again. Alternately, Lillard could sit out, suspending his salary to make the point that he really, really wants out.

I think we can agree that either of those solutions would be a failure for both parties. The Blazers want to field a viable, exciting team. Lillard wants to play basketball and get paid for it. Any conclusion that doesn’t allow for both of those things to happen is undesirable. The principals could push it to that point, but they don’’t want to. Each has leverage, but the cost of using it is high.

From that assertion, you can reverse engineer the system back to the current positions of the two parties involved.

If the team suspending Lillard and/or Lillard refusing to play would be failures, sitting down across a table, engaging in multi-million dollar game of chicken would be one step from failure. The public relations cost of that conversation would be steep, too. At that point, both sides would be described as “unable to solve their differences”. Each would be expected to win or die trying. Somebody’s coming out of that conversation tabbed as a loser, dealing with a PR nightmare, having that situation hang over their head in future dealings around the league. Again, they can go into that mode, but they don’t want to.

Take one more step back. Both parties are standing in the room, side-eyeing each other and the table. They can’t go back out the door. Each side knows what the other wants: Dame to be traded to Miami, Portland to get a good deal. They also know what they don’t want: to sit down at that table and fight.

If the desires of each party were seamless with the other, this would be a done deal. Since they’re not, each one has to ask the question, “How much can I get the other to move from their stance without forcing them to sit down at the table?” It’s a balancing act. If Damian Lillard has 10 pounds of reluctance to engage in a messy war, Joe Cronin can ask for about 9.5 pounds of concessions. If he asks for 20, the scale is going to tip and the fight is on.

The trick, of course, is gauging how much desire and reluctance each party carries internally. That’s what all the posturing in private meetings and public statements has been about thus far.

Though we can’t ever read each other perfectly, two things seem evident so far:

  1. Each side has spent time and words convincing each other—and the NBA—that they are serious about their demands. Lillard really wants to go to the Heat. Cronin really wants a good deal. The reluctance to fight isn’t infinite, and evidently doesn’t weigh more than their desires.
  2. Coming at the situation like your original question did—i.e. “I have this leverage and I’m going to use it to get you to cave to me.”—is going to overwhelm that reluctance, resulting in an immediate battle. That’s exactly why this approach isn’t getting more credit right now.

With all that in mind, let’s take a moment to examine the arguments and arsenal on each side of the room and see where they might lead us.

Strengths for Lillard

Damian Lillard hasn’t come to this point quickly or accidentally. He’s been talking about improving the team for at least two years. Tempo and tone picked up in the months prior to free agency, with the team’s “promises” to him taking center stage. Since the Blazers did not pull off any draft-day trades and have signed exactly zero new free agents, Lillard can credibly claim that their pledge to him was broken. With his statements on record well in advance, there’s no reason to doubt him. Nor is there any reason to believe he’ll recant.

Accordingly, no matter what else happens, the Trail Blazers are going to take the bigger PR hit for this scenario. That’ll happen naturally, as the public identifies with superstars far more than logos, but this situation is bigger. As soon as the Blazers started tanking in March, pundits and fans anticipated the possibility of Lillard asking out. Several were openly begging for it. “The team couldn’t build around him,” isn’t going to be the final analysis. It was the opening salvo...the inarguable piece of evidence on Lillard’s side.

Two potential strikes against Lillard, commonly brought up in Portland, are not as damning as faithful fans believe.

That Lillard signed a contract extension last year matters not. Defraying a life-changing salary on the chance that he might have wanted out later would be foolish to the point of insanity. Not to mention, the Blazers were still convincing him that they’d build around him at that point. Cronin was still saying that the day after Lillard made his trade request.

If anything, increased future obligation also increases Portland’s reluctance to play hardball and eat the cost. That’s going to work in Dame’s favor, or at least not harm his cause.

Nor does limiting trade destinations to the Heat (and nobody but) hurt Lillard as much as local fans think. It makes Portland’s job harder, but that’s not Lillard’s concern.

Dame has little incentive to back down from that demand. It goes beyond affinity for Miami. He wants to go to a contender. Landing in a state without income tax could save him 5-10% of his salary, $10-20 million. Texas and Florida qualify. The Rockets, Spurs, Mavericks, and Magic are unsuitable for various reasons. That leaves the Heat. He might like other teams’ chances, but mustering $20 million worth of “like” is a large task.

When he put his name on a Trail Blazers contract, Lillard did not sign away personal desires, superstar cachet, public relations advantages, extra-contractual control over his career decisions, or his own right to make a stand. He’s using those to full advantage now.

The contract does give the Blazers the ultimate legal power in the relationship. They don’t have to trade him. But even that rings hollow.

Right now, Lillard is bigger than the Blazers. It’s not even close. Trying to keep him on board is like carrying a killer whale to work. It’s cool that you’ve got one, but what are you going to do with it and how will you get your job done?

If Lillard plays actively. his shadow will fall across every member of the young roster. Their development, their touches, their achievements will take second place to him. Knowing he’s on his way out, their careers—and any sense of normalcy surrounding them—won’t even start until he goes.

It’d be even worse in the locker room. LaMarcus Aldridge had to shut off questions about his impending free agency during the 2014-15 season to avoid this very thing. That would be a candle beside the firework of nightly Lillard questions in the media scrum.

The problem doesn’t go away if Lillard sits. The anger and frustration directed towards the franchise would be substantial. They’d experience it daily. Their names would never get mentioned without the issue taking center stage. Putting the killer whale in the broom closet doesn’t solve the problem. Office work will get subsumed in the bigger question: what are you going to do with him?

This potential nightmare would be a last resort for the Blazers. Dame knows it. His agent knows it. The world knows it. Eventually, Portland would win the protracted war, but the cost in the meantime would redefine the franchise negatively at the exact time they need positive renewal. That’s going to give Lillard even more incentive to stick to his stance.

Strengths for the Blazers

Portland holds Lillard’s contract. They may not be willing to watch him sit at home until 2026, but they can’t be forced into making a trade today. The more public pressure Lillard exerts to overcome that inertia, the less public sympathy he gathers.

Nor can Lillard sit indefinitely without giving up a huge amount of income. His base salary is one thing, but visibility and goodwill are key to his endorsement revenue. He already has to overcome anonymity playing in Portland. He’s been more than up to the task. But losing his microphone, his court time, and his athletic relevance would make him a less likely spokesperson. That won’t happen immediately, but if Lillard really were contemplating an extended sit-out, he’d hurt worse than the Blazers would in the pocketbook. His prodigious salary is only part of their cap. Those payments, and the endorsements that accompany them are 100% of his income. And the years to earn it are dwindling.

Finally, and critically, the Blazers don’t have to convince Lillard that they’re serious. They have to convince the Heat. Portland and Dame are not necessarily adversarial. If both want to move him to Miami, it’s simply a matter of getting a decent price. Neither one of them is working against that. It’s Pat Riley and company. That, ultimately, might be Portland’s way out of this situation, reuniting them one last time with their superstar against a common foe who needs to be swayed.

If Joe Cronin says, “I cannot, in good conscious, take a bad deal for a great player,” that should be understandable to everyone involved. Lillard’s camp would know that he cannot move from that stance any more than they can move from theirs.

What is Riley going to say? “We don’t think you’re worth that extra pick, Dame.” Oh really? Then why are you trading for me in the first place? And why are you my only chosen destination? And, by the way, are your fans OK with me not coming after we’ve all but said it’s a done deal?

This is doubly true if the compensation centers around future picks and third-party players. What is a 2030 Heat draft pick to Dame? If that’s the hold up, he might be expected to exert pressure on his new team to get the deal done. Who wins if the Heat and Blazers can convince somebody else to part with a prized, young player? Everybody.

This is the magic sauce that converts nobody winning at the table to everyone in the room winning together. That’s why, in the next phase of the conversation, you’re likely to see both sides move out of “convincing each other we’re serious” mode, studiously avoid any “backing off” OR “nuclear war” statements, and instead move towards talking about ways to get deals done, even if that means putting pressure on the Heat. The smartest statement that Joe Cronin could make right now might just be, “We’re committed to getting this done, but Miami isn’t cooperating.” Tossing the killer whale to the Heat’s office sure beats it flopping on the table between Dame and the Blazers, threatening to crush them both.

Thanks for the question! You can always send yours to and we’ll try to answer as many as we can!