You just can’t have your cake and eat it too.
You see, Damian Lillard has finally had enough. Every step of his career has been in service of the value of struggle. The 0 on his uniform tells the story of his life — from Oakland, to Ogden, to Oregon — of being an unexpected great. His stay with the Blazers for 11 seasons despite that team’s ups and downs has been about avoiding the “easiest” route. Lillard has been all about overcoming the realities of being a small market’s largest star in the quest for ultimate glory.
Lillard’s not the guy who wants a gifted ‘chip.
But in the end, he’s had enough of new Portland Trail Blazers owner Jody Allen’s strange mix of absenteeism and toxicity, of the front office’s confusing moves, and of a coaching staff that’s generally regarded as one of the worst in the NBA. The Blazers’ org has failed him at even a relatively low bar of support.
And as a result, he’s finally asking out of the situation he’s spent his 11-year NBA career in. You know what? That is very understandable.
The problem, though, is that Lillard holds none of the cards on the table.
At each stage of his career, Lillard has asked for and garnered the maximum extension possible. Even before his rookie deal ended, he signed a 5-year, $125 million extension in 2015. While that contract had two years remaining on it, he signed a further 4-year, $191 million extension.
The 2022 extension is the most remarkable one. While he still had three years left on that last extension, he lobbied the Blazers for and received an extra two years added on, representing his age 35 and 36 seasons, for a maximum $122 million. The Blazers agreed to Lillard’s ask, though they were initially reluctant. Paying any large amount, let alone the largest in NBA history, for a guard in their mid to late-30s has traditionally proven not to be a prudent financial move.
They did it anyway.
It makes sense that Lillard would want to get all of this financial security. $61 million per season is a huge number — the highest annual amount in a contract signed in NBA history. Lillard will make at least $400 million in his career, even ignoring his $100 million shoe deal with Adidas. This will provide for his children, his children’s children, and so on down the line. Knowing Lillard, it will pay for some great community projects as well.
But in return for that literally unprecedented financial security, Lillard gave up his leverage. Under the terms of NBA contracts, he now has to play for the team that gave him all that money — unless he can convince them otherwise.
His current tactic, though, simply isn’t very persuasive. Right now, Lillard is telling the Blazers that he only wants to go to one team: the NBA Finalist Miami Heat. In fact, his agent, Aaron Goodwin, has been “calling prospective trade partners (other than Miami) and warning against trading for his client,” ESPN reported. Goodwin confirmed the report.
“Goodwin is telling organizations outside of Miami that trading for Lillard is trading for an unhappy player,” ESPN reported. In other words, Lillard’s representation is threatening a bad locker room culture to any team other than Miami that trades for him.
It’s worth noting here, too, that Miami’s potential package for Lillard is simply not ideal for the Blazers. They have one significant promising young player they’re willing to trade: Tyler Herro, who plays the same position as Portland’s young star, Anfernee Simons. Beyond that, the Heat have just two future first-rounders to trade, and not until 2028 and 2030. Other youngsters, like Nikola Jovic and Jaime Jaquez, are late first-rounders statistically unlikely to hit. In truth, nearly any team in the league could beat Miami’s offerings here (including Utah, yes, but everyone else, too).
And so it’s here where Lillard crosses the line from reasonable to unreasonable. Lillard could have done any of the below:
• He could have chosen not to extend his contract, just as other stars have done, to become a free agent.
• He could have signed shorter yearly extensions, like LeBron James once did, to maintain maximum leverage over his future.
• He could have negotiated a no-trade clause with Portland, as Bradley Beal did, in order to control his future.
• He could have given Portland a list of multiple preferred trade locations, as Kyrie Irving or Kevin Durant did, so that their teams might be able to consummate a deal giving them a fair return, making the situation a win-win.
Lillard chose none of those. Instead, he chose, in 2022, while of sound mind, to sign a contract giving up his contractual freedom in exchange for the biggest bag in NBA history. He cannot have done both that and act like he’s a free agent and choose his single preferred location.
The Blazers presumably know this, so too does Goodwin. He, as he said, is doing “what I should for my client.” He’s trying to make leverage out of thin air, through bluff and bluster. But that’s all this is.
In the end, the Blazers should choose Damian Lillard’s next destination. After all, Lillard gave them that right 11 months ago.
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