Damian Lillard and the NBA’s Superstar Problem

Ezra Moleko
5 min readJul 11, 2023

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Dame Time’s likely up for the Portland Trailblazers.

NBA fans have quickly become acquainted with the fact that every summer, at least one superstar, All-NBA caliber player will request a trade from their current situation and present a list of teams they would like to be re-directed towards. This offseason has proven itself no different, as Portland Trailblazers legend Damian Lillard has officially put his own name onto the trade block, with an incredibly short list of suitors he’d be willing to play for. We’ve often heard stars in this situation list out three to five teams they could be content to join, but Lillard’s camp has made it clear that only one team really fits the bill, the Miami Heat. It is not hard to see why, Miami is a big market, a warm beach city, and a contender in the East. It’s also not hard to imagine why Lillard may feel he has earned the right to select himself a new venture regardless of any difficulties.

As the long-time stalwart of a middle-tier small-market franchise, Lillard has put in more than his fair share of work for his current club. He’s earned seven all-star selections, seven all-NBA teams, and has led Portland to the playoffs almost every year during his tenure, despite some recent troubles. Crucially, however, the Portland Trailblazers have not done much to maximize Lillard’s opportunities to win during his prime. The team has shown a perplexing reticence to make any major change-ups to the roster until it’s been too late, despite clear evidence that the best-case scenario was not a particularly high benchmark. Blazers GM Joe Cronin has had only a year to turn around a roster which has spent several seasons stuck in mud under the watch of previous GM Neil Oshey, but the Blazers’ 25th-place record this season shows the unlikelihood of that happening quickly. Does this then mean that Lillard should have carte blanche to play hardball, including having his agent quell interest from teams which could offer better packages, or is it only another aspect in the business of this league which has become so used to the superstar trade scenario?

Lillard would be an excellent addition to a perennial contender in the Miami Heat.

Unfortunately, no matter what should happen, it’s fairly clear that the Trailblazers will wind up honoring Damian’s trade request, and it will most likely be to his preferred destination. The recent history of superstar trades has shown the potential risk of trading for an unhappy star is likely to outweigh the benefits of landing one for an interested GM. Think about it like this, if your name and job were staked on the outcome of a move like that, the only potential win scenarios are that the star becomes happier in that situation (unlikely), or that you win a championship with them on your roster, at which point they are still likely to leave and make your job more difficult. While we speak of NBA teams as “organizations”, they are not hiveminds, and internal dissent to a shake-up is always likely. Jobs are always at stake in this league, and a move like this is likely to change quite a few resumes in time. The risk of bringing in an uncommitted or unhappy superstar and the accompanying media circus inherent to that situation is too great for most front offices to stomach, especially considering Lillard’s guaranteed money on the NBA’s biggest contract. Essentially, Lillard has all the real power in this situation to dictate the outcome behind the threat of his dissatisfaction.

It’s not likely that these types of situations will stop occurring any time soon, either. It used to be considered the conventional wisdom that trade requests be made in the last or second last year of a contract, as the threat of leaving in free agency created a potential pitfall for any team that got involved which the star was uninterested in playing for. This has shifted in recent years, as the NBA’s contract incentives always favour signing with your current team for the greatest amount of money possible. Stars executing the previous method were always sacrificing an extra year and tens of millions of dollars on their contract. It’s no wonder that once Ben Simmons made the decision to request a trade with multiple years left on a brand new deal, waiting an extra year or two to re-up the max money contract became the most viable and sensible option. It’s simply profit-maximizing on the part of the star player to operate in this way when leaving their team on the table. It’s not unfair of a star to want their cake and to eat it too, but it does leave the fans squarely in the middle of a dispute they have almost no influence over. At the same time, there is a passive benefits to fans and teams alike– a player traded with several years left on their deal is likely to attract a much more fair value on the trade market than one who is expiring. Then again, when there is only one team allowed to bid on a player’s services, the compensation will almost never be fair value.

Hopefully it never gets as bad as the Ben Simmons saga again.

It won’t be long until we are forced to re-litigate this question with another small-market franchise losing its cornerstone player. This state of affairs has not resulted in an unbalanced or unfair league as one might suggest. The competitive balance in the NBA, to my eyes, has never been as great as it is now. It is, however, creating a level of pessimism in the rules of the system. For fans, why even celebrate when your favourite player signs a massive extension with your team? It only makes them more content to walk out the door at the first sign of trouble. Why even engage with the rigamarole of free agency signings when only role players really participate in the process? The NBA fan’s obsession with celebrity and trade culture has reached a peak that it’s hard to climb back down from, and it’s changing the way that teams operate to keep stars happy. Can they find a way to keep the fan happy as well, without sacrificing the 24/7 news cycle?

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Ezra Moleko
Ezra Moleko

Written by Ezra Moleko

Big time Hoophead, Biased Raptors fan, also enjoys cooking and long walks on the beach

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