Damian Lillard: Trail Blazer for Life?

All-Star guard Damian Lillard is the heart and soul of the Portland Trail Blazers franchise. His impact goes beyond just 26.9 points per game. He’s a public relations machine, internationally recognized, and on the marquee of every arena the Blazers visit. He’s an anchor point for selling tickets, Portland’s most popular jersey selection...a true star in a town that hasn’t sported many of them. Lillard’s contract also expires in the Summer of 2021. As that date approaches, his status with the Blazers is coming under scrutiny. That’s the topic of the Blazer’s Edge Mailbag today, the first of a two-part piece considering various possibilities ahead of the Blazers.

Greetings brother Dave,

Here’s a six-pack of questions. Please give me a percentage you think of the likelihood and a short explanation.

1. Damian finishes career in Portland?

As you’ve noted, questions like this run on a probability continuum. I don’t like speaking in certainties (because nobody knows them) and I don’t like speaking in percentages much either (because they become a covert way of predicting certainty, only cited in hindsight). Especially when speculating on the future of players, it’s ultimately their choice to sign a contract or not. We’re not in their heads right now, let alone in future space when these decisions will be made. To claim otherwise seems pompous.

Instead, with your permission, I’d like to think of this as an environmental bell curve surrounding the player. Things in the low-probability edges of the curve one year drift into the higher-probability fat part in subsequent years, not just because the player has changed his mind, but because the landscape has changed around him and the view is different.

No curve has shifted more obviously from 2017 to 2018 than the one labeled “Damian Lillard for Life”. A couple years ago Lillard professed undying loyalty to the Blazers. I applauded that, but also cautioned that he shouldn’t be expected to stick to it. NBA career opportunities look different at 30 than they do at 25. Still, as recently as last summer, those proclamations—combined with Portland’s obvious stake in retaining Lillard—made him a decent bet to stay.

Ed Davis departing, the team’s emphasis on youth, and multiple years of questionable (or barely significant) free agent acquisitions appear to have changed the tune. Lillard’s comments this summer have skewed towards muted or subtly negative. That’s not a dramatic change from last year—he had already shifted into neutral then—but it’s a big move from the comments of a few years back.

To be fair, some of this was going to happen naturally as Lillard’s contract moved along. If the Blazers were knocking on the door of a title, the story would be different. But the more Dame ages, the more no progress will look like negative progress. It’s like eating the same pasta six meals in a row. Spaghetti isn’t bad, but somewhere around Day 5 you start thinking a steak would be nice.

The odds of Lillard becoming enthusiastic enough to re-up when his contract ends pretty much mirror the odds of the team getting dramatically better before he has to make that decision. Consider him an accomplished chef. Will management give him the opportunity to head the restaurant of his dreams, or will franchise remain the equivalent of IHOP with a three-star chef flipping pancakes the kitchen?

Up until this year, that question was up in the air. The Blazers needed multiple summers to evolve; Lillard’s contract seemed infinite. “Wait and see” was enough to keep things together. In August, 2018, Portland has had their chances and Lillard’s time is getting shorter.

Two off-seasons remain before Lillard makes his decision. As things now stand, the Blazers will be capped up in the first. The same will hold true in the second unless they drop Al-Farouq Aminu. They lack quality trade assets. They just don’t have enough time or resources to make a turn-around probable.

Most players in Lillard’s situation, looking at unlimited options with a short career remaining, will go where their gifts can be used best. That’s not likely to be a team in Portland’s situation.

Both parties have options. Lillard could ink a short-term contract with Portland, keeping him in town another couple years, then re-evaluate when he’s 32. The Blazers could super-ultra-mega-max him and hope the money makes a difference. (It might make up for having to rebuild from scratch around him.) Or maybe Lillard’s fondness for the city and the franchise will win out in the end.

The key to all of those situations is they’re not ideal. They’d take stretching, an accommodation on Lillard’s part. Technically, Lillard is not required to stretch. He’ll be able to write his own ticket. The Blazers will have to be nervous about his potential to do so. As 2021 approaches, they’ll need to consider the possibility of trading him rather than watching him walk away for nothing.

For all these reasons, the probabilities have shifted. The professions of loyalty that anchored the “more likely to stay forever” assertion are becoming less relevant, both because of their distance in time and because of the changing environment. Once that line of thinking occupied the fat part of the bell curve. That’s no longer true. Nothing is certain, but from a detached point of view, superstars in Lillard’s position are more apt to finish their careers somewhere else than they are to stay. The Blazers are more likely to head into a rebuild without Lillard than they are to build a championship contender around him or to convince him to forego the chance to win one.

We’ll tackle Daryl’s five other “probability” questions in the next Mailbag installment! You can send your questions to blazersub@gmail.com if you wish!

—Dave / @davedeckard / @blazersedge / blazersub@gmail.com