Is Damian Lillard right to put his legacy before rings?

The NBA is a place full of casual fans and the hottest of hot takes, and few players have fallen victim to this more in recent times than Damian Lillard of the Portland Trail Blazers. A small market darling and franchise cornerstone for almost a decade, Lillard is the owner of not one but two series game-winning shots in the playoffs. Rarified air.

He was also recently named one of the 75 best NBA players of all time which, if you look at it, is pretty contentious. The aim of making it to the league is to be a superstar, make loads of money, have a signature shoe, and be recognized both in the Hall of Fame (Lillard is going in one day) and on lists like the top 75 players that recently came out. So what is the problem?

Well, it looks at this point that Damian Lillard is never going to win a championship with the Trail Blazers, and it annoys people that he’s ok with that.

Damian Lillard is the most recent, and in a lot of ways polarizing, example of what it means to fly in the face of “ringzzz” culture. The previous greats who never won a championship, such as Reggie Miller, Charles Barkley, and Karl Malone, tried as hard as they could throughout their careers to get there. With the exception of Miller, they moved around to try in an attempt to get it done.

Lillard though, much like Russell Westbrook, has a bigger picture approach. He gets to play the game he loves and be the focal point of an organization. He is happy where he is, healthy, and has a family to think about. Which really is what life is all about, so you could argue Lillard has actually figured it all out in a way that those stuck in the rat race and need for validation never do.

But there are plenty who see that as the mentality of a loser. A player happy to turn up and get paid, but also get bounced once the games really start to matter in the postseason. Is that fair? After all, Lillard has been an elite talent for a long time, and the best the Trail Blazers could muster around him were LaMarcus Aldridge and later CJ McCollum (now doing bits in New Orleans).

"“I do want to win a championship but it’s other stuff that means more to me. It’s almost like I’m not willing to sell myself out for that. When my career is over and I’m gonna know the relationships that I’m gonna have. I am going to know the people who knew I was solid with them regardless of if I was at the top or if I control it”."

That was Damian Lillard speaking to Sports Illustrated back in 2019, and although his tune changed in a more recent conversation with Bleacher Report, the main point has remained the same. Lillard would love to win, but he wants to do it in Portland and not sell out by going to a market like Los Angeles or San Francisco to do so.

Is that wrong? Will he suffer because of it? There’s no doubt that having a ring provides some kind of validation, to fans of that player at least, and we only need to look at two examples to see that Lillard’s legacy might actually be tarnished if we have indeed seen the best of him because of a troubling abdominal injury.

Chris Paul has never won a championship, and if he retires with that being the case, his previous playoff chokes will be held against him. On the contrary, Dwight Howard did win a title with the Los Angeles Lakers in the bubble, but that was as a role player. Had that never happened, would it diminish the fact he was once a three-time Defensive Player of the Year? That he carried the Orlando Magic to the 2009 NBA Finals?

The year he won the championship, Howard averaged 2.8 points and 2.8 rebounds in 11.8 minutes of game action across six games versus the Miami Heat. Does that magically make him a better player because suddenly there was some hardware at the end of a season where he was 34 and a role player?

Howard didn’t make the NBA 75 list, and he had a better statistical case than Lillard. So maybe none of this matters. Is it better to be beloved forevermore in a city where you didn’t win a title, like Stockton and Malone in Utah, and Lillard in Portland? There’s a certain charm to that.

It links `Lillard to a place more than say, Kevin Garnett, who became a superb player with the Minnesota Timberwolves, but actually got over the hump with the Boston Celtics. Obviously, winning a title with the Trail Blazers would be the ultimate goal, but maybe it is better to be loyal than to have won a ring in a place where you have little affinity, like Howard. Then again, Howard might have a different opinion on that.

It is a fascinating question that we will never truly know the answer to. Fans want titles to validate why the player they love is better than others. True fans and players alike know that there’s a lot more that goes into a career than championships. If Damian Lillard stays in Portland and never wins another playoff series again, his legacy there is secure forever. Hard to put a price on that.