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The Battle Between Loyalty and Legacy: Damian Lillard and the Perils of Ring Culture in the NBA

As the future of the Blazer point guard remains unknown, the conversation over his loyalty to the franchise that has drafted him has morphed into platitudes about legacy

Being a superstar player in the NBA is an interesting exercise in mental gymnastics. First and foremost there is a lot of pressure. Pressure from the city you play in and the fans that buy your jersey, from analysts that expect you to be the next big thing, and from your hometown to make them proud. When you are drafted into a new city, you will often become an integral part of the community, where you will do some work to win the people over. And the city will love you…until they don’t. Whether it is by demanding a trade in your prime to a more desirable location or staying with the team that drafted you and being perceived as holding them back.

Portland Trail Blazers point guard Damian Lillard is a prime example of a superstar that has stayed with the team that drafted him well into his prime. If you asked the average NBA fan to associate one word with Lillard, there is a good chance that word would be “loyalty’. Dame has been adamant that he wants to win in Portland, and for much of his career, he has been praised. But in recent years many have started to look at this same dedication to the Blazers as something that is holding him back. Taking a step back and looking at the perception of Dame is a front row seat to the neverending battle between a players legacy and a sense of commitment to a city and fanbase.

The Aftermath of the New Standard

For many years, it was normal for a star player to be drafted to a team and spend the bulk of their prime with that team. In the past, we have seen players that don’t win a title stay with their teams for the bulk of their careers. And when they finally move on to a different team they are a shell of what they used to be. We saw this with Allen Iverson, Patrick Ewing, and John Stockton among others; players that committed over a decade to a single organization only to fall short of claiming the sport's ultimate prize.

This precedent all changed when LeBron James signed with the Miami Heat after 7 seasons in Cleveland that had many playoff runs but no championships. With the now infamous “Decision”, James helped to usher in a new movement of player empowerment. Where players choose their destiny, team up with their friends and form teams that are built to win championships. We have seen this trend increase in recent years, and the result has been players asking out of their deals for better situations with teams in preferred destinations.

It has become expected now that after a big extension, a team with a star player is on the clock. They need to make as many moves as possible to ensure their young superstar remains content. Whether it be adding another star piece or surrounding the team with effective role players, the standard now is that to prevent a trade demand that the team needs to get aggressive. With Damian Lillard, the after effects of this new standard has been many summers of speculation that he will ask out of Portland, a team that has now missed the playoffs the last two seasons and has only been out of the first round twice since 2016.

But yet, Dame has remained adamant. Convinced that the Blazers can turn it around and help him contend for the success that has eluded him in his career. Lillard has been very vocal about not wanting to be a part of a rebuild, but all indications are that he is happy in Portland and would like to stay there. For many years, NBA fans praised Lillard’s loyalty, remarking how he was the antithesis of the player movement era. But praise doesn’t last forever, as many have grown tired of Lillard’s platitudes about being loyal to the franchise that drafted him. We are currently witnessing a narrative shift in real-time from admiration of athlete loyalty to concerns over the legacy of one of the greatest shooters we have ever seen.

Legacies and Ring Culture

At the highest level of basketball debates on cable television, many hours have been spent arguing on the greatness of LeBron James versus Michael Jordan. This is a debate that I retired from years ago, as it is impossible to compare two different eras. Both players have a legitimate contention for being greater than the other. A LeBron fan could argue for his records and longevity, while Jordan fans can argue that Jordan’s peak was more dominant than anyone else’s peak. But an argument that always comes up in this debate is the 6 for 6 logic, that Michael Jordan went to 6 NBA Finals and won all 6 whereas LeBron went to 10 and only won 4. This argument is the definition of NBA ring culture.

Ring culture tends to ignore any nuance that we see in the game, and defines a player's greatness in leading teams to championships in their prime. It’s why Bill Russell by many historians is more revered than Wilt Chamberlain, despite Chamberlain being the more gifted player. It’s why Olajuwon is more revered than Patrick Ewing, and it is why Chris Paul and Russell Westbrook are often viewed as a notch below other point guards historically. Ring culture defines so much of what we see as basketball fans, that we become blind to great players that just weren’t fortunate enough to win an NBA championship.

While NBA fans like Damian Lillard, the small voices of concern about his legacy having never made it to an NBA Finals let alone won one has gotten louder in recent years. Lillard’s accolades outside of that are impressive. He is a 7-time All-Star, Rookie of the Year, 7-time All-NBA selection, a member of the NBA’s 75th Anniversary Team, and has averaged over 25 points per game in 7 of his ten seasons in the league. In terms of the record books for the Blazers, Lillard is first in 3-pointers made, free throws made, points scored, points per game, and free throw percentage. He is also second all-time for the Blazers in assists (behind Terry Porter) and field goals made (behind Clyde Drexler). All of that alone, cements Lillard as the greatest Blazer player since Clyde Drexler and perhaps since Bill Walton. At worst, he is the Blazers third best player in franchise history.

But that is not enough for NBA fans, it is about the rings. So instead of lauding what Lillard has accomplished we instead lament that he hasn’t hoisted the Larry O’Brien trophy. We have spent off-seasons wondering if the Blazers will trade him to the Lakers, Knicks, Heat, or Celtics. We do this because we have been taught to define NBA success by the standards set forth by Michael Jordan, LeBron James, and Kobe Bryant. And as a result we have turned admiration for Lillard’s commitment to the Blazers as a weakness of a player digging his heels into a stubborn stance.

Looking Ahead

Damian Lillard has made it clear that he wants to win, and that he craves success more than anything. He would also prefer to do that in Portland, but if the team wants to rebuild then he will need to move on. The team used all three of their draft picks this week to draft young prospects Scoot Henderson, Kris Murray, and Rayan Rupert. Henderson seems like a transcendent guard that would have been a #1 overall pick if Victor Wenbanyama didn’t exist. Murray, the brother of Sacramento Kings player Keegan Murray, looks like he can form into a reliable wing shooter at the next level. The issue for Portland is centered around who is already on the roster.

The team has two volume scorers in the backcourt with Lillard and Anfernee Simons, and they now add another in Scoot Henderson. The team also has a dynamic young wing player in Shaedon Sharpe who they are viewing as a building block of the future. In the immediate future, it seems that the Blazers will need to trade one of Simons or Lillard to make way for Henderson. In order to stay competitive with Lillard, it is reasonable to assume that the Blazers would trade Simons and some other pieces to acquire an All-Star caliber player to pair with Lillard, while developing Henderson as the team competes at a high level.

This is not a foreign concept, the Warriors have been trying to accomplish this with the development of Jonathan Kuminga while they still play winning basketball with Steph Curry. Additionally, the Knicks have done this with the development of RJ Barrett around the two-headed duo of Jalen Brunson and Julius Randle. It is possible, but the question becomes if the Blazers want to go down that path and if Lillard will want to see it through with them. The allure of being paired with Bam Adebayo in Miami or with Joel Embiid in Philadelphia is incredibly enticing.

Ultimately, because of the landscape that we are currently in it seems that a Damian Lillard trade is inevitable. Where that trade happens is still unclear. But the true takeaway for me from all of this back and forth about Dame and his loyalty is that in the context of the larger NBA viewership, loyalty is a great thing. But it will never outweigh the 800-pound gorilla in the room that is ring culture. And while we are having these conversations, we have forgotten what Dame has accomplished and instead only focused on what he hasn’t, which says more about the way the collective NBA monolith views than it does about Damian Lillard the basketball player.

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