In this era of player empowerment in the NBA, Damian Lillard’s fierce loyalty to the Portland Trail Blazers is an almost unique relic of a bygone period where superstars stick with just one team throughout their careers.

Lillard has now played 11 seasons with Portland since they picked him sixth overall in the 2012 NBA Draft, putting him in an elite group of only five active players who have played at least 10 seasons with the same franchise that drafted them.

The other four in this quintet are all multiple time NBA All-Stars as well, bannered by the Golden State Warriors’ “Big Three” of Stephen Curry, Klay Thompson, and Draymond Green and capped off with Giannis Antetokounmpo of the Milwaukee Bucks.

While all five members of this rarefied club are bound for the Basketball Hall of Fame upon their eventual retirement, Lillard stands out among these standouts as the only one yet to win an NBA title.

Theoretically, if the Weber State product plays out the upcoming campaign with the Blazers, does not win an NBA title, and decides to retire following the season, he will graduate to another quintet. As a virtual lock for the Hall of Fame, Lillard will eventually join John Stockton, Reggie Miller, Elgin Baylor, and Calvin Murphy on the short list of inductees who played for just one NBA team for a minimum of 12 years and did not win a championship.

It is clear that Lillard’s lack of postseason success is beginning to eat at his legacy and this is shaping up to be the most influential factor for this offseason’s upcoming free agency period. The entire league will be waiting on the decision of Lillard and Portland’s front office on whether or not their partnership is something worth maintaining moving into the future.

The growing consensus among the league’s pundits is that it is likely that Lillard will be on another team come next season, especially in the wake of his comments last month where he cited the Miami Heat and Brooklyn Nets as two teams that he would like to play for.

Furthermore, the Blazers’ selection of Scoot Henderson, who plays the same position as Lillard, with the third overall pick of this year’s NBA Draft gives them a new–and much younger–cornerstone to build around if they do decide to hit the reset button. The team also made it clear following the draft that they intend on holding on to Henderson which further complicates Lillard’s future with the team as the 19-year-old guard was their biggest trading chip.

Miami is a particularly appealing destination for Lillard as the team is coming off its second NBA Finals appearance in four years. The belief is that the Heat’s front office could put together a package centered around 2022 NBA Sixth Man of the Year Tyler Herro and a slew of draft picks to acquire Lillard who would then join Jimmy Butler and Bam Adebayo to form a fearsome trio that should once again compete for an NBA Finals berth.

This gamble makes sense for Miami as a win-now move with not much downside. The 32-year-old guard’s contract runs for at least the next three seasons and has a $63 million player option that he is likely to exercise for ‘26-’27. Though Lillard is slowly moving into his mid-30s, his ability to knock down three-pointers at a historic level will allow him to age gracefully.

No other team has a situation that is as enticing as that of the Heat, albeit the news cycle over the past few days has made it known that Lillard and Portland may not yet be ready to call it quits. The team believes that a backcourt with both Lillard and Henderson can not only work, but also compete for a championship.

While the optimism of the Blazers’ front office is nice, there is sizable evidence that pairing Lillard with an undersized scorer will not pan out. For six and a half seasons, Lillard partnered with the 6’3 CJ McCollum in a high-scoring backcourt that was moderately successful. After they traded McCollum away in the middle of the ‘21-’22 campaign, they then doubled down on their strategy and replaced him in their starting line-up with another shoot-first guard in Anfernee Simons.

Over these eight seasons from ‘15-’16 to ‘22-’23 where Lillard started alongside either McCollum or Simons, Portland managed to break the 50-win barrier only once, which was in ‘18-’19. During this season, they made a run to the Western Conference Finals that is now looking more like an aberration than anything else.

Curiously, in the two seasons prior to McCollum’s promotion to the Blazers’ first five, the team won 54 and 51 games, respectively, in Lillard’s second and third campaigns in the NBA. During this period, Lillard lined up with the defensive-minded Wesley Matthews who could take on the assignment of covering the opposing team’s best perimeter scorer while spacing the floor with his three-point shooting as well.

Aside from the talks about the potential Lillard-Henderson backcourt duo, the Blazers have also been involved in trade rumors over the past week. Green, Adebayo, and DeMar DeRozan have all been floated as candidates to join Lillard in the Rose City.

The thesis of teaming up Lillard with more defense-oriented players like Green and Adebayo is a sound, if not excellent, one and the passing ability of these two players is an added bonus that allows for immense upside.

Green is an unrestricted free agent this offseason and could realistically join the Blazers, though it will have to be through a sign-and-trade given the team’s salary cap situation. However, it remains to be seen if the 2017 NBA Defensive Player of the Year Green will be willing to leave the Warriors with whom he has won four NBA titles with and are the only team that he has ever played for.

The situation with Adebayo, on the other hand, is more of a fantasy at this moment. It is unlikely that Miami will part with their 25-year-old center who is already a two-time NBA All-Star and four-time NBA Defensive Team member. It will take a massive haul for the Heat’s front office to even consider a trade involving Adebayo and Portland’s rumored packages centered on Simons and Jusuf Nurkic are not even remotely alluring.

Meanwhile, Lillard and DeRozan together will form what could be the league’s highest scoring duo. In a vacuum, this has the potential to be a successful match. The Blazers’ front office will have to surround them with a top notch defensive group if they are to be successful though given that neither of these two talented scorers is more than an average defender.

Unfortunately, the track record of Portland’s executives for most of this decade, as demonstrated by the team’s performance, is quite uninspiring and it is improbable that they can pull off enough moves to maximize this prospective Lillard-DeRozan pairing.

With all this said, it looks like the best move for Lillard and the Blazers moving forward is to go their separate ways. If his priority is truly winning a championship, Lillard’s best shot at this is and has always been elsewhere given the commitment to mediocrity shown by the moves of Portland’s front office since his arrival.

Lillard’s ability to shoot should help him fit in almost anywhere and adding him to any borderline contender will immediately boost their chances.

For the Blazers, resetting their timeline to that of Henderson will relieve them of the pressure that has come with the desire to construct a team that can compete for a title. They can now focus on making decisions for the long run instead of zeroing in on win-now moves.

This union has run its course and it has become more obvious than ever that it is time for Lillard and Portland to go on their own way.