Are Damian Lillard and Portland Trail Blazers the ultimate tragedy of today's NBA?

Portland Trail Blazers superstar point guard Damian Lillard is coming off a historic performance of 71 points and 13 3-pointers against Houston on Sunday (Feb. 26).

The game marked the highlight of what has been the best season of the 32-year-old’s 11-year career so far. Lillard is averaging a career-high 32.3 points, 4.3 rebounds, 7.2 assists, 0.8 steals and 4.3 3-pointers per game while shooting 47.2% and 38.1% from the three.

Nevertheless, Portland is outside the play-in picture (29-31, 11th in the West), while Lillard isn’t even in the MVP discussion. That begs the question: are the Blazers wasting the best year of prime Damian Lillard, and is Portland stuck in no man’s land?

Looking at the Blazers’ current roster, they have a mix of young talent and above-average veteran players but no true co-star. They also severely lack bench depth and defense. Portland’s second-leading scorer this season has been 23-year-old shooting guard Anfernee Simons (21.4 ppg). Meanwhile, the Blazers rank dead last in the NBA in bench scoring (25.7 ppg) and 27th in defensive rating (116.7). This is surely not a recipe for a title contender.

Going back to previous years, the Blazers have been in similar situations time after time. They often add veteran role players around Lillard who complement him and make moves for solid players good enough to be third options, but they never make a big splash.

In fact, the team’s biggest deal involved trading away Lillard’s former co-star CJ McCollum to New Orleans last season in a cost-cutting move. That probably lowered Portland's ceiling, but even still McCollum is a zero-time All-Star.

Since Damian Lillard was drafted No. 6 by Portland in 2012, his highest-scoring teammate has been LaMarcus Aldridge (22.5 ppg). Aldridge last played for Portland in the 2014-15 NBA season. Aldridge is followed by Jerami Grant, who's averaging 20.6 ppg in his first year with the Blazers this season. McCollum is third, averaging 19.0 ppg during his nine seasons in Portland. So simply put, Lillard has not had enough help.

That's a big reason why the Blazers have finished outside the top four in the West in seven of the last ten years. They have also never finished higher than a third seed with Lillard. Despite having a 419-339 all-time regular season record with Lillard, the Blazers’ playoff record is well below .500. Portland has gone just 22-39 in the playoffs and won just four total playoff series with him.

Portland is now once again left paying their beloved superstar a max contract ($42.5 million this season) to carry a mediocre team on his back. Meanwhile, the Blazers’ ceiling is looking like a first-round exit.

It’s certainly a tragedy, and probably the biggest one in the NBA, given Damian Lillard’s consistent loyalty to Portland. However, it’s difficult to argue that the Blazers are much more than a middle-of-the-pack treadmill team, going by their current roster construction.

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Can Portland Trail Blazers still salvage rest of Damian Lillard’s career?

Portland Trail Blazers superstar point guard Damian Lillard

As for what the Portland Trail Blazers can do to salvage the rest of Damian Lillard’s career, it would likely involve mortgaging their future.

Portland still has all of their first-round draft picks from 2024 to 2029. Their 2023 first-round pick is also lottery-protected, so they will keep it if they miss the playoffs this season. The protections on the pick will carry over each season until 2028. In addition, the Blazers are owed New York’s 2023 lottery-protected first-round pick.

So overall, Portland has a decent amount of draft capital. The team also has desirable young prospects like Anfernee Simons and Shaedon Sharpe. So if the Blazers want to, they could still make a move to go all-in on winning now with Lillard.

There has been constant turnover among star players in the last decade, with countless stars requesting trades. The Blazers could position themselves to be next in line for the next disgruntled star like Bradley Beal, Karl-Anthony Towns or Zach LaVine.

The problem, as previously mentioned, is that Lillard is already 32. So there’s no telling how many prime years he has left. If Portland really wanted to make a blockbuster trade, it would have made more sense to do so when Lillard was in his late 20s. If the team trades all their future assets now, they risk Lillard declining, which could be a disaster.

So all things considered, it looks like Portland may have missed their window to go all in on winning a title with Damian Lillard. So as tough as it is, the Blazers’ best bet may be to just trade Lillard to a contender. In doing so, they would receive a massive haul, while Lillard would finally get the opportunity to add a title to his legendary resume.