The Complicated Future Of Damian Lillard & The Blazers

It’s no secret that the Portland Trail Blazers have had a disappointing season, especially on the heels of an offseason where the franchise re-dedicated themselves to superstar Damian Lillard.

The Blazers went out and acquired Jerami Grant, and added lottery pick Shaedon Sharpe to the fold, only for the Blazers to find themselves outside the play-in picture, and with Lillard nearing a season-ending shutdown.

So, what’s next for the Blazers? One would think the play is to run it back next year and try again, because that’s been their pattern during the Lillard era, after all.

Perhaps, then, it’s time for change. Specifically, it might be time for the Blazers and Lillard to have an uncomfortable conversation about where their marriage is heading.

The conclusion, ultimately, should be a divorce between the All-Star point guard, and the franchise who drafted him 11 years ago.

But first, let’s acknowledge that Lillard inarguably has been the best Blazer to ever wear the uniform. Trading him would be a monumental decision that fans of the franchise will feel for years.

And while some might be tempted to point a finger in Lillard’s direction for the Blazers never making a Finals run during his tenure, that would be unfair. It was always the Blazers’ mission to build a competitive team around him, but that somehow never materialized. They occasionally fielded good teams that would surprise in the postseason, but not a single time did management succeed in providing Lillard with the necessary weapons to make them a legitimate championship contender.

Now, at age 32, Lillard is in a rush. He’s played the best brand of basketball of his career this season, netting 32.2 points and 7.3 assists per game. He remains one of the most dangerous offensive players in the history of the point guard position, but the question is: For how much longer?

Lillard has coming up on 28,000 career minutes spread out across 769 games. It’s fair to wonder if the downward trajectory will soon commence, in which case Lillard would need to be surrounded by much more potent weapons than he currently is.

Parting ways would also give the Blazers an opportunity to try again, this time from scratch. Lillard would fetch an enormous haul, allowing the Blazers the opportunity to build around Sharpe and Anfernee Simons, by building through the draft.

Add in follow-up trades of Grant and Jusuf Nurkić, and the Blazers could find themselves in a highly exciting youth movement, where they might get the right formula this time.

The alternative, of standing pat, seems the most skeptical route. Lillard of course holds all the cards. If he’s determined to finish his career with the Blazers, Portland would have a nightmare on their hands if they traded him against his wish, as that would sully the last 11 seasons, and likely create animosity between Lillard and the franchise, with the fan base stuck in the middle.

Of course, the Blazers could for one last big swing, using Sharpe and Simons as major pieces in a potential superstar trade, should one become available. They’re already considering avenues to get out of their draft pick obligations with Chicago, just to open up more trade flexibility long-term.

Would Lillard and Player X be enough for the Blazers to finally catapult themselves into proper contention? That heavily depends on who Player X is, and given that the superstar market seems to be getting more expensive by the day, it’s fair to wonder what Sharpe, Simons, and future firsts fetches them. If the best player available for such a package is, say, Karl-Anthony Towns, is that worth it?

The best possible piece, particularly to pair with Lillard, went off the chessboard during the trade deadline when Kevin Durant got shipped off to the Phoenix Suns. It’s unlikely that a player of his caliber suddenly is available.

This is all to say the Blazers have two options.

They can go all-in on a rebuild, where they dictacte terms, and spend half a decade building themselves back up.

Or, they can relinquish their final young trade pieces, and see if the return is enough to open up a slim title window.

The latter seems far more unlikely, especially if the best player they can get isn’t enough to get them out of the second round, making that avenue potentially worthless. The stars would have to align just right for the franchise to find an elite talent available in trade before the start of next season, and for them to be able to field an offer that beats out, say, the Oklahoma City Thunder and their treasure chest of future draft picks.

As for Lillard, it might be time to figure out what he wants for the future. There’s no problem wanting to remain a Blazer for the rest of his career, as long as he understands that likely comes with a heavy dose of mediocrity. If he’s all right with that fate, and the Blazers are too, that’s perfectly reasonable.

They’d become a team, however, no one would need to worry much about for a handful of years. But perhaps that’s simply the price of loyalty these day.

Unless noted otherwise, all stats via NBA.com, PBPStats, Cleaning the Glass or Basketball-Reference. All salary information via Spotrac. All odds courtesy of FanDuel Sportsbook.