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Can Damian Lillard and Scoot Henderson Really Play Together?

Portland wants their star guards to co-exist. How realistic is that expectation?

NBA: Portland Trail Blazers at Atlanta Hawks Dale Zanine-USA TODAY Sports

Ever since the Portland Trail Blazers drafted point guard Scoot Henderson third in the 2023 NBA Draft, Portland’s fan base has been a hotbed of excitement and barely-suppressed trepidation. On the one hand, the Blazers got one of the best players in the draft, a talent deemed by some to be franchise-changing. On the other, Portland already has a franchise-changing point guard in Damian Lillard. What, exactly, are they trying to accomplish by drafting another?

At least publicly, Blazers General Manager Joe Cronin has bridged that canyon by walking with one foot on each tightrope. He’s been ebullient about Henderson’s potential, affirming that the Blazers will keep the rookie in the fold. He’s also reaffirmed his pre-draft vow to build around Lillard.

Despite the assurances from on high, fans still have plenty of questions about that least if the Blazer’s Edge Mailbag is any indication. Here’s one that tackles the issue head-on.


I need you to level with us. Can Dame and Scoot really play together? What are the strengths and weaknesses and what needs to happen to make it work, if it even can? Every morning I find myself doubting it’ll work but by evening I talk myself into it. This is going to have me up at night if it doesn’t get resolved. Help!


Strengths are easy. They’ll be two of the best guards in the NBA. With his athleticism and dedication to the game, Henderson should evolve into a better defender than any of Dame’s backcourt mates since Wesley Matthews. Scoring shouldn’t be a problem either. You can never have too much talent. Drafting Henderson will not only fulfill that maxim in Portland, but stretch it to its limits.

The list of weaknesses is shorter, but each item weighs heavily enough to blunt the promise of the last paragraph, or at least bend it.

Both Henderson and Lillard are 6’2. Height listings are sometimes sketchy, but theoretically, he’s shorter than CJ McCollum or Anfernee Simons. No matter how good of a defender Scoot ends up being, that’s going to cause issues when pairing the two stars. Somebody is going to have to defend off-guards. For given play, that’s fine. 32 minutes a night over 82 games, other teams are going to exploit that mismatch.

Lillard is already taxed guarding opposing point guards. If he draws the shooting guard assignment, he’s not going to prosper. But playing the rookie out of position isn’t a recipe for success either.

Offense will be interesting as well. Both players thrive with the ball in their hands. They’re not both going to get it. Nor do they have a ton of flexibility in managing that situation. Henderson doesn’t have a reliable long-range shot yet. He’s going to want to bull past defenders for the pull-up, layup, or foul shots. Meanwhile the primary off-ball scoring threat—the catch-and-shoot three—isn’t in his arsenal yet. That pretty much mandates Scoot having the ball.

This puts Lillard in the interesting (awkward?) position of being the superstar veteran, an All-NBA player, a 30-point scorer, ceding the team to an untested rookie. In everything but putting his head down and driving the lane, Lillard will be superior to Henderson at first. For the sake of developing the young star and giving his team a chance, Lillard will have to absorb the lost plays—and maybe games—that come with them.

Dame has shown willingness to share the court, and ball-handling duties, with teammates before. He did it with McCollum and Simons. But this will turn the volume up to 11. Henderson is more heralded, and less experienced, than either. Henderson’s shooting is considerably worse too. “Sharing” will need to turn into “giving over” until Scoot finds his range.

This creates a weird dynamic for the rookie. A third-overall pick is normally given carte blanche to develop. He’s the savior, the superstar-in-waiting. Teammates, coaches, the front office, and fans are more than willing to live with growing pains, knowing there’s a clear direction forward and one set of shoulders that direction is pinned to.

Looking over those shoulders is not normally a part of the process. With Lillard in the backcourt (and winning with him the ultimate agenda), that would become the norm. Unless carefully managed, every mistake, every steep area of the growth curve, would be accompanied by shakes of the head and muttering that Dame could have done it better.

If you think Backup Quarterback Syndrome is bad, wait until your backup quarterback is a seven-time All-Star, the most accomplished and popular player in franchise history.

Getting back to Lillard...even if he were willing to do all this—and I believe he would be, in theory—to what end, from his point of view? He already made concessions to accommodate McCollum and Simons. Twice now Dame has shaped his game—joyously and willingly—around prominent, yet somewhat duplicative, guards. The end result was extended mediocrity.

Sacrifice must be accompanied by purpose. Absent that, it becomes meaningless.

In this situation, Lillard has every right to tilt his head and say, “’re telling me after all these years of trying the same experiment that this time it’ll finally work? With a rookie who’s not just accompanying me, but literally encroaching on my position? Fool me once, shame on me. Fool me twice, shame on me. Fool me three times? Thanks, but I gave at the office.”

One could rightly argue that Henderson has more potential than either McCollum or Simons. Both guards became offensive powerhouses, high scorers and accurate shooters. Scoot might have a high ceiling and a different skill set, but how much better (and/or more productive) could he really be? He’s going to make THAT much difference?

Lillard also has the final trump card in that conversation. By the time we find out for sure, he’ll be pushing 40. Even if Scoot were to be all-universe, Dame might not last long enough in the league to experience it meaningfully.

Can Lillard and Henderson play together? It all depends on what Dame is willing to do, to what extent, and for how long. Whether he can, or should, make the sacrifices necessary to make it happen is an open question. A better one might be whether he should be asked to do so in the first place.

I believe the pairing between the two guards could work out and will, at least for the short term. Whether it’ll be the best solution for either of them remains up to debate.

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