The Whiteboard: What does the perfect supporting cast for Damian Lillard look like?

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This summer, Damian Lillard has repeatedly stated his commitment to winning with the Portland Trail Blazers but the obvious elephant in the room is the roster around him. The past playoff disappointments which have added pressure to the current situation can be traced to myriad factors but with a talent deficit as the most noticeable one. It’s a lingering question for this coming season as well with Larry Nance Jr. and Cody Zeller as the primary offseason additions.

Staring at all that mess, I decided to explore a little thought exercise. How could you build the best hypothetical roster around Lillard using only his Trail Blazers’ teammates, past and present, in their peak seasons with Lillard. Here’s what I made.

What’s the best supporting cast that can be assembled from past and present teammates of Damian Lillard?

Shooting Guard: CJ McCollum, 2016-17 season

McCollum’s 3-point shooting volume is much higher in recent seasons but this year was probably his most all-around dynamic as a creator. He averaged 23.0 points, 3.6 rebounds and 3.6 assists per game, shooting 48.0 percent from the field, 42.1 percent from beyond the arc and 91.2 percent from the free-throw line. He didn’t add a ton as a defender but as a secondary creator and ancillary backcourt scorer, this is as good a complement as there is for Lillard.

Small Forward: Nicolas Batum, 2012-13 season

Nicolas Batum had plenty of productive seasons after this one but in terms of high-level versatility, he probably peaked during Lillard’s rookie season. That year, he averaged 14.3 points, 5.6 rebounds and 4.9 assists per game, shooting 42.3 percent from the field, 37.2 percent on 3-pointers and 84.8 percent from the line. At this point, he was an above-average perimeter defender with positional versatility, a solid outside shooting threat and a strong secondary playmaker with his passing and vision.

Power Forward: LaMarcus Aldridge, 2014-15 season

Aldridge was 29 at this point, but his final season in Portland with Lillard was probably his best fit. It was the first season in which he really took 3-pointers, making 35.2 percent of 1.5 attempts per game — spacing that will be particularly important in a twin-towers arrangement. Aldridge averaged 23.4 points, 10.2 rebounds and 1.7 assists per game this season and it was, overall, one of his most productive and versatile offensive seasons with the Trail Blazers.

Center: Jusuf Nurkic, 2018-19 season

Nurkic has really only had two full seasons in Portland, without significant injury, and 2018-19 was slightly better in terms of both his defensive impact and his offensive synergy with Lillard and McCollum. He averaged 15.6 points, 10.4 rebounds, 3.2 assists, 1.0 steals and 1.9 blocks per game, shooting 50.8 percent from the field and a to-that-point, career-best 77.3 percent from the free-throw line. There is a lot of overlap here with Aldridge in terms of the spaces they would occupy on the floor but he’s the best defensive big man Lillard has ever played with and his value is too high to leave off this hypothetical roster altogether.

Bench: Norman Powell, 2020-21 season

Powell only had 27 games in Portland after getting traded but already proved to be one of the best backcourt partners Lillard has ever had. With the Blazers, Powell averaged 17.0 points, 3.3 rebounds, 1.9 assists and 1.3 steals per game. He only shot 36.1 percent from beyond the arc but brought with him the floor-spacing gravity of a guy who shot better than 40 percent on 3s over his final three-and-a-half season with the Raptors. He’s a dynamic secondary scorer who competes at the defensive end and brings enough creation ability that he and McCollum could function together without a point guard in the handful of minutes Lillard is resting.

Bench: Mason Plumlee, 2016-17 season

It may not be necessary to include another big man in the rotation, especially when Aldridge would likely play some center minutes in the playoffs. But it doesn’t hurt to have another big man who could block shots, defend in space, act as a lob threat and move the ball on offense. Plumlee wasn’t elite in any one area but he checked a lot of boxes, averaging 11.1 points, 8.0 rebounds and 4.0 assists per game during this partial season before he was sent to Denver as part of the Jusuf Nurkic trade. He worked extremely well as an elbow hub for Lillard and McCollum that season and could do the same with bench units on this hypothetical team.

Bench: Robert Covington, 2020-21 season

This was far from the best season of Covington’s career but this group could use another defensive specialist who can handle 3s and 4s and Covington is much better in that regard than other possibilities like Mo Harkless or Al-Farouq Aminu. He averaged just 8.5 points per game last season, the lowest since his rookie season, but Covington added 6.7 rebounds, 1.7 assists, 1.4 steals and 1.2 blocks, shooting 37.9 percent on 3-pointers.

Bench: Wesley Matthews, 2014-15 season

Matthews’ best season with the Trail Blazers was interrupted by an Achilles’ injury after 60 games. But he was off to an incredible start, averaging 15.9 points, 3.7 rebounds, 2.3 assists and 1.3 steals per game, shooting 38.9 percent on a career-high 7.4 3-point attempts per game. He was at his most impactful as a strong, versatile wing defender, spot-up shooter and complementary scorer who could attack smaller players in the post — all attributes that would be key on this roster.

There are a few big takeaways here, the first of which is that even in this hypothetical scenario you might not be able to build a championship contender. This looks like a very, very good roster but I am not sure they would be the favorite in the Western Conference next season, let alone favored over the Brooklyn Nets or defending champion Milwaukee Bucks.

The second is how rarely the peaks of Lillard’s teammates have overlapped. There are really two iterations of Blazers’ teams led by Lillard, the first supported by Aldridge and Batum and the second supported primarily by McCollum. But there are only three pairs of peak seasons here that overlap. The first is Plumlee and McCollum in 2016-17, a season in which Plumlee was traded after 54 games. The second is 2014-15, a season in which Matthews suffered a devastating injury before the playoffs. The last was this past season with Powell and Covington, one of which was acquired at the deadline, and both of whom would be bench players on this hypothetical fantasy roster.

The Blazers have made plenty of mistakes and missteps over the years but they’ve also been hit by bad timing and bad luck over and over again. And even if they had been able to do everything right and avoid some bad breaks, it still might not have ever resulted in a title.