Should Trail Blazers trade Damian Lillard, build around Scoot Henderson?

Damian Lillard and the Portland Trail Blazers are trying to reshape themselves into a contender, with the latter viewing the addition of Scoot Henderson, the No. 3 pick in the 2023 NBA Draft, as a substantial enhancement. But is the prudent direction for Portland to trade Lillard and rebuild with Henderson, instead of retooling around Lillard?

On Friday’s edition of the “The Herd,” host Colin Cowherd argued that Portland’s roster construction is too wing-heavy, and it’s time to move on from Lillard.

“Four of the most talented Blazers are guards: Scoot Henderson, maybe the most talented, Dame, Anfernee Simons and Shaedon Sharpe, and they have one solid wing [if he’s re-signed], Jerami Grant. They’re essentially now becoming the Warriors without any of the trophies,” Cowherd said.

“Steph and Klay, I understand the loyalty to Klay. You got the bag four times; you got the rings. The Blazers had Dame and CJ McCollum, and they didn’t get you trophies. They got you admiration, people liked them … Eleven years, four series wins. Break ’em up. They never did … Too many guards, what are you gonna get for it? Break ’em up. Send one packing. Scoot Henderson is the future.”

Lillard is coming off the most productive season of his NBA career. He averaged a career-high 32.2 points and 7.3 assists per game while shooting 46.3/37.1/91.4. Lillard had a 60-point game against the Utah Jazz and a 71-point game against the Houston Rockets. 

Across his 11-year NBA career, Lillard has racked up seven All-NBA honors and seven All-Star Game roster nods. He will be 33 by the 2023-24 NBA season and is under contract through the 2026-27 season.

The Trail Blazers went 33-49 last season, good for 13th in the Western Conference. They missed the playoffs for a second consecutive season and haven’t won a playoff series since 2019. Since Lillard’s rookie season (2012-13), Portland has won just four playoff series.

Henderson is coming off an impressive season with the NBA G League Ignite. The 6-foot-2 Henderson averaged 16.5 points, 6.8 assists, 5.3 rebounds and 1.1 steals per game while shooting 42.9/27.5/76.4 across 19 games. He’s the highest draft selection made by the Trail Blazers since 2007, when they selected Ohio State big man Greg Oden with the No. 1 pick.

The Trail Blazers also selected Iowa forward Kris Murray — who earned All-Big Ten first team honors last season — at No. 23 and wing Rayan Rupert at No. 43 in the 2023 draft.

Concerning the rest of Portland’s roster, Simons averaged a career-high 21.1 points per game last season. Sharpe — a former five-star prospect who the Trail Blazers selected with the No. 7 pick in the 2022 NBA Draft — averaged 9.9 points per game and appeared in 80 contests (15 starts) in his rookie season.

Of all of Portland’s young talent, Cowherd sees Henderson as Portland’s future.

“Dame’s a great player, but after about four practices of Scoot, his youth, he’ll be able to play 75 games, he’ll be a willing defender, you’re gonna look around and go ‘we gotta get Scoot some players,’” Cowherd said. “And Scoot’s not gonna win a title next year, but at least it’s a solid direction and everybody gets it. Keeping these guys together, what are your paths? You got two paths. I don’t think either one of them gets you close to a title. I think both of them get you maybe at best into the bottom of the playoffs.

“All these guards in the bigger West, make a move. Your future is clearly Scoot Henderson. Nobody disputes that. Your near future could be Dame. How about just moving him [Lillard] and getting pieces around Scoot? 

“Rebooting, 11 years, four playoff wins. It’s not that emotionally hard. It would be different if you had rings and trophies. You never really got close.”