After Winning No. 3 Pick, Should Trail Blazers Pivot From Going All-In Around Damian Lillard?

The Portland Trail Blazers were one of the biggest winners of the 2023 NBA draft lottery. Although they didn’t jump to No. 1, which would have allowed them to select once-in-a-generation prospect Victor Wembanyama, they won the No. 3 overall pick despite having only the fifth-best odds entering the night.

With Damian Lillard set to turn 33 in mid-July and fresh off a career year, the Blazers have made it clear that they have no interest in rebuilding anymore. That means the No. 3 pick could be available to the highest bidder over the next few weeks.

“We’re a team that’s trying to win and trying to maximize Damian’s timeline. This was an important night for us,” Blazers general manager Joe Cronin told Jake Fischer of Yahoo Sports after the lottery. “Front offices around the league think highly of this draft, so you would think that a lot of teams that were sitting [on stage] tonight will be getting a lot of calls from teams trying to move up and maneuver.”

Rival executives expect the Blazers “to explore the kind of veteran help” that they can receive for the No. 3 pick (plus other players), according to ESPN’s Zach Lowe. While their urgency to expedite their rebuild makes sense given Lillard’s age, they’ll need to ensure those short-term gains don’t come at the expense of their long-term future.

After the Blazers’ second straight disappointing season came to an end without a playoff appearance, Lillard declared he had grown tired of rebuilding.

“I don’t have much of an appetite for building, and guys two or three years away from really going after it,” Lillard told reporters in his final press conference of the season. “I want a chance to go for it,” he later added.

Landing the No. 3 pick gives the Blazers a chance to do that. While a megastar like Giannis Antetokounmpo, Joel Embiid or Luka Doncic still might be out of reach for the Blazers, a foundation of that pick, up-and-coming guard Anfernee Simons and veteran center Jusuf Nurkic (for salary filler) could perhaps get them in the door for Toronto Raptors forwards OG Anunoby or Pascal Siakam or Brooklyn Nets wing Mikal Bridges, among others.

To swing a trade for another star, the Blazers might have to first undo one of their previous regime’s mistakes. They owe a protected 2024 first-round pick to the Chicago Bulls that ties up which picks they can trade for the remainder of the decade.

That pick is lottery protected through 2028, at which point the Blazers would instead convey their second-round pick that season. Since the Stepien Rule prevents teams from going back-to-back years without a first-round pick, the Blazers wouldn’t be able to offer a first-rounder in a trade after this year until that pick conveyed to the Bulls.

If the Blazers do lay the framework for a blockbuster trade, they could always try to renegotiate the terms of their deal with the Bulls. If they remove the protections after a certain number of seasons, that would guarantee those picks convey by that point, which would enable them to trade picks in future years again. The Blazers should at least check in on the Bulls’ willingness to do such a deal—and their asking price—but there’s no reason for them to finalize it unless they have a bigger trade in the works.

During his end-of-season press conference, Cronin alluded to having a set of targets in mind, although he couldn’t specifically name names because of the NBA’s tampering rules. However, the Blazers will likely face stiff competition from other teams for any high-profile player on the trade market, which could be a direction-defining decision.

If the Blazers cash in the No. 3 pick and most of their remaining additional assets for the right star, he and Lillard could potentially push them back toward the top of the Western Conference. But if that deal backfires for any reason—look no further than the Minnesota Timberwolves and Rudy Gobert for a recent example—it might condemn Lillard to basketball purgatory for the remainder of his career in Portland.

In an interview with ESPN’s Stephen A. Smith, Lillard made it clear that he’d support the Blazers going all-in.

“I ain’t gonna say I’m putting them on the clock,” he said. “I’m just saying if those things can’t be done — if we can’t do something significant like that [put together a competitive, playoff-ready roster] — then we won’t have a chance to compete on that level. And then, not only will I have a decision to make, but I think the organization will, too. Because at that point, it’s like, ‘Are you gonna go young, or are we gonna get something done?’ I think we just kinda been on the fence with fully committing to either one. I just think we at that point now where everybody wants to win. They believe I deserve that opportunity.”

As tempting as it might be to go all-out for the next star to hit the trade market, the Blazers must be as mindful of the long-term downside as they are the short-term upside. They may deem it worthwhile to pivot fully into win-now mode around Lillard, but they could be increasing their odds of a lengthy rebuild in the post-Lillard era. It all depends on whom they end up targeting and how much it costs to acquire them, but the risk-versus-reward calculus likely won’t be simple either way.

At some point, the Blazers could decide they’d be better off rebuilding and offer to trade Lillard to a contender if he was open to an amiable breakup. He’d immediately become one of the most hotly pursued trade targets in the NBA, so they might be able to name their price to prospective suitors.

A core of the No. 3 pick, Simons, 2022 No. 7 pick Shaedon Sharpe and whatever they got in return for Lillard would be a strong foundation for a rebuild. Then again, the best-case scenario with a package of draft picks and young prospects is finding someone as talented as Damian Lillard, which is hardly a guarantee.

Based on their public messaging, the Blazers appear to have chosen their direction. We’ll find out in a few years whether they grow to regret that decision over time.

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