Damian Lillard has openly and repeatedly expressed a desire to contend, yet, the Portland Trail Blazers continue to stockpile budding young talent and even obtained the third overall pick in the 2023 NBA Draft after some unexpected lottery luck. This creates conflicting directions within the Blazers franchise, one that has consistently tried to build a contender around Lillard, only to fall short time and time again while failing to make the playoffs the past two seasons. Before deciding to tank during those two seasons, the Blazers were an average team at best, so now comes a pivotal crossroad: trade the third overall pick along with their young players to pair Lillard with a second star or go all in on a rebuild and construct the team around their third overall pick? There’s plenty to watch with the Blazers during the 2023 NBA Draft, as they could either draft their future cornerstone or possibly trade for a second superstar.

What Happens with the Third Pick?

The Charlotte Hornets are all but guaranteed to select either Brandon Miller or Scoot Henderson with the second overall pick, as presumed first overall pick Victor Wembanyama will head to the San Antonio Spurs. This leaves the Trail Blazers in a tricky situation. The Hornets already have their franchise player and all-star point guard in LaMelo Ball, so even though Henderson might be the best available at number two, Miller will likely fit better next to Ball, given that he’s a score-first wing who can play off the ball. Henderson is a ball-dominant point guard, and since the Hornets already have a ball-dominant point guard in Ball, most assume the Hornets will draft Miller instead. Like the Hornets, the Blazers are in a similar predicament: they already have superstar point guard Damian Lillard and a rising young point guard in Anfernee Simons. If the Blazers want to keep the third overall pick instead of trade it, what the Hornets do at number two is crucial to Portland’s future. I don’t see the Blazers selecting Henderson third if they already have Damian Lillard, Anfernee Simons, and Shaedon Sharpe, the seventh overall pick in the 2022 draft that took over much of the ball-handling duties late in the 2023 season. Two other possibilities with the Blazers’ third overall pick might include drafting someone not named Scoot Henderson or Brandon Miller (the Thompson twins are very intriguing players) or trading the pick before the draft to solidify a clear direction of championship contention.

Build Around Lillard?

Even though the Blazers are oozing with some great young talent in Anfernee Simons and Shaedon Sharpe, they’ve quietly put together a perfect trade package to acquire any available superstar. The keyword here is available: which superstars are actually on the trade block? There’s none that we know of currently, but there’s been speculation about Bradley Beal and Jaylen Brown. Regardless, the Blazers could package Simons, Sharpe, their longtime center Jusuf Nurkic, and the third overall pick (there are many other draft picks they could include too) to acquire a superstar to pair with Lillard. The issue is the Blazers are reportedly unwilling to include Sharpe in any trade packages with the third overall pick, per Jake Fischer, which could severely hurt their chances of trading for a star because Sharpe has one of the highest ceilings of any young player in the NBA today. Still, it’s likely that Simons, Nurkic, the third overall pick, and their other 2023 draft picks and future picks can get them an all-star caliber player to pair with Lillard. I included some mock superstar trades below this section to demonstrate what these moves might look like. The Blazers did a similar thing last offseason with Jerami Grant, whom they only had to trade one first-round pick to acquire, so it’s possible they will execute something similar this year. The Blazers have also done an extremely clever job of creating cap space, so even if they trade for another star, they’ll still have the flexibility to keep Grant (a free agent this summer) if he wants to stay.

Key Free Agent Decisions

Jerami Grant is the most important free agent this offseason for the Portland Trail Blazers. He averaged over 20 points per game (PPG) on more than 40 percent from the three-point line with good defense. Those types of players are hard to find, and he was a perfect fit next to Lillard before the Blazers shut them both down for the season. The Blazers could replace him through a trade, but since that’s not a guarantee, resigning Grant is pivotal to Portland’s chances of returning to the playoffs. According to Spotrac, Grant’s salary was $20.9 million for the 2023 season, and given his scoring prowess, elite shooting, and stellar defense, he’ll likely command somewhere north of $30 million in free agency. The Blazers can offer him the most money because they have his bird rights, but Grant may want to sign somewhere else where championship contention is more certain. In addition to Grant, Cam Reddish and Matisse Thybulle were some key trade acquisitions during the 2023 season, and they are up for new contracts this summer. They are restricted free agents, and the Blazers have their bird rights. Reddish and Thybulle performed well as solid shooters and defenders at the wing positions, but they didn’t necessarily contribute to winning after the trade deadline. Reddish and Thybulle would be good to keep because of their length and size defensively, but they wouldn’t help as much in taking the offensive responsibilities off Lillard. The Blazers might let them both walk to resign Grant or make a blockbuster trade, but Reddish and Thybulle should improve a Blazers’ defense that has ranked near last in the NBA for the past few years. Other notable free agents include backup center Drew Eubanks and forwards Kevin Knox and Justice Winslow. Eubanks played well in spurts, Knox showed some scoring growth, and Winslow was an excellent glue guy at the beginning of the season, but their futures in Portland are unclear. All things considered, resigning Grant should be the Blazers’ top free agency priority. Resigning Reddish or Thybulle might be nice too, but all of these major decisions will contend with what the Blazers do during the 2023 NBA Draft.

The Talented Young Core

If the Blazers wanted to go all-in toward a rebuild, they have a young, dynamic duo to build around in Anfernee Simons and Shaedon Sharpe. They’re super young and athletic with versatile scoring packages. The problem is if the Blazers want to build around Lillard instead of Simons and Sharpe, those guys are perfect to include in any blockbuster trade. While it’s unclear what the Blazers will do with the third overall pick, Simons and Sharpe have already created one of the NBA’s most intriguing young cores, and it’d be a major risk to trade them away. Simons broke out during the 2023 season and averaged over 20 PPG on nearly 38 percent from three, while Sharpe averaged over 23 points and five assists during the last five games of the season (all against playoff teams). Simons, Sharpe, and the third overall pick will create an extremely talented young core to rebuild around, but the more Lillard expresses his opposition to a rebuild, the more uncertain it becomes for the future of Simons and Sharpe in Portland.  

What’s Next?

After analyzing the Blazers’ current situation, I believe that they will not trade the third overall pick, regardless of the Hornets’ decision. The Blazers could still draft Henderson or Miller and package them in a later trade to acquire another all-star. I also believe they will try to resign Jerami Grant and possibly either Matisse Thybulle or Cam Reddish. Luckily, the Blazers have the young assets and cap space to go in whatever direction they want this summer. Their front office has done an excellent job of positioning themselves to acquire a superstar but also pivot to a rebuild if necessary. The Portland Trail Blazers are the team to watch in the 2023 NBA Draft, and the excitement surrounding their offseason moves will only increase as the draft draws near.