How the Portland Trail Blazers can win the Damian Lillard trade

More than five months after the deal went down, it appears the winners of the Damian Lillard trade are...the Boston Celtics. The C's acquired Jrue Holiday, who went from Milwaukee to Portland in exchange for Lillard, just days after the original blockbuster in what should be considered Part II of the Lillard trade. As of March 5, the Celtics have the best record in the NBA and it's not even close.

Lillard hasn't completely found his footing yet in Milwaukee. His scoring numbers and shooting percentages are the lowest they've been in a full season since 2014-15. The Bucks are a championship-or-bust team, though, and should enter the playoffs as a top-3 seed in the Eastern Conference, giving Dame his best shot at a title yet.

The deal hasn't been a disaster for the Blazers, but it hasn't been great, either. Robert Williams III, acquired as part of the Holiday trade return, had season-ending knee surgery after six games. Malcolm Brogdon has been a helpful veteran who's played well when healthy.

Toumani Camara has solidified himself as a role player in Portland after arriving from Phoenix. The Blazers also acquired Deandre Ayton from the Suns as part of the deal, but he's been underwhelming so far despite a recent uptick in production before hurting his hand.

But Portland certainly isn't "winning" the Lillard trade - although it doesn't have to end that way. Here are two paths to the Trail Blazers ultimately conquering a deal that sent away the most beloved player in franchise history.

1. Scoot Henderson or Shaedon Sharpe becomes a superstar

If Portland is ever going to be considered the winner of a trade like this, it'll need to find a superstar. Like a Jayson Tatum-, Devin Booker-, Shai Gilgeous-Alexander-level superstar. It's nearly impossible to win a championship without that caliber of a player. And no one on the current roster other than Scoot Henderson or Shaedon Sharpe has that kind of upside.

Anfernee Simons, if he stays healthy and continues to develop his game outside of scoring, may come closest. But Simons is already in his sixth NBA season. Despite being only 24 years old and improving across the board this year, Ant will likely never become Tatum, Booker or even Tyrese Haliburton.

Can Scoot or Sharpe reach that level? It remains to be seen, but there's no reason to put a ceiling on either of them yet.

Henderson has had a rough rookie season. In retrospect, the league (and Portland GM Joe Cronin) overhyped Scoot as someone who could rival Victor Wembanyama for Rookie of the Year. Realistically, he was a 19-year-old beginning his career on a bad team playing the game's most difficult position.

There's still a long way to go for Scoot, but he's gotten better as the season's progressed. In his first 20 NBA games, Henderson averaged 11.1 points, 2.6 rebounds, 4.5 assists and 3.0 turnovers with 37/25/90 shooting splits. Since then, he's averaging 14.4 points, 3.3 rebounds, 4.9 assists and 3.0 turnovers with shooting splits of 38/36/83. He's barely played half a season's worth of NBA basketball.

Sharpe exploded as a player to watch at the end of last season when he averaged 23.7 points, 6.1 rebounds and 4.1 assists in the Blazers' final 10 games. He showed during the early part of this season that that wasn't a fluke.

With Simons injured, the 20-year-old was once again a focal point of Portland's offense. In the first 22 games of '23-24, Sharpe averaged 18.8 points, 5.6 rebounds, 3.6 assists and 1.0 steals in 37 minutes per game. He shot 42.6 percent from the field on more than 15 shots a game and hit 36.5 percent from three on more than 6 attempts per night. He averaged 4.4 free-throw attempts and hit 82.3 percent of those, too.

Shaedon was showing a sophomore season jump similar to Tatum's. Injuries derailed that, however, and Sharpe could miss the rest of this season after undergoing core muscle surgery. It's a significant blow for someone who needs the developmental minutes as much as he does, but Sharpe proved over six weeks that he has superstar upside.

If either Scoot or Shaedon becomes the Blazers' franchise cornerstone for the next decade-plus after Lillard made room for them, Portland could end up as the winner of the deal.

2. Draft a superstar with one of the Bucks or Celtics picks

If that game-changing player isn't Henderson or Sharpe, Portland can still win the Dame trade if the organization finds one with one of the picks acquired from Milwaukee or Boston.

The Trail Blazers can potentially land three first-round picks from the Bucks: an unprotected 2029 first and two first-round pick swaps in 2028 and 2030. From the Celtics, Portland received a top-four protected first-rounder from the Golden State Warriors that will almost certainly convey this year and a 2029 unprotected first.

The prizes there are the unprotected firsts. Giannis Antetokounmpo will be 34 years old and in his 16th NBA campaign during the 2029 season. Lillard may have returned to Portland and retired by then. Tatum and Jaylen Brown, if he's still in Boston, may be going strong, but Holiday will be retired and Kristaps Porzingis could be lounging on a beach next to him.

The Blazers have their own first-rounder in 2029, as well. With the amount of player movement in the NBA, five seasons is forever. But it's not impossible that the Bucks will be rebuilding by then or that the Celtics will be picking in the lottery.

Winning the Lillard trade comes down to one thing: winning a championship. But to do that, a team needs at least one superstar. If the Trail Blazers have one on the roster or unearth one with the draft capital they got from Milwaukee and subsequently the Celtics, we could look back on September 2023 as the berth of a new era, not the end of an old one.