Examining the Damian Lillard Trade Two Years On

Life changed irrevocably for the Portland Trail Blazers on September 27th, 2023 when they traded All-Star point guard Damian Lillard to the Milwaukee Bucks. The moment stands alongside Bill Walton’s free agency in 1979 and trading Clyde Drexler to the Houston Rockets in 1995 as the most earth-shattering personnel decisions in franchise history.

Lillard was not just a 20-point-per-game scorer. He was the heart of the Trail Blazers for more than a decade. He brought them out of the shadows of the failed Brandon Roy-Greg Oden era from the moment he joined the franchise in the 2012 NBA Draft. He won Rookie of the Year, returned his teams to the playoffs, earned multiple All-NBA honors, and even led the Blazers to the Western Conference Finals in 2019. Every billboard, ad campaign, news conference, and national mention of the team featured him.

Since the deal, the Blazers have spent two straight years in the lottery, averaging 28 wins a season. (They averaged just 30 victories the two seasons before he left, in part due to injuries to the star guard.) Lillard has been scoring over 24 points per game in Milwaukee but his team hasn’t made it past the first round of the playoffs. At first glance, it would appear that neither team saw a change in fortunes from the exchange.

The story goes deeper in Portland, though. The Blazers are struggling to find an identity that Lillard provided instinctively. They don’t just lack talent; they lack direction. Part of that is the absence of a lead horse to hitch the wagon to. Nobody on the roster has come anywhere close to Lillard’s charisma and talent. Portland’s search for a new brand continues.

Blazer’s Edge Readers have followed the ongoing saga more religiously than anyone. That’s why we want to pose a question today.

Two years on from the Lillard trade, how do you feel? Do you think it was the right move? Are you in mourning still? Do you think the Blazers would be better off with Lillard still in the fold or are you happier with the new franchise vector? Or did the trade not end up mattering as much as we assumed it would?

What’s your assessment of the Damian Lillard deal in 2025? Give us the thoughts from your heart and head in the comment section.