Revisiting the Lillard Trade One Year Later: Was It Worth It?

The NBA is a title-or-bust league.

Rings are all that matters, and no trade in the league’s storied history has put this philosophy under the microscope more than Damian Lillard’s trade to the Milwaukee Bucks.

It’s been one year since the most consequential trade in the Portland Trail Blazers’ 74-year history. At the end of a torturous summer of 2023 for Blazer fans, news came that the Bucks won a three-month-long sweepstakes for the top-75-all-time player. 

Lillard Gave Portland Everything

Dame had everything he had ever wanted in the City of Roses. Growing up in a tough part of Oakland, making it to the league and changing his family’s trajectory was his primary goal. Not only was Portland where his children were born and being raised, Lillard moved his mom, brother and cousins there. His best friends followed him to Portland.

His life in Portland was “set up perfectly”, he told The Oregonian.

All Dame wanted was to give back to the city that gave him everything. Off the court, he was a champion in the community. He recently received the first-ever Bill Walton Community Impact Award from the Blazers for initiatives like his RESPECT program and the Lillard Foundation.

On the court, he was a unanimous Rookie of the Year. He hit the franchise’s most iconic game-winner and did it again five years later. He was an Iron Man for nearly a decade, playing in all 82 games each of his first three seasons and never missing 10 games in the first seven. He dragged Portland to the Western Conference Finals in 2019, the furthest the franchise had been in a generation. 

Damian Lillard gave everything he had for Portland, and they couldn’t put the pieces around him to compete for the one thing that was eluding him and the team— an NBA title.

Dame was patient. He sat out the end of two consecutive seasons so the team could tank for a high draft pick, something that undoubtedly irked the ultra-competitor. The tanking worked and the Blazers got what they wanted in the number three overall pick in the 2023 NBA Draft. 

Lillard wanted to stick with the organization that drafted him, in the city he and his entire family called home, if there was a semblance of competitiveness and mutual respect for his goals.

Franchise Outlook Finally Changed

But when Portland didn’t make a trade for a veteran player and instead took Scoot Henderson, who played Lillard’s position, with the third pick, new General Manager Joe Cronin made it clear with his actions, rather than his words, that it was Portland who was ready to move on first.

So Lillard asked for the first time, despite receiving incessant pressure from the media for years, to be traded to a competitor. His primary request was the Miami Heat, but when this news was made public and the Heat did not come to the table with an offer Cronin liked, the Blazers GM sat on his hands until he felt the time was right. 

All Blazer fans agreed that Cronin needed to trade Lillard if the goal was to win a title, and most agreed that Portland got a substantial haul that would provide them with current and future assets to work with.

Bucks + Lillard = Championship?

All NBA fans agreed that Lillard joining Milwaukee made the Bucks an immediate competitor for an NBA title. Vegas concurred, putting them even with the Celtics as favorites to come out of the East before the season.

But when success is so black and white when 31 out of 32 teams every year are considered failures, trades that are unanimously considered wins for all parties can sour very quickly.

The Bucks’ season was turbulent. They hired a rookie head coach in Adrian Griffin who began his tenure by causing Assistant Coach Terry Stotts, Lillard’s Head Coach in Portland for nine years, to quit.

Halfway through the season, while sitting with a top-two record in the league, Milwaukee fired Griffin to replace him with Doc Rivers, a questionable decision that would backfire. The Bucks eventually ended as the third seed in the East and would lose to the Indiana Pacers in the first round. Never mind that Giannis was hurt for that series— results are what matters in the NBA, not the process.

NBA Players’ Personal Lives Often Overlooked

On top of a frustrating journey on the court, Lillard felt out of place and lonely off the court. He told Sports Illustrated’s Chris Mannix about living in Milwaukee, “Seriously, I don’t have much of a life. But that’s what comes with making a big-boy decision. You got to be down for that and figure it out.”

Across the country, where the rest of the Lillards still resided, things weren’t going much better for the Blazers. Lillard’s replacement — the supposed next franchise cornerstone for Portland’s new era — was struggling mightily. Fans have aggressively thrown the “bust” tag at Scoot Henderson, whether justly or not. Their secondary star Shaedon Sharpe missed two-thirds of the season with an abdominal injury. Portland wasn’t supposed to be good, and they weren’t.

Now Portland goes into its second year of a rebuild, but it will be the fourth season in a row where they, at least in part, are tanking. Henderson’s season will be placed under a microscope. If Portland doesn’t end up with a top-three pick in the 2025 draft, panic will ensue. The road to relevancy is a long one.

Year 2 (still 1) for Dame in MKE

Milwaukee heads into their second season in the Lillard era with their rivals in Boston coming off a dominant title run. While they reloaded with cheap veteran talent for the second year in a row, the Celtics retained their entire championship lineup including Jrue Holiday, whom they unknowingly gave to Boston for Lillard.

If Dame had stayed in Portland, the Blazers would not have won a championship with him on the roster. But in that final season, he averaged 32 points per game. He had 50, 60 and 71-point performances. He hit a game-winning three-pointer in the All-Star Game representing Portland. He was having personal success, perhaps more so than at any other point in his career.

But the Blazers weren’t winning a title. National media reminded Portland fans of that almost every day as if they actually cared for the city’s success.

It will be a while before either side receives the final verdict on whether the Lillard trade was a success or not, but there is only one barometer that NBA fans and media will use— did they win a title, or did they not?