In the 2022-23 NBA season, Damian Lillard had arguably the best year of his career, averaging 32.2 points, 7.3 assists, and 4.8 rebounds. It was a career-high for Lillard in points per game, resulting in an All-NBA Third Team selection. Despite his efforts, the Portland Trail Blazers finished the season with a 33-49 record, further solidifying that they didn’t have enough talent surrounding Lillard to be considered serious playoff contenders.
Last offseason, the Blazers were among the most discussed teams in the NBA. All eyes were on the front office and General Manager Joe Cronin following the news that their franchise point guard was disgruntled about the Blazers’ roster construction. Justifiably so, as Portland was seemingly in “no man’s land,” straddling the line between rebuilding and contending for a playoff spot, which many analysts would agree is the worst position a franchise could be in.
Cronin had a monumental decision that would impact the entire NBA. He could trade their No. 3 overall draft pick for another co-star to pair with Lillard to keep him satisfied enough to spend the remaining years of his prime in Portland. Or, he could rebuild around their young assets and draft picks. Ultimately, Cronin traded Lillard to the Milwaukee Bucks in a blockbuster three-team deal involving the Phoenix Suns.
Milwaukee’s Struggles and Lillard’s Adjustment
Fast-forward to this season. With the addition of superstar Damian Lillard, Milwaukee aimed to win their second title in four years. Instead, they had a season in flux, finishing third in the East with a 49-33 record.
Their new star trio of Lillard, Giannis Antetokounmpo, and Khris Middleton had productive glimpses throughout the season. Still, they couldn’t string together a healthy and consistent enough run come playoff time, losing in the First Round to the Indiana Pacers in six games. Giannis missed the entire series due to a calf strain, while Lillard also missed two games with an Achilles injury.
Milwaukee’s lack of depth was apparent throughout the season, particularly highlighted in their must-win Game 6, where Malik Beasley and Pat Connaughton were the only bench players Doc Rivers trusted enough to play for more than five minutes.
Potential for a Reunion
Once again, Lillard can’t be too pleased with his current situation. When he requested a trade out of Portland, he didn’t have in mind another early playoff exit. Lillard has not ruled out a potential return to the Blazers. According to The Oregonian’s Aaron Fentress, Lillard has even said, “I see there being a time where I play for the Trail Blazers.”
Now, with the Bucks’ recent playoff struggles, a Blazers reunion down the road seems like even more of a realistic possibility.
Parallels to LeBron James’ Return to Cleveland
The year after LeBron James left the Cleveland Cavaliers to join the Miami Heat in pursuit of his first championship, the Cavaliers finished with a 19-63 record. They ended up with the first overall pick, which turned out to be Kyrie Irving. While no one on the Blazers’ roster is near Irving’s level, some parallels exist with them acquiring young, promising talent as the Cavaliers did.
They’ll likely have two lottery picks in this upcoming NBA Draft, their own and the Warriors’, which is protected in the top four. Notable players like Anfernee Simons, Scoot Henderson, Shaedon Sharpe, and Deandre Ayton have shown flashes of their All-Star potential. Some promising role players, including defensive-minded rookie forward Toumani Camara, could also intrigue Lillard.
Ever-Evolving NBA Landscape
Lillard has two years remaining in his contract, with a $63.2 million player option for the 2026-27 season. While it doesn’t appear he will leave Milwaukee anytime soon, the NBA landscape is ever-evolving.
If the Blazers show significant progress in their rebuild in the coming years, Lillard may decide to finish his career with the same franchise that took a chance on the young guard out of Weber State in 2012.
