Damien Lillard and the Portland Trail Blazers are not expected to find success with their team this season, but the 35-year-old’s signature could have set the team for their future.
The Portland Trail Blazers have not won a postseason in the last four seasons, and have put their efforts to the right to add veteran point guard Juloo Holiday and bring back franchise legend Damien Lillard on a three-year deal.
The holiday is soon approaching the end of his prime, with 35-year-old Lillard missing out on everything for next season with Torn Achilles. As a result, the Blazers are expected to miss a back-to-back playoffs for the fifth season, but they form a clear, defence-first identity.
The holidays are expected to replace Scoot Henderson with a lineup that is a clear upgrade, but the reality is that the Blazers are still a few times away from their competition.
The Western Conference is better than ever, with teams like Thunder, Rockets, Nuggets, Lakers, Clippers, Timberwolves, Mavericks, Grizzlies, Spurs, Warriors and even King going better than Portland next season.
Lillard will not play for a minute next season, and will be playing the role of “assistant coach” until he is ready to return.
“They pay Dame to become an assistant coach on their entry,” said ESPN’s Brian Windhorst. “But they traded for Jrue Holliday, a $100 million investment to win right away, but they don’t have this young team and star players either until next year.”
Windhorst and most fans “will not consider him a playoff team” next season, but after years of approaching the bottom of the rankings, Portland is finally in fashion.
The 35-year-old’s signature with a career-changing injury doesn’t look like a wise move as the franchise heads into the future, but the terms of his contract will be given to Portland enough runways.
By the time he is ready to go back to 2026-27, they will be able to open about $30 million in cap space and kick out the roster of Lillard, Holiday, Shedon Sharp, Donovan Klingan, Hansen Yang, Henderson, Jerami Grant, Deni Avdija and Tumani Kamala.
In addition, they can go hunting at a free agency.
“There are a few things to note here: when Damien Lillard signs that deal, the second year comes down,” Bobby Marks retorted. “Portland will be in a position to go out for free-agent shopping next offseason. They will get the largest player. The expansion of Shaedon Sharpe and Toumani Camara certainly plays a role.”
Also, the Blazers have yet to be informed of drafts and trade assets from the trade that first sent Lillard to the Milwaukee Bucks in the first place.
“We’ve forgotten this. Damian Lillard has been traded for Milwaukee,” Marks added. “Remember what’s back. Portland manages the first round picks of the Milwaukee Bucks in 2028, 2029 and 2030. So they are certainly in a position to add free agents.”
Between draft capital, financial flexibility and young talent already on the roster, the Blazers have many promises and reclaiming the franchise legend to oversee growth could have been a perfect move.