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There is no denying that Damian Lillard loves the Portland Trail Blazers following his decision to reunite with the team in free agency, but the organization certainly made it difficult for him to refuse its offer. Owners do not typically award a three-year, $42 million contract to a 35-year-old recovering from a torn Achilles tendon unless they are confident the player will reward their investment. Although the Blazers are obviously inclined to take care of a franchise legend like Lillard, there are undeniable risks from a basketball standpoint.
Because Portland is in the throes of a rebuild, it risks stunting the development of Scoot Henderson and its other young players by potentially making the aging Lillard a focal point of the offense during the 2026-27 season. Despite the elation Rip City is experiencing after this celebrated homecoming, one has to wonder if this signing makes sense based on the trajectory the Trail Blazers are currently navigating. That question may not be all that relevant, depending on who you ask.
Apparently, some within the league believe there there is a strong motivating factor that could be influencing the team's offseason approach. “If you’re one of those people who likes to plot out multi-layered conspiracies with charts and arrows, there’s also plenty of room for that type of thinking,” The Athletic's John Hollinger writes.
“Between the impending sale of the team, the Lillard move and the surprise selection of Chinese center Yang Hansen in the first round of June’s draft, a lot of the conversation in Vegas was about whether the Blazers are making purely basketball decisions right now. How much does the optics for a potential buyer influence the basketball choices?”
Blazers great Damian Lillard is certainly good for business
The idea that the Paul Allen estate would make moves designed to strengthen a potential ownership sale does not appear too far-fetched. This is a business, after all, and a household name and local hero like Damian Lillard is easy to pitch to prospective buyers. The star point guard and Blazers' all-time leading scorer (19,376 points) is an ideal person to serve as the face of the franchise during a power transition, particularly because of the profound connection he shares with the community.
Lillard potentially ending his Hall of Fame career in Portland ($14.1 million player option for 2027-28 campaign) could help fans stay optimistic amid possible concerns regarding a new regime. Beyond the financial implications that come with having a marketable talent on the roster, which is arguably amplified due to the reunion element, Lillard's presence could positively affect the Trail Blazers' basketball product.
The 2018 All-NBA First-Team selection and four-time All-NBA Second-Team selection posted 24.9 points and 7.1 assists while shooting 37.6 percent from beyond the arc before his 2024-25 season met its brutal end. Although he is expected to miss the entire 2025-26 campaign, Lillard can still share some of the knowledge he has gathered in his decade-plus run in The Association.
Oftentimes, a valuable veteran can hasten a squad's rebuild and better position it for long-term success. And this veteran may just be the greatest player to ever don a Blazers uniform. Regardless of Portland's motives, this sequel will generate significant interest in the next couple of years.
