Damian Lillard’s decision to leave the Milwaukee Bucks and return to the Portland Trail Blazers has sent shockwaves through the NBA. Instead of pursuing a clearer path to a championship, Lillard chose loyalty and familiarity over opportunity, signaling a powerful emotional connection to Portland. This move, occurring as Lillard recovers from a torn Achilles, raises serious questions about both his future and the Blazers’ trajectory.
Why Lillard’s Return Defies NBA Expectations
After the Bucks bought out Lillard’s contract, many expected the star point guard to join a team with a better chance at winning a title. Yet Lillard prioritized returning to the city where he crafted his legacy. This choice surprised NBA insiders, who recognize that Portland remains far from contending in the tough Western Conference.
John Hollinger of The Athletic noted that from Lillard’s perspective, the deal made sense in terms of both location and financial security, but for the Blazers, the move introduces complications. The league’s reaction reflected uncertainty and confusion about the decision’s logic.
Critical concerns revolve around timing. Lillard will be 36 when he resumes play in Portland, coming off a challenging injury recovery that can be difficult even for younger athletes. Given the Western Conference’s depth, doubts linger about whether Lillard can perform at his previous elite level.
Financial and Roster Challenges for Portland’s Rebuild
Portland’s rebuilding plans face new hurdles with Lillard’s return, especially since the team is still young but tied financially to several veterans. Alongside Jrue Holiday and Jerami Grant, Lillard’s contract extends through the 2027-28 season, potentially limiting salary cap flexibility if all three players opt into their final years.
Importantly, Lillard’s salary remains substantial. Hollinger highlighted that the Blazers will pay him approximately
$64 million for the next two seasons,
which includes the Bucks’ stretched payments.
This financial commitment complicates roster construction, particularly regarding Portland’s backcourt. The team recently traded Anfernee Simons and must manage the presence of Scoot Henderson, a promising young point guard developed over two seasons.
As Hollinger points out, the tension between Lillard’s expected comeback in 2026 and Henderson’s potential breakout season in 2025-26 creates multiple risks for the Blazers’ lineup and player development.
There are a million ways this can go wrong.
—John Hollinger, NBA Analyst
Hollinger further explained,
Lillard is a dead-money roster spot for 2025-26 and leaves the Blazers very thin in the backcourt after the Anfernee Simons trade; one presumes Portland will land a veteran point guard with its final roster spot (the Blazers can sign a veteran’s minimum contract and stay a few pennies below the tax line),
Potential Impact on Team Chemistry and Future Prospects
The timing of Lillard’s return could create a challenging environment as he aims to reestablish himself alongside emerging talent. Hollinger warned that,
Lillard will come back in the fall of 2026 wanting to prove he’s that Damian Lillard, which could be problematic if Henderson emerges in 2025-26; that combined with Lillard’s status in Portland could lend itself to some Kobe-in-2016 vibes,
indicating potential tension in leadership and court roles.
Despite these complications, Lillard’s return immediately energizes the Blazers’ fan base. His clutch performances and historic moments in Portland’s history are undeniable, and his commitment to coming back signals a desire to continue building his legacy with the team he has long represented.
No matter the uncertainties, Damian Lillard Blazers Return marks a pivotal moment for both the franchise and the player, setting the stage for a high-stakes and emotionally charged chapter in Portland’s evolving story.