Damian Lillard is set to make a surprising comeback to the Portland Trail Blazers on a three-year, $42 million deal that includes a player option for the 2027-28 season and a no-trade clause. This return was announced amid plans for Lillard to rehabilitate his torn left Achilles throughout the entire 2025-26 season, targeting a comeback on the court during the 2026-27 season.

This unexpected move impacts not only the Blazers but also the broader NBA landscape, raising questions about Portland’s rebuild strategy, team chemistry with young talent like Scoot Henderson, and why Lillard chose to rejoin his original team instead of opting for a championship contender. The deal also alters the futures of multiple franchises and players connected to this storyline.

Damian Lillard’s Personal and Professional Victory

For Damian Lillard, this deal represents a significant triumph after a challenging phase in his career. Lillard suffered a devastating Achilles injury shortly after bouncing back from a blood clot, leading to an uncertain future. After the Milwaukee Bucks waived him—stretching the remainder of his $112.6 million contract across two years—he found himself without an NBA home.

Now, Lillard returns to the Trail Blazers where he began his professional journey, regaining substantial control over his career with the inclusion of a no-trade clause. Financially, the new contract guarantees more than he would have earned had he remained with the Bucks under the existing plan. This comeback also allows Lillard to rehab closer to his children, an arrangement that became a top priority for the star player, as reported by ESPN’s Shams Charania.

Considering all factors, there appears to be no apparent downside for Lillard himself in this agreement.

Contenders Miss Out on an Affordable Damian Lillard

Many NBA fans and analysts expected Lillard to join a contender on a modest contract, possibly a one-year deal with a player option, allowing him to return midseason and compete for a championship. The idea was that this plan would enable Lillard to secure a larger contract the following offseason after demonstrating his recovery and value.

Among the teams reportedly interested was the Boston Celtics. According to Boston Globe’s Gary Washburn, Celtics star Jayson Tatum was actively recruiting Lillard, envisioning both players recovering from their Achilles injuries together and leading the team in a title run for the 2026-27 season. The fit seemed ideal, filling gaps in Boston’s roster while managing financial constraints.

However, these plans evaporated with Lillard’s decision to return home, leaving contenders like the Celtics without the anticipated boost from one of the league’s premier guards.

Milwaukee Bucks Reduce Financial Burden with Lillard’s New Contract

The Milwaukee Bucks find themselves benefiting financially from Lillard’s new deal with the Blazers. While the team remains responsible for the majority of his previous contract, a portion of the money owed to Lillard will now be offset by his $42 million agreement.

NBA salary cap expert Bobby Marks explains that the offset applies only to the original term of Lillard’s contract, covering the next two seasons, and the cap relief will not be reflected until after the current season ends. Overall, the Bucks will save approximately $11.7 million, with Lillard’s dead cap hit decreasing from $22.5 million per year through 2029-30 to roughly $20.2 million.

Though the savings are modest, they represent a financial win for Milwaukee given the circumstances.

Implications for Scoot Henderson’s Development and Role

The Blazers’ decision to welcome Lillard back does not indicate they are abandoning high draft pick Scoot Henderson. However, it does add pressure on Henderson to demonstrate accelerated development as he approaches his third season and possible contract extension eligibility next summer.

With Lillard’s return, Henderson faces intensified scrutiny regarding his ownership of the team‘s offense. Last season showed encouraging progress for Henderson, who established himself more firmly as a key offensive contributor, but the bar is now higher.

Additionally, the acquisition of Jrue Holiday, a costly and experienced veteran, further complicates Henderson’s path to a full-time starting role. Holiday’s presence suggests the team might rely more on veteran wings and guards, raising questions about who will assume primary leadership on the floor once both Lillard and Holiday are back in the lineup. Henderson has spent much of his young career coming off the bench, raising concerns about his long-term position as the franchise’s lead guard.

Positive Outlook for Big Men Yang Hansen and Donovan Clingan

The return of Damian Lillard also creates promising opportunities for the Blazers’ frontcourt players Yang Hansen and Donovan Clingan. Last season, Portland struggled to maximize their big men’s effectiveness on offense, and having a player of Lillard’s caliber on the court should improve spacing and passing dynamics.

Lillard’s ability to draw defensive attention will open up more room under the basket, allowing Hansen and Clingan to operate with greater freedom and receive higher-quality touches. His vision and precision in passing will also provide them with clearer pathways to contribute offensively.

This benefit could diminish if Scoot Henderson makes significant leaps in his third year, if fellow forward Deni Avdija continues to move forward, or if the Blazers add more playmakers prior to the 2026-27 season. Nonetheless, Lillard’s influence is expected to help streamline the offensive roles of Portland’s big men.

Remaining Questions Surround Young Talents and Team Composition

The futures of young players like Shaedon Sharpe remain uncertain. Sharpe, eligible for his rookie-scale contract extension, confronts some of the same challenges as Henderson. He fits naturally beside Lillard since he is not a point guard, but with Jrue Holiday, Henderson, and Lillard in the backcourt mix, the competition for minutes and roles intensifies further.

Jrue Holiday’s Position Faces Uncertainty

With the arrival of Lillard, Jrue Holiday’s place on the team appears tenuous. It’s widely presumed that Holiday could be traded before the 2026-27 season starts, although it’s also possible he remains with the team if no suitable offers materialize. How Holiday reacts to a likely move—whether with relief or frustration—will depend on timing and circumstances. His contract, spanning three seasons at $104.4 million, adds further complexity to any potential trade transactions.

Fast-Track Rebuilding Strategy for 2026-27 and Beyond

The Blazers’ moves—including acquiring Holiday and bringing back Lillard—indicate they intend to accelerate their rebuild no later than next summer. This aggressive approach may appeal to other teams planning to tank during the 2026-27 season, as Portland’s roster composition will offer fewer obstacles in a competitive landscape.

Free Agent Market Impact for 2025

Portland’s commitment to Lillard means the team has little cap space left for other free agents in 2025. Restricted free agents like Quentin Grimes and Cam Thomas, who might have counted on Portland to offer mid-level contracts, will need to seek opportunities elsewhere, as the Blazers will not be in a position to make significant offers beyond Lillard’s contract.

Overall, Damian Lillard’s $42M Blazers return profoundly shapes not only Portland’s future but also the movement and strategies of other NBA teams. It shifts expectations for rising stars on the Blazers roster, influences free agent dynamics, and leaves contenders reconsidering their options for adding front-line talent. Lillard’s homecoming promises dramatic implications heading into the 2026-27 NBA season.

“Go ahead and search for the downside here if you’re so inclined. There isn’t any—not for Dame, anyway.” —Dan Favale, National NBA Writer
“Lillard plans to rehab his torn left Achilles for the entire 2025-26 season before returning to the court in 2026-27.” —Shams Charania, ESPN
“As ESPN’s salary-cap guru Bobby Marks notes, the offset only applies to the original length of Dame’s contract—so, the next two years.” —Bobby Marks, Salary Cap Analyst
“Simply put, Lillard is an icon in Portland. He will be treated like royalty under the circumstances of his return.” —Dan Favale, National NBA Writer
“Jayson Tatum, as one example, was reportedly recruiting Lillard on behalf of the Boston Celtics.” —Gary Washburn, The Boston Globe
“Lillard returning closer to his children became a top priority for him.” —Shams Charania, ESPN
“The Blazers plan to hit the turbo button no later than next summer.” —Dan Favale, National NBA Writer