Damian Lillard's Blazers Contract Reportedly Had NBA Insiders 'Scratching Their Heads'

Damian Lillard's contract agreement with the Portland Trail Blazers didn't receive unanimous approval from around the NBA.

John Hollinger of The Athletic reported that "people in the league" were "scratching their heads" after Lillard signed a three-year, $42 million deal with Portland.

The star point guard will use the 2025-26 season to rehabilitate the torn Achilles that he suffered in the 2025 playoffs as a member of the Milwaukee Bucks, per ESPN's Shams Charania.

Lillard became a free agent after the Bucks waived and stretched the remaining $103 million on his contract, gaining the financial flexibility to sign center Myles Turner to a four-year deal worth $107 million.

The nine-time All-Star will now be returning to the organization that he spent the first 11 years of his career with, as he's already Portland's all-time leading scorer.

The reported confusion from NBA insiders regarding Lillard's agreement with his former team could stem from the fact that the 35-year-old is joining a Trail Blazers squad that isn't a threat in the Western Conference, missing the playoffs in each of the past four seasons.

Lillard also reportedly received offers from 2025 playoff squads such as the Boston Celtics, Golden State Warriors, Los Angeles Lakers and Minnesota Timberwolves before choosing to return to Portland.

Once he returns from his Achilles injury, the Trail Blazers will need to manage his minutes alongside veteran Jrue Holiday and former No. 3 overall pick Scoot Henderson.

Still, Lillard's contract could become a steal if he's able to recapture the individual production that he displayed prior to the injury.

He averaged 24.9 points, 7.1 assists and 1.2 steals per game while shooting 44.8 percent from the field and 37.6 percent from behind the arc during his 2024-25 campaign with Milwaukee.