The 2025-26 Portland Trail Blazers season unofficially begins Monday, when the team holds its annual media day at the Moda Center. Let the countdown to the 2025-26 season begin. He also oozes a level of veteran savvy the rebuilding franchise has been lacking. Off the court, he’s a respected leader with a stellar reputation, and he’ll be asked to provide mentorship for point guard Scoot Henderson and the rest of the Blazers’ young talent. Pundits have questioned how Holiday fits into the Blazers’ rebuilding timeline and there’s no question he’s heading toward the back-end of his career.