Telfair was selected by the Portland Trail Blazers with the thirteenth overall pick in the 2004 NBA draft. On January 1, 2005, Telfair scored 14 points on five-for-eleven shooting, making four of five free throws to go with five rebounds and five assists with one turnover. In February 2005, interim coach Kevin Pritchard promoted Telfair to the team's starting lineup. Telfair notched 6.8 points and 3.3 assists per contest. The Blazers ultimately lost 23 of their final 28 games that season, finishing with the team's worst record since 1973–74.