On June 23, 1994, Carlesimo was hired as head coach of the Portland Trail Blazers. Midway into his first season with the team, the team traded long-time Blazer Clyde Drexler in an effort to rebuild. However instead of falling in the standings, Carlesimo led the team to a winning record and the playoffs in his first season as an NBA head coach. He led the Blazers to the playoffs in each of his three years as their head coach, but was unable to lead the team out of the first round of the playoffs and was fired following the 1996–97 season.