Tripp was originally drafted by the Colorado Avalanche in the third round, 77th overall, in the 1995 NHL Entry Draft. He re-entered the draft two years later and was drafted by the Calgary Flames in the second round, 42nd overall. Despite being drafted by two different teams, both times fairly high in the draft selection, he would not see NHL level playing time until the 2002–03 season when he played nine games for the New York Rangers. The next season, 2003–04, Tripp played 34 games for the Los Angeles Kings.