Wilson played Junior A hockey with the California Kings and the Dubuque Saints. In 1993-94, he enrolled at the University of North Dakota and scored 33 points as a WCHA freshman. That season, he paced the league with 147 penalty minutes. In 1994-95, Wilson scored 23 points in 31 games. He then turned pro with the AHL's Cornwall Aces and scored eight points in eight regular-season games. In the playoffs, he scored seven points in 13 games. In 1995-96, Wilson scored 21 goals and 34 points as a pro rookie.

On November 29, 1995, he made his NHL debut with the Colorado Avalanche with a goal against the Devils. In 1996-97, after nine games with the Avalanche, Wilson was traded on November 22 with Anders Myrvold to the Boston Bruins for a 1st-round draft pick. He scored 17 points in 40 games with the Bruins as the team missed the playoffs for the first time in 30 years. In 1997-98, he played 28 games for the Bruins as the team improved 30 points to get back into the playoffs. Wilson played one post-season game that spring. In 1998-99, he played 22 regular-season games and eight playoff games as the team reached the second round. In 1999-00, he played 40 games for the Bruins.

On July 7, 2000, he signed as a free agent with the Phoenix Coyotes. That season, he joined the NHL ranks full time and scored 18 goals, 31 points and 127 hits in 70 games before injuries limited the former first rounder to a mere 47 games in 2001-02 and 31 games in 2002-03. After beginning the 2003-04 season in Phoenix, Wilson was dealt to the Pittsburgh Penguins in February of 2004 for future considerations.

On the international stage, Wilson represented the U.S. at the 1995 World Junior Championships and the 2001 World Championships.