Simon was a member of the Washington Capitals when they went to the Stanley Cup finals in 1998. He had been enjoying great offensive success that season until a shoulder injury knocked him out for much of the playoff run. He underwent season-ending shoulder surgery in December 1998. He was the team's leading goal scorer in the 1999–2000 season with 29 goals in 75 games. He also made it to the Stanley Cup finals with the Calgary Flames in 2004, and played for the Flames for two seasons before being signed as a free agent in 2006 by the New York Islanders and was then traded to the Minnesota Wild for a 6th round draft pick.
