For the 1994–95 season however things did not work out and after just 5 games Montgomery was released by the Canadiens. Later in the year he was signed by the Philadelphia Flyers and skated in 8 regular season contests and 7 playoff contests with the Flyers. Montgomery is credited with nicknaming the dominant line of John LeClair, Eric Lindros, and Mikael Renberg the "Legion of Doom".
During the 1994–95 season, however, things did not work out, and after just five games, Montgomery was released by the Canadiens. He then joined the Philadelphia Flyers and played in eight regular-season and seven playoff contests. Montgomery is credited with coining the nickname for the powerful line of John LeClair, Eric Lindros, and Mikael Renberg as the "Legion of Doom".