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".
In contrast to expectations, Montgomery's stint with the Canadiens in the 1994–95 season was short-lived, lasting only five games. He was subsequently released and went on to sign with the Philadelphia Flyers, where he appeared in eight regular-season and seven playoff matches. Montgomery is credited with coining the nickname for the formidable trio of John LeClair, Eric Lindros, and Mikael Renberg as the "Legion of Doom".