Montgomery was 61-43-10 in 114 regular-season games behind the Dallas Stars bench from 2018-19. He helped the Stars reach the second round of the Stanley Cup Playoffs in 2019, where they fell just one game short of the Western Conference Final after Pat Maroon's double-overtime goal in Game 7 helped the Blues win the first Stanley Cup in franchise history.
Before being hired as head coach of the Stars, Montgomery had a successful five-year stint as head coach at the University of Denver. In his first season behind the bench, Montgomery led the Pioneers to an NCAA tournament berth and by 2015-16, his club reached the NCAA's Frozen Four. Montgomery eventually led the University of Denver to a national championship in the 2016-17 season and was named the Spencer Penrose National Coach of the Year.
As a player, Montgomery played four seasons at the University of Maine and posted 301 points (103 goals, 198 assists) in 170 games. He is one of three Black Bears to have his number retired by the university, joining former Blues Scott Pellerin and Paul Kariya.
Montgomery was undrafted but signed as a free agent with the Blues, making his NHL playing debut in the 1993-94 season. In 67 games with St. Louis, he posted six goals and 14 assists (20 points). His NHL career spanned 122 games, which also included stints with the Montreal Canadiens, Philadelphia Flyers, San Jose Sharks and the Stars.