Montgomery played for the Cégep de Saint-Laurent Patriotes in Montreal in 1987–88, before joining the Pembroke Lumber Kings, junior A hockey team in the Central Canada Hockey League in 1988–89. The following season he joined the University of Maine and played four years with the team, winning numerous awards and establishing himself as one of the best prospects in ice hockey. Most notably he was named an All-Star for three consecutive years (1991, 1992, 1993), and was named NCAA tournament's most outstanding player (MOP) when he captained Maine to a record of 42–1–2 and the 1993 National championship. His three third-period goals lifted the Black Bears to a 5–4 comeback win over Lake Superior State in the title game. Montgomery finished his career at Maine as the school's all-time leading scorer with 301 points on 103 goals and 198 assists. His number 19 was retired by Maine, one of three players who have that honour,[1] the others being Hobey Baker Award winners Scott Pellerin (no. 8) and Paul Kariya (no. 9).
Following college, Montgomery was signed by the St. Louis Blues. For the 1993–94 season he skated in 67 contests and scored 20 points, both NHL career highs. Following the season the highly touted Montgomery was traded to the Montreal Canadiens for Guy Carbonneau. For the 1994–95 season, however, things did not work out, and after just five games Montgomery was released by the Canadiens.[2] Later in the year he was signed by the Philadelphia Flyers and skated in eight regular season contests and seven 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".[3] The 1995–96 season saw Montgomery play only five games with the Flyers but he had a career year with the Flyers minor league affiliate, the Hershey Bears of the American Hockey League (AHL). He scored 105 points in 78 games and was named to the AHL Second All-Star Team.
Montgomery was an assistant coach for Notre Dame for the 2005–06 season. In 2006, Montgomery began a four-year stint as assistant coach at Rensselaer Polytechnic Institute. On April 12, 2010, he was named head coach of the United States Hockey League (USHL) expansion franchise Dubuque Fighting Saints. In the team's first year, Montgomery guided the Fighting Saints to a 37–14–9 record and the 2010–11 USHL championship with a three games to one victory over the Green Bay Gamblers. He went on to win the Clark Cup again during the 2012–13 season. In 2013, Montgomery was signed by University of Denver as head coach of their Pioneers men's ice hockey team and led them to a berth in the NCAA tournament. He led the Pioneers to the 2016 Frozen Four. In 2017, his fourth year as the head coach of the Pioneers, he led them to the National Championship game after establishing them as the first-seeded team in the country for the majority of the season.[4] In 2016–17 season he was named the Spencer Penrose national coach of the year.[5][6]
Dallas Stars (2018–2019)
On May 4, 2018, Montgomery was named as the head coach of the Dallas Stars of the National Hockey League (NHL).[7] He led the Stars to their first playoff appearance in three years.
On December 10, 2019, the Stars fired Montgomery for "unprofessional conduct inconsistent with the core values and beliefs of the Dallas Stars and the National Hockey League."[8] At a press conference, general manager Jim Nill said the situation had come to light the previous weekend, and involved "a material act of unprofessionalism" egregious enough to demand Montgomery's immediate firing. He did not offer specifics "out of respect for everyone involved," only saying that it did not involve abuse of players or criminal conduct.[9]Rick Bowness, who joined the team a month after Montgomery's hiring in May 2018, was named interim coach, while Derek Laxdal (who was the head coach of the Texas Stars at the time) would be promoted to the assistant coaching position that was vacated by Bowness.[10]
According to Sportsnet's Elliotte Friedman, Montgomery was fired for "a personal behaviour issue," and the Stars were not divulging details to protect the privacy of both the whistleblower and Montgomery's family.[11] Montgomery told WFAA in Dallas that "there will be a time" when he speaks about the circumstances that led to his firing.[12]
On January 3, 2020, Montgomery announced that he had checked himself into rehab to deal with alcohol abuse. He said that the Stars had made "an appropriate call" in firing him, and that his dismissal made him realize he was living a "damaging lifestyle."[13] On January 7, the Fort Worth Star-Telegram reported that Montgomery was fired in part due to concerns about his drinking. Nill had reportedly confronted Montgomery on numerous occasions about drinking in public. The Stars had been aware of Montgomery's history with alcohol; he had been arrested for DUI in 2008 during his time at RPI.[14]
St. Louis Blues (2020–2022)
On September 16, 2020, the St. Louis Blues signed Montgomery to a two-year contract, serving as assistant coach under Craig Berube.[15]
The Bruins entered the 2023 Stanley Cup playoffs as the favourites for the championship. However, they were ousted in the first round by the Florida Panthers, squandering a 3–1 series lead in the process. The series was dubbed "one of the worst choke jobs in Boston sports history."[19] Much recrimination ensued about Montgomery's coaching decisions, in particular the choice to depart from the team's regular season goalie rotation between Linus Ullmark and Jeremy Swayman to playing Ullmark exclusively despite him dealing with an injury.[20][21] Ullmark defended Montgomery, saying "something that everybody does when things aren't going the way they want to is they're trying to find a scapegoat."[22]
On November 19, 2024, Montgomery was relieved of his head coaching duties following a 8–9–3 start to the 2024–25 season.[23]
Return to St. Louis (2024–present)
On November 24, 2024, five days after his departure from Boston, Montgomery signed a five-year contract to return to the Blues as head coach, succeeding Drew Bannister.[24][25]
National champion
Postseason invitational champion
Conference regular season champion
Conference regular season and conference tournament champion
Division regular season champion
Division regular season and conference tournament champion
Conference tournament champion
