Flyers coaches who won big after leaving the team

While some of these coaches found moderate success in Philadelphia, it wasn't until leaving that they won the NHL's greatest prize.
Rangers coach Mike Keenan celebrates with the Stanley Cup after defeating Vancouver 3-2 in Game 7 of the Stanley Cup Final at Madison Square Garden, June 14, 1994.
Rangers coach Mike Keenan celebrates with the Stanley Cup after defeating Vancouver 3-2 in Game 7 of the Stanley Cup Final at Madison Square Garden, June 14, 1994. | Frank Becerra Jr./The Journal News

In this Coaching Benchmarks series, we will take a look back at what happened to the former coaches of the Flyers after they stepped out from behind the bench in Philadelphia. The Backfire Group looks at coaches who resulted in a backfire in one capacity or another. Most found a way to win it all elsewhere, though.

Mike Keenan (1984-88)

When you think of the nitty gritty style of hockey, the first thing that comes to mind is the Broad Street Bullies. Looking behind that, you will see Mike Keenan. Keenan, who started his coaching career in Philadelphia, was known for his gruff approach, pushing his players to give their all.

“Iron Mike” began his coaching career in Philadelphia in 1984 and won the Jack Adams Award at the end of his rookie coaching campaign. He spent four seasons with the Flyers, pushing them to four straight playoff appearances, three straight first-place finishes in the division, and two trips to the Stanley Cup Final, where they lost to the dynastic Oilers in both series.

In their second SCF meeting with the Oilers, they stood toe-to-toe with the powerhouse group, losing 3-1 in Game 7. Goaltender Ron Hextall was named MVP of the series and the playoffs.

Keenan was out after the 1987-88 season, quickly landing a new position in Chicago. He led the Blackhawks to four straight playoff appearances, including one trip to the Final, though they lost to the Pittsburgh Penguins in 1991-92.

As a rough-and-tumble coach, Keenan quickly wore out his welcome, spending no more than four seasons with any team. His shortest stint was also his best. In the 1993-94 season, he got 112 points out of the first-place New York Rangers before winning the Stanley Cup that postseason.

Things allegedly fell apart between Keenan and the Rangers' General Manager, Neil Smith, and he left the team citing breach of contract. The team fired back, stating the breach was a one-day delay in a bonus payment due to Keenan. He later called it the “biggest disappointment” in his career.

Keenan then made it through parts of three seasons in St. Louis before being fired in December of 1996. The Blues made it to the postseason in his first two seasons and continued to the 1996-97 postseason after his departure.

Counting that post-dismissal berth in 97, Keenan’s teams made it to playoffs for all 12 of his seasons behind the bench, including one Stanley Cup championship and three other trips to the finals. Then the dark times began for Keenan.

Between 1997 and 2004, he made his way in and out of Vancouver, Boston, and Florida, never making the playoffs in any of those seasons, and getting booted from Boston after only one season.

In 2007, Keenan ended the three-year gap in his resume by taking up the coaching job in Calgary. He took the Flames to two straight playoff appearances, losing in the conference quarterfinals each time.

Keenan eventually made it to the KHL in 2013, where he coached Magnitogorsk Metallurg for a little over two seasons, winning the Gagarin Cup in his first year there and being booted in 2015, his third season, despite having a winning record.

In 2017, Keenan joined China’s only KHL team, the Kunlun Red Star, as GM and coach, where he was fired twice that season, first as GM and then as coach. The team had a winning record at the time of his departure.

He then landed the head coaching gig for the Italian National Team in 2022 but stepped down in 2024 after open-heart surgery.

Mike Keenan’s flame burned bright but never for long. He won the Jack Adams Award in Philadelphia at the end of his rookie coaching season. He took the team to the Stanley Cup Finals twice and likely would have won at least once, had they not faced prime Wayne Gretzky and the Edmonton Oilers both times. He had some remarkable accomplishments that only Keenan could have, leaving a team after one year, including a Stanley Cup Championship, and getting fired twice by the same team in the same season while having a winning record.

Craig Berube (2013-15)

Berube played 1,000 games in the NHL over 17 seasons, seven with the Flyers, the team that gave him a chance as an undrafted free agent. Hitting the ice for 1,054 games is impressive, and even more so when you make your living with your fists. “Chief” finished his NHL playing career with 61 goals, 98 assists, and 3,149 penalty minutes, dropping the gloves over 240 times.

In his two seasons behind Philly’s bench, Berube ended with a first-round playoff exit in 2014, followed by slipping out of contention the following year. The Flyers had winning seasons both years, however.

In 2016, he was hired as the head coach of the AHL’s Chicago Wolves. The following season, he returned to the NHL as an assistant coach of the St. Louis Blues.

In November 2018, he was named interim coach of the Blues and became the second interim coach in NHL history to win a Stanley Cup (2019). He led the Blues to four consecutive playoff appearances and took the head coach gig in Toronto before the 2024-25 season. His Maple Leafs finished in first place and are taking on the defending champion, the Florida Panthers, in the second round of the playoffs.

After leaving Philadelphia, Craig Berube headed to St. Louis. There, he became the second coach still holding onto the interim tag to win the Stanley Cup when the Blues won in 2019. He is now in Toronto, where he led the Maple Leafs to a first-place finish, and they are still in contention for the Stanley Cup.

Bill Dineen (1991-93)

Dineen worked his way up the WHA and AHL before making it as a coach in the NHL. He won championships at both of those levels with the Houston Aeros (1973-74, 1974-75) and the Adirondack Red Wings (1985-86, 1988-89). He won the Louis A.R. Pieri Memorial Award for best AHL coach in 1984-85 and 1985-86.

Dineen joined the Flyers as a scout in 1990 and was promoted to coach the following season. The father of future Flyer Kevin Dineen, he spent two seasons behind the bench of two bad Flyers teams before returning to a scouting position with the team from 1994-97.

Unlike the other coaches in this group, Dineen did not go on to win a Stanley Cup elsewhere, but he may have been the most prescient person in hockey. As the Philly hockey world salivated over the bringing of Eric Lindros to Philly, he disagreed, preferring to keep Peter Forsberg, et al. in Philly.

Bill Dineen was a talented scout and successful coach at the WHA and AHL levels. He suffered behind the bench of two bad Flyers teams before returning to scouting. Soon thereafter, Dineen retired to the Adirondack area near his beloved Red Wings, holding onto one of the biggest “I told you so's” in Philly hockey history.