What would that imply, given the entirety that’s came about?
He took a few seconds to contemplate it.
When the Dallas Stars named Montgomery head coach on May 4, 2018, he was once on the upward thrust.
He had gained all over the place he went. He was once captain grab of the nationwide champion 1993 Maine Black Bears, one of the highest collegiate offensive gamers of his technology, and wrung 122 NHL video games out of a body he describes as “tall as a fire hydrant.”
After turning to coaching, he won two USHL titles in three years with Dubuque and an NCAA title at Denver in 2017. He had a sharp hockey mind, a no-nonsense communication style, and a quick wit.
He additionally had a consuming drawback.
Montgomery wasn’t a daily consumer, he has said, but he would binge to the point of blackouts. A 2008 arrest for driving under the influence, during a coaches’ retreat near Naples, Fla., was an early warning that his usage was out of control. In Dallas, general manager Jim Nill told him the same.
On Dec. 10, 2019, the Stars announced that Montgomery had violated the organization’s conduct code. Nineteen months into his tenure, coming off a surprise playoff run the season before — and with two-plus years and nearly $4 million left on his contract — Montgomery was fired from his first NHL coaching job.
Now approaching three years of sobriety, Montgomery doesn’t wish to discuss that part of his journey. During a May 2020 interview on TSN in Canada, he acknowledged his dismissal was deserved, and he had stopped trying to fix his problem by himself.
“It’s tough when you face your family and you’ve been dismissed, when you had the best job in the world,” said Tommy Cacioppo, his childhood best friend from Montreal.
Montgomery’s recovery included three weeks each of inpatient and outpatient rehab, individual and family therapy, a daily conditioning program, meditation, and journaling. A couple of friends noted his Catholic faith as another strengthening factor.
The Stars supported him, publicly and privately (Nill, through a spokesperson, declined comment but wished Montgomery well). Montgomery’s connection to St. Louis, where he signed his first pro contract and met his future wife, helped him land with the Blues. Hired as an assistant in September of 2020, he worked there for two seasons.
“He’s doing everything right,” Cacioppo said. “His family comes first and now Boston’s part of his family. He takes pride in what he does. He’s got that second chance. He’s not going to [mess] it up.”
An early training bent
A few weeks into his new job, Montgomery was sitting on a bench outside the team’s practice rink in Brighton. On a breezy, humid, cloudy morning, the 53-year-old coach was in golf wear and sandals, the standard mid-August uniform of his profession.
Montgomery took a sip from his cup. It was a caramel miso latte, a bit savory, a bit sweet. Not his usual morning flavor, but he wanted a latte, it was first on the list of specials, and the barista talked it up. So why not?
He didn’t need a jolt of caffeine to get his mind racing.
He was in the process of meeting some 60 Bruins players and prospects, learning what makes them tick. He was scouting their film, trying to figure out a lineup that can keep his team in a playoff spot through anticipated early-season turbulence. He and his wife, Emily, were settling their four children into Winchester schools and sports.
He was sitting a five-hour drive south of Montreal’s Rosemont section, where he grew up in the shadow of Olympic Stadium.
While Boston was in its post-Orr renaissance of the late 1970s, Montreal was in the middle of a Canadiens dynasty. Hockey was religion. Cacioppo recalled four or five youth teams in every 2- to 3-mile radius, the leagues run by local churches.
Their bond formed at age 10, at a hockey camp run by Montgomery’s maternal uncle, Bob Beale, who worked as an NHL agent. The camp was started by Beale, Habs great Jean Beliveau, and co-owner Peter Bronfman to bring together Francophone and Anglophone youth, putting them on mixed teams with no score kept.
Montgomery was “the loudest kid there,” Cacioppo said, and quickly became his “only Irish friend.”
The school lives on as Canada Sports Friendship Exchange Programs, funded by the Canadian government. For Montgomery, it was a critical place of development. He began teaching there at 17, reverting back to student when NHL players such as Mike Krushelnyski and Larry Robinson would come to speak.
When Scotty Bowman confirmed up, he took notes.
“I would just sit there and ask him a million questions,” said Montgomery, who still connects with the 89-year-old Hall of Famer.
Bowman, mastermind of that Montreal dynasty and arguably the greatest NHL coach ever, “loved talking hockey, so he’d answer them all. So I guess that was kind of a good mentor who helped me. He helped me open some doors.”
Meanwhile, with the midget-AA Montreal Norois, Montgomery was tearing it up on a line with Cacioppo and Agostino “Aggie” Casale (who later played at Merrimack and in Europe). Montgomery recalled high-scoring, pace-pushing shifts.
“We never had to tell each other what to do,” said Cacioppo, who now owns a window supply company in their hometown. “You can’t teach hockey sense. If you’re a north-south player, pass the red line and dump it in, there’s a million players like that. Guys who hold the puck, make the extra pass, those are the special ones.”
Taking off at Maine
In 1988, Montgomery was an undersized forward who couldn’t get a look from the major Canadian junior leagues in Quebec, Ontario, and Western Canada. He remembered local scouts telling him he’d “never play a day professionally.” He might as well go play in college, they scoffed.
“Trying to delay the real world,” as Montgomery put it, he hooked on with the junior A Pembroke Lumber Kings, northwest of Ottawa. Grant Standbrook, a first-year assistant coach at the University of Maine under Shawn Walsh, had been handed a list of 40-plus players to go recruit.
“By November, I still hadn’t found anybody I really liked a lot,” said Standbrook, now 85 and living in Naples, Fla. “Then I found Jim.”
Montgomery, on his way to a 53-goal, 154-point season in 50 games, “could read the ice, he could make plays, he could finish,” Standbrook said. “He was maybe 5-9. But he was very, very smart.”
In the son of a boxer, Standbrook noticed a long run captain.
“He could jab them if he had to,” Standbrook said. “He said the right things. He brought out the best in people.” It was, he said, Montgomery’s best quality.
“Even back then,” said teammate Garth Snow, later the Islanders goalie-turned-general manager, “he had the mind of a coach. He was almost finishing their sentences when it came to strategizing, adjustments.”
Montgomery took off in Orono, scoring 301 points in four seasons. Walsh, like most coaches, named several captains, but in 1993, the senior was the only one he needed. Montgomery’s connection with supernova freshman Paul Kariya that year turned a good Maine team into a 41-1-2 juggernaut and the state’s most cherished homegrown sports memory.
Snow recalls Montgomery — not Walsh — calling a timeout in the third period of the 1993 national championship game against Lake Superior State. That was in the middle of Montgomery scoring a natural hat trick in the period, off feeds from Kariya.
“The pressure didn’t matter,” said Montgomery’s college roommate, winger Kent Salfi. “He had that inner confidence. Fearless.”
Kariya, who in 2017 revealed a lengthy struggle with concussions, now lives in Southern California. He talks to Montgomery regularly and takes him to a favorite sushi spot whenever he visits. They share a tight, private friendship, strengthened by the times they’ve gotten up off the mat.
Compiling his methods
A light-heavyweight who boxed for Canada at the 1956 Olympics, Jim Montgomery Sr. worked at Shell Oil for about 40 years. He was a refinery hand and union president.
His son, who for two college summers drove around to collect oil samples, was told his father was so good at leading the union that management offered him a position.
The elder Montgomery, who died in 2015, also played basketball, football, and rugby at a Canadian amateur championship level and was a volunteer hockey coach for the East End Boys Club in Montreal.
“He was not only bright but he really understood and cared more about the team,” said his youngest son, whose mother, Dorothy, is in her 90s and still living in Montreal.
“He was always, like, ‘Make the extra pass, your teammates will want to play with you. Make sure no one’s being picked on in the room, that they’re isolated.’ He was always talking about giving and going, moving to get open. That always stuck with me.”
Cacioppo recollects a easy man.
“You played well, you got a compliment. You played like [crap], you were told that,” he said. “Jimmy was never put on a pedestal. He could always do better.”
Montgomery grinded through 12 years of clutch-and-grab pro hockey, earning NHL minutes in St. Louis, Montreal, Philadelphia, San Jose, and Dallas, playing in the AHL and IHL, and spending a year each in Germany and Russia. Late in his career, he kept a notebook of strategies.
In the autumn of 2005, he had retired as a player-coach with the UHL’s Missouri River Otters. He was once operating a part-time place of business activity at a metal corporate, providing personal hockey classes when Jeff Jackson (Lake Superior’s coach in ‘93) made him a volunteer assistant on his first Notre Dame staff.
“He had a brilliant mind for the game of hockey,” Jackson said, “and great communication skills. He was instrumental in helping develop the culture here.”
Four years as a college assistant (RPI, 2006-10), three years as a head coach and GM in the USHL (Dubuque, 2010-13) and five years leading a premier college program (Denver, 2013-18) honed a coaching style that has been hard to pin down.
“I try to take a little bit from everybody,” Montgomery said.
“It all has to fit with can we possess the puck and make plays when we have it, and two, how quickly can we get it back, so what are the pressure points? There’s some coaches that I’ve labored with that have nice concepts, however they don’t practice to the best way I imagine I need my workforce to play.
“So I don’t use it, but I try to learn and understand it so if I face it, I can beat it.”
Nearly three years ago, at a very public point, Montgomery turned to face himself, his family, and his friends. They’ve been battling together since.
That’s what he pondered that night in Philadelphia, when asked what it would be like to win it all.
“Well … since you’re young, that’s what you dream of,” he mentioned. “The more that I’m entrenched with the Bruins way of life, from the top all the way through our leadership core and every player, it feels like it would be extra special. And that’s because of the commitment and professionalism I’ve witnessed in a short time here.
“Then when you factor in what transpired three years ago, the growth I’ve had, it’s like — not for me personally, but repaying the people that stood by me. To be able to thank them for believing in me.”
If his day comes, the Cup would be filled with gratitude, enough to spill out of the bowl and down the silver sides. It would be a beautiful scene. It would be another day in the fight.
Matt Porter can also be reached at firstname.lastname@example.org. Follow him on Twitter: @mattyports.