How Bruins Fan Living In Montreal Came To Boston’s Side Of Historic Rivalry

Montrealers are notorious Boston Bruins haters. It’s a heated, emotional rivalry that spans decades and generations.

Montreal, Quebec native Angelo Di Dio isn’t a typical Canadiens fan, instead, he holds his allegiance with Boston as a member of the Bruins fandom.

As Italian immigrants in Canada, Di Dio’s family was really into soccer into hockey, but he had a couple of uncles who jumped on the bandwagon in the 80s.

“It’s hard not to jump on the bandwagon if you look at those 80s Montreal teams,” Di Dio told NESN.com. “They were so dominant, of course after the Esposito-Orr era.”

When Di Dio was 11 years old, he began to truly understand the sport of hockey and used the famous 1988 Adams Division Finals between the Bruins and Canadiens to decide which team he would become a fan of.

Before the internet age, in 1988, the only way to get your sporting news in Montreal was on Hockey Night in Canada or in traditional newspapers. Di Dio, 46, remembers the Le Journal de Montreal hyping up the matchup and the history of the two teams and that the Bruins lost 18 straight playoff series to the Canadiens from 1946 to 1987.

“I decided whoever wins this playoff series, I’m going to cheer for,” Di Dio explained. “I get down on my knees, and I thank God every day that the Bruins won that series. I secretly wanted the Bruins to win. If I think back to that time, there was such an allure about that Boston team.

“Ray Bourque and Cam Neely, Reggie Lemelin and those big arrow flex pads that I had never seen before … so it was just everything about that team. They won that series and I just jumped on the bandwagon and never looked back.”

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Di Dio said he never identified with the Canadiens making it hard for him to even consider rooting for the Habs — even being in Montreal his whole life.

“I believe being a sports fan, you have to identify with the sports team, and I’ve always identified myself more like an underdog,” Di Dio said. “I identified myself as the hard-working underdog. The Bruins, to this day, they’re still considered hard-working. Even though they’ve been in the playoffs for so long now, there’s still that blue-collar identity to them, that root. Maybe because Boston is a blue-collar town. The Canadiens always had an elitist feel to them. Maybe because they won so much.”

Since the Canadiens are no longer the powerhouse that captured 24 Stanley Cup championships, Di Dio said it’s a bit easier to be a Bruins fan in Habs country.

“In high school and the early 2000s, when the Bruins started to dwindle again it was a little harder to be a fan (in Montreal),” Di Dio explained. “In the 90s it was easier because we had Andy Moog … he was a Habs killer.”

The tide really shifted in 2011 after the Bruins defeated the Canadiens in seven games. Di Dio explained he watched Game 7 at home by himself.

“It was April so it was still kind of chilly,” Di Dio explained. “All the lights were off, and I had my Bruins hoodie on, the hood over my head, and then by overtime, I had my Bruins blanket completely over me. I looked like a hermit in the house with no lights on, just the TV.

“When (Nathan) Horton scores that goal … I think my neighbors must have me from inside their house. It was it for me, even if they didn’t, I mean at that time I not thinking they’re gonna win the Cup. For me, that’s a skeleton key. At that point, I can do whatever I want in Montreal for the whole summer. I can wear whatever gear I want.”

He went on to explain that for many years, whenever the Bruins beat the Canadiens in the playoffs, it was his Stanley Cup.

“That’s all I needed. Even if they got swept in the next round, it didn’t matter. We had that over Montreal.”

The morning after the Bruins clinched their first championship since 1972, Di Dio was sitting on his front steps with the landscaping company doing work on his home when a scene similar from a famous movie broke out in front of him.

“I live on a street full of Habs fans,” he explained. “… All of my neighbors, walking by the house, look at me, nod their heads and say, ‘Congratulations.’ It was pretty special. It looked like a scene from ‘The Godfather.’ They were showing their respect. It was for that one day but it was like being a king.”

As a graphic designer, Di Dio spends much of his spare time creating content for the team he’s been rooting for since he was a little boy.

As the Bruins celebrate their centennial season, NESN debuted “Connection: A Century of Bruins Hockey” in late November. You can watch the special on demand anytime on NESN 360.