Scenes From An Interview: Seven-Time Stanley Cup Winner Jimmy Devellano

A Life of Great Wisdom & Memories

By Gus Mollasis

In the 1967 Stanley Cup finals, the Toronto Maple Leafs beat the Montreal Canadiens, capturing their thirteenth Stanley Cup – the last time they would do so. When they won, a 24-year-old lifelong Maple Leafs fan Jimmy Devellano was on his way to forging what was an unlikely lifelong career in hockey starting as a scout for a 1967 expansion team, the St. Louis Blues.

Today, 51 years later, Detroit Red Wings Vice President Jimmy Devellano knows more than ever just how hard it is to win a Stanley Cup and he should. Jimmy D, as he is known in the hockey world, has been responsible for helping build seven teams that have won the coveted trophy, arguably the toughest championship to win in any sport.

As I sat in his downtown Sarasota condo, the sun shone and palm trees swayed on our picturesque Bayfront, but Jimmy D hardly noticed. The TV was on and it was tuned to a hockey game.

Sitting in his slice of paradise, he watches with keen interest as a goalie the Wings recently traded away is gunning for a win. “If Mrazek wins another game that improves our draft pick.” 

For Jimmy D, it’s always been about the draft, and in his opinion, NHL draft picks are the life’s blood of building a good team. His talent for team building has earned him a place in the Hockey Hall of Fame. It’s no accident that Jimmy D’s likeness in the Hall is in the builders category for crafting not one, but two dynasties in the National Hockey League – first with the New York Islanders, who won four straight Stanley Cups with Jimmy D being a part of three of them. 

“A great hockey team. Four straight Stanley Cups. A team that won 19 straight series before we got beat by the Oilers in 1984. I’ll tell you something, that will never happen again, a team winning 19 straight best of 4-out-of-7 series.”  

With success coming relatively quickly for the Islanders, from expansion team to Stanley Cup champion in eight years, a confident Devellano headed to Motown with a chance to help a “pizza man” named Mike Ilitch (founder of Little Caesar’s Pizza) build a winner.  

“I thought I could do the same thing when I arrived in Detroit and I promised that we could do it—win it all in about eight years.” 

It didn’t quite go according to plan. As early playoff exits mounted, everybody in the organization felt the heat and pressure to win, especially general manager Devellano.

Even with the legendary Scotty Bowman at the helm, the Wings couldn’t get past the hump and win the Cup. They were ousted in the first round by upstart San Jose in 1994, followed by a Stanley Cup sweep to the New Jersey Devils in 1995; and finally, a stinging defeat to the Colorado Avalanche in the 1996 Conference Finals that saw the Red Wings, a team that won a record 62 games, once again fall short. 

In 1997, a good part of the Stanley Cup solution came via a bold trade that landed Brendan Shanahan. But as the Red Wings were poised to win their first Stanley Cup in 42 years, the man who helped build the team into a perennial winner felt little joy. 

“That first Cup in Detroit was a sense of relief for me. When I went to Detroit from the Islanders, I promised everyone—the owner, fans and the media—that we would win a Cup in eight years. I felt we could duplicate the plan I used in New York to have an expansion team drinking from the Cup in eight years. My commitment, and one of the things I insisted on, was building the team through the draft, and I took heat for it at times when I wasn’t trading any draft picks.” 

“For you, a fan, winning the Cup was a great joy. For me, I was a happy, but more than anything I was relieved because I made a lot of promises and I wanted to keep my word.”  

Sadly, the celebration was short-lived, as six days after the Cup win, a limousine accident ended the career of Vladimir Konstantinov and severely injured Sergei Mnatsakanov, while another player, Viacheslav Fetisov, sustained minor injuries. Jimmy D remembers, “The joy was sucked out of the city, but fortunately we had five days to celebrate without knowing what would happen.”

“In 1998 we rallied as a team and repeated as champions while dedicating the season to both our fallen Wings, as we wanted to win it for both Sergei and Vladdie.” 

I asked Jimmy D about Vladdie’s condition some 21 years after the accident. “It’s relatively good news considering everything he went through. He’s alive, not in wheelchair, and he’s able to use a walker. You’re able to have short conversations with him and his memory is good. Vladdie is living with a wonderful family in Ann Arbor. I just saw him a couple of weeks ago at the premier of the film The Russian Five, which was phenomenal.” 

Jimmy D loves the game; that much is obvious. His place in it is legendary. When his mother was asked why Jimmy never married, she would smile and say because he is married to hockey.

The love affair started rather innocently and by accident. 

“How did I get to my first hockey game? My dad won tickets to the first hockey game I ever attended in 1956. I fell in love with the sport. It’s surreal. How the hell did you get to be general manager in the best hockey league in the world? I was a ninth-grade dropout and had a blue-collar upbringing with no sports background. How did I get here?” 

He wears his love of the game on his sleeve. “I loved going to the infamous Maple Leafs Garden. The white ice, the speed, the beautiful blue sweaters with the iconic Maple Leafs crest. And who would be there that night playing at my first game? Gordie Howe and the Detroit Red Wings. Who would know that at age 13, while I’m seeing my first live game, that someday I was going to manage that team? It was beautiful, just beautiful.” 

The story of how he got into hockey is just as improbable as winning seven Stanley Cups. 

“My parents ended up buying season tickets through my teen years. As I entered my twenties, I was working for the federal government and coaching minor hockey at night, going to Maple Leafs games and OHL junior games. I was a hockey nut. Then, in 1965, with an expansion announcement, the NHL doubled from 6 to 12 teams with teams in LA, San Francisco, Minnesota, Philadelphia, Pittsburgh and St. Louis.” 

“I don’t know why I decided I would only write to one general manager—Lynn Patrick of the St Louis Blues. Why did I pick him and St. Louis? If you’re looking to get into the game, wouldn’t you write all six? I can’t look you in the eye and tell you why I picked Mr. Patrick.” 

“Mr. Patrick, I go to all the games. I would like to scout for you for free in the Toronto area.”  

“Looking back, it was really no cost to me. I was going to these games anyway. He took me up on it and I started filing reports for him on junior players and NHL players. My own scouting reports. Scouting is the least glamorous job, but to me it was glamorous. He liked my reports, and after that year he put me on the staff and paid me. That was 51 years ago. And now, here I sit in Florida, 75 years old and still on the Red Wings payroll.” 

“You know what I’ve said in life. Generally, when you come out of nowhere, you need an angel and somebody to take a chance on you. I’ve tried to help a lot of people like that. But more often than not they are dreamers who don’t have the passion and the work ethic. They want it to be easy and you can pick that out real quick.”

“How did I get here? I don’t know; I guess it’s in my DNA. But what’s funny is that if you knew my parents, grandparents and my background, there was nothing that would indicate that Jimmy Devellano would become a hockey guy. They were not even close to being hockey fans. Not even close.”

As the sun continues to set on our talk, another playoff season begins and teams steady themselves for a run at the Cup. Jimmy D speaks from experience balanced by knowledge and is a bit haunted by the pressure of just how hard it is to win a Stanley Cup. His Sarasota perch would be a good spot take in one of those Stanley Cup parades that often take place in the winning team’s city. Just over the bridge on St. Armands, the owner of the Tampa Bay Lightning is building a mansion which could park 25 Zambonis and store a heck of lot of Stanley Cups…if he is fortunate enough to get there. Past St. Armands on Longboat Key is where Jimmy D was first introduced to the area by his friend and coach of his Islanders – an eight-time Stanley Cup champion, the late, great Al Arbor.    

2017: Hockey Hall of Fame, Stanley Cup 

Knowing what this man knows, I had to ask Jimmy an obvious question. “Jimmy D, how hard is it to win the Stanley Cup?” He smiles, actually winces a bit, as if he had one of those undisclosed injuries hockey players tend to hide during a Stanley Cup Playoff run.

“Pretty #@#@ing hard,” he says. “Really damn hard. There are 31 teams, and each year there is only one parade. If life was fair, then in a 31 or 32-team league, you’d win the Cup three times in a century. Look at Buffalo and St. Louis—never won a Stanley Cup yet.”

He doesn’t have to tell me that life isn’t fair; I’m a Detroit Lions fan.  

When Jimmy D arrived as the Red Wings’ general manager back in 1982, Little Caesar’s Pizza founder Mike Ilitch was hungry for a Stanley Cup and eager to fill his half-empty seats. He was giving away K-Cars at hockey games to boost attendance. Jimmy delivered big, and the Red Wings won four Cups under his watch. And while Jimmy is content winning seven Cups in his career, there was one chance to win the Cup in 2009 that got away – a stinging game seven loss to Pittsburgh that bothers him to this day.

“Yeah, that’s painful. There’s probably not a day that goes by that I don’t think about that series. But I had to let it go. There a lot of good hockey people who’ve never won a Cup. The best example is Emile Francis, a great hockey man, and it just didn’t happen. So, I’m super blessed.”

“Let me ask you as a fan. Can you imagine if we hadn’t won the Cup in 1997, 1998, 2002 and 2008 how bad not winning that one in 2009 would have felt then? For me personally, if I hadn’t been involved in those three Islanders Cups and the four Cups with the Wings, losing in 2009 would have been a terrible pain the rest of my career. I’ve been in hockey 51 years and to not have won a Cup would have been devastating.” 

The words hung there. I could not imagine that. His thought made us both pause. Me, the fan, asking the questions to the greatest architect of Cup winners, who, more often than not, has come up with the right answers making trades, draft picks and assessing talent on the ice. 

The hockey game on the tube is almost over.  

“We got eleven kicks at the can in the draft. Eleven picks that may help us get back to competing for a Stanley Cup. There are no guarantees. And it’s not easy. The fans have to be patient. Look at Toronto. They’re building, they’ve got some good players, but they’ve got no guarantees to get past Boston.”  

Who does he like to win this year’s Stanley Cup? He says that Tampa, under the guidance of General Manager Steve Yzerman, the Red Wings hero Jimmy D chose way back in the 1983 NHL draft, has a good shot at winning the Cup this year.

As I get ready to leave, I see that the hockey game has ended, and the ex-Red Wings goalie has notched another win, improving the Wings’ position in the June draft. As of this writing, the playoffs will be starting, and it is the second straight year that the Detroit Red Wings have missed the playoffs after making them for an incredible 25 years in a row. 

“I’ll tell you another thing that’s not going to happen. There won’t be another NHL team in this era who makes the playoffs for 25 straight years. In a lot of ways I’m most proud of that.” 

As I head out the door and into the fading sunlight, I am left with just one more question—one that I am afraid to ask after a couple of cloudy hockey years on The Road to Hockeytown (a shout-out to the 2008 book on Devellano’s life with the NHL).   

“Jimmy D. When do you think the Wings will win their next Stanley Cup?”

Jimmy D smiles, and, after a brief pause, shoots back a slap shot. “Maybe never,” he says. Forever the scout and sensing his words wounded this Wings fan, he adds, “Red Wings fans just have to be a little patient. In time, we’ll get there. The goal is to build a team that can compete for the Cup.”

Who would know this better than the man with seven Stanley Cups?