Simpson talks glory years with Oilers, rise to Cup Final in Q&A with NHL.com

Craig Simpson is eager to begin his fourth Stanley Cup Final with the Edmonton Oilers, his first not on the team's payroll and first from high above the ice.

The 57-year-old will be in the "Hockey Night in Canada" booth at Amerant Bank Arena on Saturday, CBC and Sportsnet's analyst working with play-by-play announcer Chris Cuthbert for Game 1 between the Oilers and Florida Panthers (8 p.m. ET, ABC, ESPN+, SN, TVAS, CBC).

Simpson won the Stanley Cup as a member of the 1988 and 1990 Oilers, dual highlights of his 10-season NHL career. He then worked the 2006 Final as an assistant coach to Craig MacTavish, a heartbreaking seven-game loss to the Carolina Hurricanes.

The native of London, Ontario, a long-time resident of Edmonton, scored what ultimately was the Stanley Cup-clinching goal for the Oilers at Boston Garden on May 24, 1990, a 4-1 victory against the Boston Bruins in Game 5.

Simpson found another gear during the 1990 Stanley Cup Playoffs, at times struggling through a 29-goal regular season to score an NHL-leading 16 playoff goals, tied with Oilers captain Mark Messier for most points with 31.

His NHL career began in Pittsburgh, chosen No. 2 in the 1985 NHL Draft by the Pittsburgh Penguins out of Michigan State University. After 169 games with the Penguins through two-plus seasons, he was packaged in a seven-player trade that sent future Hockey Hall of Fame defenseman Paul Coffey to Pittsburgh on Nov. 24, 1987.

Six months later, at age 21, Simpson was a Stanley Cup champion.

Hockey Night in Canada analyst Craig Simpson (right) with play-by-play announcer Chris Cuthbert before Game 3 of the 2024 Western Conference Second Round between the Edmonton Oilers and Vancouver Canucks at Rogers Place in Edmonton.

Simpson had 497 points (247 goals, 250 assists) in 634 regular-season games, playing his final 46 for the Buffalo Sabres. At 6-foot-2, 195 pounds, he would park himself in front of opposing goalies so solidly that he sometimes wore a flak jacket to protect his back from the crosscheck pounding he would absorb from defensemen.

On Tuesday, thoroughly researched for the Final as he prepared to head to Sunrise, Florida, Simpson spoke with NHL.com from Edmonton, happily considering that for all his time on the road, he'll have two and perhaps three "home games" to call in the days ahead.

How much are you looking forward to one day -- maybe this month -- losing the title of being the most recent Edmonton Oilers player to score a Stanley Cup-clinching goal?

"I think it would be a great honor to watch somebody else hold that title for a while. It's amazing how quickly time flies. In some ways, 1990 feels like yesterday. In other ways, it was eons ago. I feel a lot of pride having been a part of those two championship teams (1988, 1990) … my first one was Wayne Gretzky's last year in Edmonton, then Mark Messier led us as captain in 1990."

The Oilers were within one win of the Stanley Cup in 2006, playing 24 games that postseason. Take us back there, and your view as an assistant coach?

"My experience as one of Craig MacTavish's assistants was just a great reminder of how devastating it is to lose. I've never felt in my hockey world that hard a disappointment. Our guys played so hard, so well, they accomplished so much. And not unlike Edmonton and Florida now, they grew so much during the playoffs.

"Our 2006 team was such a better team by the Stanley Cup Final than they were in Game 1 of the first round against the Detroit Red Wings (a 3-2 double-overtime loss). To see those guys play so hard and to get nothing out of it, to lose (3-1) in Game 7… it really stands out to me how precious it is to get to the Final and how fortunate you are to be able to go on the journey and win -- or just how devastating it can be to lose.

"Our guys gave everything they had, just as the Hurricanes did, but Carolina is celebrating in their dressing room and we're hanging our heads; we can't believe it's all over."

Craig Simpson during a 1990-91 game with the Edmonton Oilers. He had won his second Stanley Cup championship with the team the previous season.

It's been 31 years since a team based in Canada -- the Montreal Canadiens in 1993 -- won the Stanley Cup. No cheering from the broadcast booth, of course, but you have a history with the Oilers. What would it mean in Edmonton for the Oilers to go all the way?

"I was traded here from Pittsburgh in November of 1987, and I've basically lived here ever since. It's very much my community, I had a charity event here for 35 years. From a community standpoint, being around here, I know how much the Oilers mean to the fans.

"Going back to 2006, just the spark of enthusiasm back then, how loud the building was, it was unlike anything I had experienced as a player in 1988 or 1990. Not that the fans weren't into it back then, but to go from 1990 to 2006, you know how hungry the fans were for success.

"The way they support the club, the way the Oilers are part of everyday life, you go into a school and the kids are talking about the team and hockey. I'm sure a guy like Connor McDavid, just like it was for Wayne, walks around city and has people constantly coming up to him, so passionate about the game.

"I'd just be thrilled for the fans to embrace a championship, to feel that again. You've got a whole new generation of fans. So many of them didn't watch us in 1990, now suddenly this is their team, their players, their heroes. I think that would be just amazing."

Edmonton called itself "City of Champions" during the Oilers' 1980s dynasty run, the Canadian Football League team (the then-Edmonton Eskimos) winning four Grey Cup titles that decade as well. The downtown area has undergone a transformation -- a renaissance, in a way -- with Rogers Place and an Oilers fan base probably never more engaged …

"Look at (Oilers owner) Daryl Katz and OEG Inc. (formerly Oilers Entertainment Group), the investment they've made in that downtown core with the mindset of 'Can you build a championship team?' They've changed the footprint of our downtown.

"Every game, there are watch parties, the Moss Pit (where fans gather outside Rogers Place on game nights; Ice District Plaza unofficially renamed for hugely popular late dressing room assistant Joey Moss) … that kind of commitment to the team, making sure the team has everything, I'd feel very special for Daryl.

"We went through some rocky times with our ownership, almost lost the team, and now to see what the downtown core looks like now with what I think is the best arena in the League…

"The alumni group have done a great job of bringing former players in to interact with today's players. Everyone who's been a part of a championship team always holds that. It's the franchise that gave you the opportunity to live out your dream as a player. It would be thrilling for this generation of Oilers to feel that as well."

Craig Simpson carries the puck for the Edmonton Oilers during the 1991 Stanley Cup Playoffs.

There's been a very real growth and maturation process this season with Connor McDavid and Leon Draisaitl …

"I've loved watching the way they've been able to mature and now realistically can talk about wanting to win. It's not farfetched, obviously even more when you're four wins away.

"I think the team has realized maybe their shortcomings in the past, that you couldn't really have an honest conversation about winning the Stanley Cup. What I've loved watching this year has been how that has grown, how comfortable they are now to be able to talk like that. They know they do have that kind of team and bond.

"What's failed this group in the past is that they haven't been able to consistently defend. As much as you say what great teams the Oilers of 1988 and 1990 were, we had to learn that as well. That's what's been brilliant this year.

"Look at their three-game winning streak to eliminate [the Dallas Stars] in the (Western Conference Final). They've won seven one-goal games [these] playoffs (one in overtime, another in double-overtime). That's what allows those top leaders to really believe. 'We now get it, we know how to play, how to react…' That's been pretty special to watch, the growth that they've had."

A 2-9-1 start to the season didn't exactly get the Oilers season off to a good start. What do you make of how they turned things around?

"I think it's the journey, of a season that started with great expectation. I'm sure they thought, 'We should be a Stanley Cup contender, we have two of the best players in the world,' then to basically get stripped down bare in that first month of the season. Sometimes you need to have that vulnerability with each other. That's the big intangible on great teams.

"Everyone talks about respectability, responsibility, accountability … to me, it's vulnerability within your group. I loved that one moment with Connor and Leon on the bench when they tapped each other on the leg. They were staring off like, 'I can't believe how bad this is, but we'll be OK.'

"I couple that with the other night, at the end of the series against Dallas, when everyone is leaving the ice after the presentation of the Clarence S. Campbell Bowl… that's the full-circle journey, that's the season. I thought about the rawness of nothing going right and everything being exposed, having had such a terrible start but these guys still believing they were a good team, that they were good players."

Craig Simpson of the Edmonton Oilers and Eddie Olczyk of the Winnipeg Jets chat during the 2016 Tim Hortons Heritage Classic Alumni Game at Investors Group Field in Winnipeg on Oct. 22, 2016.

About that start: Glen Sather, architect of those great 1980s Oilers teams, used to say, 'You think it can't get any worse? You're wrong, because it can.' How much truth is there in that?

"It's a good saying because guys can wallow in bad things happening, but you can't feel sorry for yourself. You need to turn it around. You need to do something dramatic to make that change.

"I credit Jeff Jackson, who came in last August (as CEO of Oilers hockey operations), and (general manager) Kenny Holland for making the call this season to change coaches (replacing Jay Woodcroft at 3-9-1 with Kris Knoblauch, who went 46-18-5). That's not an easy one but they needed a change, a little bit of a reset.

"Part of that journey, being exposed so badly so early, has built them up to understand what it takes to get through it. They've brought themselves back and they realize, 'Man, when we play like this, we can start talking about being Stanley Cup champs. We have the depth and the ability.' That's an amazing part of what this season has been like for them."

There might not be such a thing as destiny in hockey, but strange, unexplainable things can and have happened. Is that even a bit of the story for these Oilers?

"There are magical runs, no question that's an element. Belief is a strong thing. I remember that in 1993 with the Canadiens. 'They're winning another overtime game?' That's insane. Sixteen wins and you get 10 of them in the extra frame? That's probably never going to happen again, I can't imagine it.

"My first experience winning the Stanley Cup was so surreal. I was 21, from 2 1/2 years in Pittsburgh, no playoffs, getting to my first postseason in the NHL with the best team in the League, the best player with Wayne. We went 16-2. Sheepishly, I didn't think there was any point during that experience that we weren't going to win the Stanley Cup. That's how good that group was.

"The journey in 1990 was a different one. We're climbing back to that level again with a lot of new faces who are bringing a lot of energy."

Craig Simpson (back row, second from left, arm raised) celebrates with Edmonton Oilers teammates following the team's 1988 Stanley Cup victory.

You speak about Connor McDavid not being able to set foot in Edmonton without being recognized. You were one of the heroes of the most recent Oilers championship. Thirty-four years later, are you still stopped by fans on the street?

"I am in Edmonton. People are so respectful. None of the younger kids know my era of players but when you've been a part of Stanley Cup championships, people are quick to say, 'Hey, I loved watching you guys play back then, it was a lot of fun, now my kids are hockey fans.'

"That's the special thing that every player will tell you about being part of a championship team. The city embraces you, but it's also about your embrace of your teammates. It doesn't matter how long you go between seeing each other. You exchange text messages… you live with that the rest of your life."

Top photo: Craig Simpson of the Edmonton Oilers celebrating with the Stanley Cup following his team's Game 5 championship-clinching win against the Bruins in Boston on May 24, 1990. Simpson scored what would be the Cup-clinching goal in the Oilers' 4-1 victory.