From his days playing for OMHA minor hockey teams in his native Kingston, through a 20-year Hall of Fame career and on into his tenure as Kingston Frontenacs GM, Gilmour has seen that success doesn’t move in a straight line. The revered Toronto Maple Leafs great knows that work ethic can’t be measured.

“Try to get better each and every year,” says Gilmour, now in his third year as Frontenacs GM. “Sometimes you see kids who are kind of all-stars at nine, 10 years old but who might have been early bloomers. You got to be given the opportunity to get better with teams, camps and schools, but it’s still up to the kid. 

“When we draft into junior at age 15, sometimes when we get past the fourth or fifth round we’re looking at those guys to come in as 17 or 18-year-olds. It’s projection. 

“There’s going to be small guys, there’s going to be the big guys,” adds Gilmour, who recalls being a 142-pound rookie in 1980-81 with the Cornwall Royals, whom he helped capture the Memorial Cup. “You have to find your niche. When I put my equipment on, I didn’t feel small. In my eyes I was, but that’s not how I played.”

Gilmour’s minor hockey experience might look very alien to children and parents today. He recalls having to help resurface the ice after some games at the Cook Brothers arena in north-end Kingston; boys could also play house league and rep at the same time. He also built bonds that endure to this day.

“With me being back in Kingston, you always see guys you played against,” Gilmour says. “One person who stands out is probably Ian MacInnis, who’s the coach, GM and owner of Cornwall [Colts in the Central Canada Hockey League]. We played together and then he was on my line [with the Royals]. We talk all the time when I’m trying to find out about a player. 

“We also had the rivalries,” Gilmour adds, rhyming off a few well-recalled juniors of his vintage. “Belleville had Steve Molaski, who I later played with in Cornwall. Trenton had [future Edmonton Oilers maintain] Steve Smith. In Oshawa, there was Dale Hawerchuk, Dale DeGray and Peter Sidorkiewicz [all later coaches or GMs in the OHL]. In Peterborough, there was Doug Evans.”

Gilmour’s career included a Memorial Cup in junior, a classic Canada Cup triumph in 1987 in the last great Cold War showdown and a Stanley Cup two years hence with Calgary Flames. Raising the silver mug in ’89 was a signature moment.

“When you look back at it, winning the Stanley Cup was pretty unique,” he says. “I don’t think there’s one hockey player who, when you make the NHL, thinks about the Hall of Fame. That’s never on your mind until your career is over. That was a great honour.”

Gilmour took the Frontenacs’ coaching reins in 2008-09. After three seasons, he became GM, with former Leafs teammate Todd Gill going behind the bench. Having assembled a strong young nucleus, Gilmour relishes the endless tinkering that it takes to get into OHL contention.

“It’s a chess match. There’s a lot of work to be done with projection. I’m lucky because I have a great scouting crew and I have [assistant GM] Darren Keily helping me. It’s a good working relationship.”

That role has led to speculation about whether Gilmour might return to the NHL in a front-office role, but the Hall of Famer believes he’s best suited to where he is.

“Your time’s so occupied between your family and kids,” Gilmour says. “When the season’s over, if anyone communicates with you, obviously you’d think about it, but I’m not doing so at this time.”