He's 77 now and is a part-time scout for the team. "Training camp was a lot different in my day because we came to camp to get into shape and they come to camp in shape," says the last man to captain the Leafs to the NHL championship - way back in 1967.
He'd sure love to see the drought end.
"I can't say we're going to win the Stanley Cup but you can always hope," he says. "Stranger things have happened."
Leafs fans will hope that free-agent pickup Jason Blake repeats the 40-goal season he had with the New York Islanders, and that rookies such as Jiri Tlusty emerge to challenge for positions.
"It was nice to get out there with the guys," Blake said after his first practice with his new teammates. "It was a good skate."
Mats Sundin is the only Leaf to score 40 goals in a season in the last 10 years. He got 41 in 1997 and again in 2002. Lately, the team has craved a top gunner. So, the arrival of Blake is an important development. He'll likely play on a line with Sundin, too, which potentially gives Toronto the big-impact unit up front that it has lacked.
"Hopefully, it happens," said Blake. "Chemistry is a big deal with linemates and I'm sure we won't have a problem with that.
"I've played against Mats for years and the one thing that impresses me is that he's so big and strong. I probably got under his skin a few teams. If I get a chance to play with him, it'd be a great opportunity."
Blake got a US$20-million, five-year contract from the Leafs, but he insists he doesn't feel any added pressure to produce goals because of it.
"It's the same game, the same puck," said the 34-year-old Minnesotan. "It's a new beginning for me.
"I'm just trying to embrace it. I'm excited to be here."
He wants to be a complete two-way player and not just a shooter, he said.
"Everybody wants me to score but everything starts from the defensive zone on up," he said. "Hopefully, I can get better at it each day."
Tlusty also hopes to get better each day. The 19-year-old Czech was Toronto's first pick, 13th overall, in the 2006 entry draft and he spent most of last season being coached by former NHL defenceman Craig Hartsburg with the OHL's Sault Ste. Marie Greyhounds.
"He helped me so much," said Tlusty. "I learned lots of new things about North American hockey and life. It was a good year for me."
He couldn't speak English at camp a year ago.
"I just sit in dressing room looking around without talking," he recalled. "It was hard for me.
"Now I can speak with somebody. I feel more comfortable."
Fellow-Czech Tomas Kaberle has taken Tlusty under his wing.
"We are from same town," said Tlusty. "I feel better if he's here.
"It's good for me. I have to sometimes talk to him in Czech language."
More than 50 pros are split into three groups for 90-minute sessions on Ricoh Coliseum ice and head coach Paul Maurice blows his whistle while GM John Ferguson and assistants including Doug Gilmour assess the talent with watchful eyes.
Equipment dealers set up their wares on tables and Andrew Raycroft tries out some new goalie sticks while Alexei Ponikarovsky samples helmets.
Ricoh Coliseum staff wheel in carts of bagels and jugs of juices. The arena on the CNE's lakeshore grounds is brrrr, cold.
Armstrong reappears in a downstairs corridor and munches on a muffin. Some of the Leafs he'd been watching have been in skates for weeks. When he was a young pro, he couldn't skate before camp because artificial ice was rare.
"We never even got on the ice in summer time," he said. "And somebody tries to say hockey was better then than it is now? Crazy, eh?"
Players didn't make the big money shovelled out now so Armstrong worked surface jobs at a Sudbury region mine during his first 10 years in the NHL.
Time marches on.
"I love going to games," he says of his task of scouring OHL cities for prospects and reconnecting with former teammates and opponents. "I see lots of old-time hockey players, and the older we get the better we were."
Blake's expression turns serious when he's asked to predict the outcome of Toronto's season.
"It all started today," he replied. "No one said we're going to win the Stanley Cup.
"The biggest thing is that we want to compete for the Stanley Cup on a nightly basis. The season is so long. Some teams start off great but maybe don't play great around Christmas time. We want to compete every night. If we can do that, I'm not saying how far this team can go but I like our chances.
"I wasn't here last year but you can sense disappointment about last year. Guys are excited. There's a good vibe in the room and around the guys. I'm not one to make predictions but as long as we're competing on a nightly basis we should do alright."
There's always hope.