The then-Tor GM was sending fan favourite Wendel Clark, along with Sylvain Lefebvre, Landon Wilson and a first-round pick to the Quebec Nordiques for Mats Sundin, Garth Butcher, Todd Warriner and a first-round pick.
It was June 28, 1994 - draft day in Hartford.
More than 12 years later, Sundin finds himself three goals shy of the 500 club for his career - 362 of them wearing the Leafs uniform.
"He's one of the best athletes that I've had the pleasure of coaching," former Leafs coach Pat Quinn said Wednesday from Vancouver. "But I think I remember less about his goal-scoring and more about his leadership and his high level of play on a consistent basis. I guess in the end that's why he's scored so many goals and so many points."
Leaf fans have Fletcher to thank.
"Naturally I'm very proud of the trade for how Toronto has benefitted from it and how Mats has led them for more than a decade," Fletcher said. "And the good news for Leaf fans, at least from my perspective, is that Mats still has a lot of good years left in him. He is their leader and will continue to be."
But making the trade still wasn't easy.
"I mean, I had a great relationship with Wendel and he was a heart-and-soul player," Fletcher said. "Any time you trade a heart-and-soul player, it's an emotional transaction, and particularly in this case someone that meant so much to the Leafs franchise. He was sort of their bastion of hope for so many years when the team wasn't doing very well.
"It was a very difficult trade to make but from the hockey point of view it was one that if you were responsible for making the decisions for Toronto, it's one you had to do."
Fletcher had to do the deal, because he couldn't pass up what was coming the other way: A six-foot-five, 230-pound Swedish stud with hands of gold. And only 23 at the time.
"He had had a couple of tremendous years in Quebec already when we made the trade for him," Fletcher recalled. "He was big and strong and durable and so talented. Even back then I thought he would have another 15 years ahead of him. I guess it worked out.
"Even better was that we were able to bring Wendel back to finish his career in Toronto."
Sundin admits he didn't know at the time what he was walking into after being the guy traded for Wendel.
"I don't think I realized, really, the effect that Wendel had on Toronto, his popularity here," Sundin said Wednesday after practice. "At least not until I came here the first day and met the media and the reaction from the fans."
But he's certainly glad Fletcher pulled the trigger.
"It changed my career into the right direction," said Sundin. "Becoming a Maple Leaf has really helped me develop my game on and off the ice, learning about leadership. I have a lot to thank Cliff Fletcher for."
The 35-year-old native of Bromma, Sweden, insists he's not too preoccupied with the 500-goal milestone.
"Right now the only thing on my mind is the next practice, the next game. It's one of those things that once my career is over I'll appreciate it more."
But he laughed when asked what his response would have been back in June 1989 at the age of 18, moments after being picked first overall by the Nordiques, if a reporter would have asked him whether he'd score 500 goals in the NHL.
"Not a chance, probably," Sundin said with a chuckle. "Your first year in the league, you're thinking to yourself that you're hoping to play three or four years in the league. (Scoring 500 goals) is something that I would have never dreamt about."
A hat trick Thursday at New Jersey would do it. His fans no doubt hope it comes Saturday at home to Calgary.
"As long as it's in a game we win, that's the only thing I care about," said Sundin, who has one goal and three assists in four games this season.
Quinn coached Sundin for seven seasons in Toronto and was most impressed with the captain's consistency.
"Skill guys don't always play at a consistent level and I think as a coach you want to have that trust that you can put that person out in a certain situation and you feel like the job is going to get accomplished and that's Mats," said Quinn.
Leaf fans can also thank then-rookie Nordiques GM Pierre Lacroix, who had just replaced Pierre Page a month earlier before completing the blockbuster with Toronto.
"They had a lot of young, talented players at that time but felt someone like Wendel Clark could be a difference-maker for them in that he brought a tremendous physical element to the game," said Fletcher.
From the Leafs' perspective, a loss in the conference final to Vancouver in '94 left them wanting to make a move.
"We had just come off two years in a row reaching the conference finals but we weren't very happy," said Fletcher. "The second year we lost to Vancouver in five games and we'd been substantially outplayed. At that time all of us involved in the decision-making process felt to acquire a big centreman like Mats would really ensure the long-term competitiveness of the team."
Unfortunately for Sundin, he arrived just as the team began to fade for a few years. He also had the unenviable task of not only replacing Clark but eventually Doug Gilmour as well. It took several years before Toronto hockey fans warmed up to Sundin the same way they did for those two icons.
"It's probably that mentality in the Toronto market that Europeans maybe couldn't be raised at the same level as some of our Canadian kids," said Quinn. "As far as I'm concerned, I know he's a proud Swede but you'd never know he was any different than the rest of us. He cares about his teammates, he's got all the values that we as Canadians love in players. It took a while but I think that's why people (in Toronto) have found out he's the real deal."
Fletcher also wished Toronto fans had embraced Sundin a little more quickly.
"It bothered me to some degree that it took a long time to finally receive the recognition he was due a lot earlier," Fletcher said. "But it has evolved and I'm just happy for him and the great career he's had. I'm sure he's looking for that elusive thing he hasn't won - the Stanley Cup. But he has a number of years left in his career and hopefully he'll find that some day."
Sundin, who has an option year for next season on his current contract, did lead the Leafs to the 1999 and 2002 conference finals, but never a Cup final berth. Perhaps it's because he wears the unlucky 13 on the back of his jersey.
"I grew up wearing 13 as a kid, then had 19 as a junior player," said Sundin. "When I came over to the Quebec Nordiques, Joe Sakic had 19 so I had no choice, I went back to my old number. It's supposed to bad luck but so far it's been good to me."