They played together on the Calgary Flames team that won the Stanley Cup in 1989, were briefly teammates in Toronto with the Leafs, and have remained active in the game since their playing careers ended.
So it seems somehow fitting that Doug Gilmour and Joe Nieuwendyk will once again come together, this time as inductees into the Hockey Hall of Fame.
The induction ceremony will take place on Monday in Toronto as the Hall will also open its doors to goaltender Ed Belfour and defenceman Mark Howe, who will join his father Gordie as an honoured member.
"He was a great teammate, a character. Not much really bothered Dougie," said Nieuwendyk, who is general manager of the Dallas Stars, one of the NHL's top teams so far this season.
"He very much liked to have a good time off the ice in the locker room joking around. He didn't take it too seriously but when the puck dropped he turned into this ferocious 170-pound guy."
For Gilmour, a former Leaf and Chicago Blackhawks captain, the Hall of Fame tribute is another in a long list of hockey accomplishments for the scrawny Kingston, Ont., kid who many figured would never amount to much in the game.
At 5 feet 10 inches and 175 pounds, Gilmour went undrafted in his first year of NHL eligibility.
Even after he piled up 119 points in his final junior year with the Ontario Hockey League's Cornwall Royals in 1981-82, Gilmour had to wait until the seventh round before the St. Louis Blues called his name.
And despite totalling 128 goals and 203 assists in 186 games during his junior career, Blues coach Jacques Demers took one look at the undersized centre in training camp and asked one question.
"Demers asked if I could check," Gilmour recalled. "I said, 'Well, yeah.' You do what you can to stay there [in the NHL]"
And stay he did, a memorable career that spanned 20 years with seven different clubs in which he scored 450 goals and 964 assists in 1,474 regular season games.
It was in the post season where Gilmour cemented his reputation as a clutch performer, tallying another 188 playoff points (60 goals, 128 assists) in 182 games.
When the Flames were knocked out in the second round of the playoffs in 1988 after finishing first overall during the regular season, former Calgary GM Cliff Fletcher knew that changes had to be made.
He targeted Gilmour and the following season he landed Gilmour along with Mark Hunter, Steve Bozek and Michael Dark from the Blues in exchange for Mike Bullard, Craig Coxe and Tim Corkery.
Playing for the first time with Nieuwendyk, Gilmour helped lead a veteran-laden Calgary squad to its first – and to date only – Stanley Cup championship in 1989.
Fletcher will tell you that the Flames would never have won that year if not for Gilmour.
Fletcher moved to the Maple Leafs in the summer of 1991 and on Jan. 2, 1992, he brought Gilmour on board in a blockbuster deal involving 10 players, the largest trade in league history.
The Leafs missed the playoffs that year but then began a memorable run that saw Toronto advance to the Eastern Conference finals in 1993 and 1994.
During the 1993 playoff run, Gilmour scored one of the most memorable goals in Leafs history in Game 1 of the conference semi-finals against the Blues.
Gilmour negotiated a 360-degree spin move behind the St. Louis net before he jammed home a backhander past Curtis Joseph that won it for the Leafs in the second overtime period.
Gilmour said another thing he'll never forget about his tenure in Toronto was when the Leafs came close to landing Wayne Gretzky during the summer of 1996.
Gretzky was a free agent looking to sign a contract that would be his last as a player and he had targeted Toronto as his first choice.
Gilmour said he took a phone call from Fletcher that summer asking him a simple question.
"Cliff said, 'How would you like to have Gretz?'" Gilmour said. "I said, 'Are you kidding me? I'll play wing right now.' I said he can have the C."
The deal was nixed at the last moment by former Leaf owner Steve Stavro and Gretzky wound up signing with the New York Rangers.
Gilmour was traded that season to the New Jersey Devils and he would bounce around with the Devils, the Blackhawks, the Buffalo Sabres and the Montreal Canadiens before returning to the Leafs in 2003.
In his first game upon his return Gilmour injured his knee that would send him into retirement.
Gilmour is currently the general manager of the OHL's Kingston Frontenacs.
With reports from David Shoalts