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As far as father-son trips go, Ken LeBlanc has his travel plans staked on what could be the granddaddy of them all in two years’ time.

PropertyGuys.com’s Ken Leblanc’s New Brunswick home houses his collection of Leafs memorabilia, including signed apparel from Auston Matthews and William Nylander.

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Already a die-hard fan of the Toronto Maple Leafs, the co-founder, president and chief executive officer of real-estate company PropertyGuys.com began a tradition last year of travelling from his native New Brunswick with his father, Gerry, to watch their beloved Leafs in the playoffs.

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The hook was that they would get tickets to a later round each year. So after attending Game 3 of last year’s first-round series against the top-seeded Washington Capitals – an overtime victory for the Buds – Mr. LeBlanc has ordered tickets for a game in the second round this time. The logic then follows that the pair will be going to the third round next year, followed by a trip to possibly see Toronto win it all in 2020.

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“We’re going to push it around every year until they make the Cup final,” he says. “So we’re going to go second round this year, third round next year and then the following year we’re going for the Cup.”

Ken LeBlanc began a tradition last year of travelling from his native New Brunswick with his father, Gerry, to watch their beloved Leafs in the playoffs.

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However, with the Stanley Cup drought in Canada’s biggest city sitting at 51 years and counting – the Leafs last hoisted the championship trophy in the spring of 1967 – Mr. LeBlanc knows that when it comes to sports, progress doesn’t always follow a straight line.

He is planning to do his part when it comes to boosting his team’s chances, though, even if that means letting the Leafs’ playoff fortunes dictate his sartorial style.

“Let’s just say when the Leafs win a game I’ll try to wear the same type of jersey for the next game or my lucky Babsocks,” he says, referring to a brand of socks featuring a caricature of the team’s head coach, Mike Babcock.

“Just kind of keep the flow going — I’m sure I influence those games quite a bit, you know,” he says, tongue in cheek.

With more than 100 franchises across Canada and celebrating its 20th anniversary this year, the success of PropertyGuys.com has also allowed Mr. LeBlanc to indulge his Leaf fanaticism in his home in Moncton.

He built a new house a couple of years ago, featuring a dedicated space in his basement to display his collection of Leafs memorabilia. Since Toronto returned to the National Hockey League playoffs last year largely on the strength of some of their young talent, Mr. LeBlanc decided to reflect that with purchases of signed apparel from the likes of twentysomethings Auston Matthews and William Nylander. He also picked up a 1954 rookie card of popular Leafs goaltender Johnny Bower, who passed away last December.

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“I’ve got myself a little mini Hockey Hall of Fame down there,” he says.

While he is excited for the start of the playoffs, he has no special plans for watching the games in this year’s run, which began yesterday. The Leafs play in Boston against the Bruins tonight. That’s because he gets “too emotionally attached” to the games and doesn’t want to be around his buddies – “I rather just try to contain that in my own home.”

His collection includes a 1954 rookie card of popular Leafs goaltender Johnny Bower, who passed away last December.

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In the Maritimes, Mr. LeBlanc says that the most popular teams are the Leafs, the Montreal Canadiens and Boston, which has Nova Scotia native Brad Marchand on its roster.

But the success of Nova Scotia’s favourite son, Sidney Crosby, has swayed much of the younger generation, he adds. In addition to scoring the golden goal for Team Canada in the 2010 Olympics, the Pittsburgh Penguins captain has three Stanley Cups on his résumé, including the last two in back-to-back years.

Even though he plays for a rival team, Mr. LeBlanc credits Mr. Crosby for coming back to the region every summer, where he holds an annual hockey school in his hometown of Cole Harbour. However, given that the Penguins and their superstar captain may be standing in the way of the Leafs if both teams get to the third round, there won’t be any divided loyalties in the LeBlanc household.

“I want Sid to do well but he already has a few Cups and I haven’t been around [to see] my Leafs win,” he says.

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Mr. LeBlanc does not have special plans for watching the playoffs because he gets “too emotionally attached” to the games and doesn’t want to be around his buddies.

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