Indeed, Elliott's grandfather is Chaucer Elliott, a member of the Hockey Hall of Fame, giving him an insider's perspective from the first days of his life. And Elliott, who has worked for the Toronto Sun since 1987, found a way to turn his initial privilege into a career based on earning people's trust.
Elliott is famous in Toronto for often disappearing during the first few innings of a game to contact his sources, and he's equally famous for filling his daily reports with exclusive information. But he wasn't always that keyed in, and he said his teachers would be shocked to learn of his success.
Elliott, in fact, recalled one teacher in particular -- a guidance counselor named Mr. Newman -- who tried to discourage the young man from pursuing his nascent dreams of becoming a writer.
"I said that I'd like to work at a newspaper. He's laughing, and he's looking at my marks," said Elliott, recalling an incident that took place more than four decades ago. "He said, 'You got a 61 in English composition and you got a 63 in English. You've got no chance.' I said, 'Sir, I've been working there for three years on weekends,' but he said, 'You can never work there full time.
"He said, 'Maybe you can get a job at the Napanee Beaver.' That's a bi-weekly [newspaper]. It's where Avril Lavigne is from, and it's like 20 miles away [from where I lived]. He would be shocked today. I went back to the reunion after 20 years, but I couldn't find him. Not that I was looking for him."
That story -- self-deprecating and vindictive -- is vintage Elliott, who delivers most of his asides in a laconic growl. Elliott even teased a few of his celebrated peers Saturday, taking shots at MLB.com's Marty Noble and Baseball America's Tracy Ringolsby during his question-and-answer session.
But his most interesting comments were reserved for what it meant to be a Canadian receiving one of the highest honors in America's National Pastime. Elliott, a long-time booster of Canadian baseball, said he finally realized the impact of his achievement from his nation's reaction to it.
Just a few days ago, Elliott received an e-mail from broadcast journalist Peter Mansbridge, whom he described as "Canada's Tom Brokaw." And months before that, he received a call from an even more prestigious man, validating a joke made by peer Marc Topkin of the Tampa Bay Times.
"I can remember at our meeting in Dallas, my phone went off and Marc Topkin yelled, 'It's the Prime Minister.' Everybody laughed," said Elliott. "A month later, I got a phone call. 'Yes, this is the Prime Minister's office. Could you please come down to the Royal York on Friday at 4:20?' I said, 'Who is this?' But I continued to talk to them, deduced that it wasn't a gag. And I was there at 3:30."
Elliott, a man and a symbol of national pride, is an unabashed patriot who wrote The Northern Game: Baseball The Canadian Way and has helped develop a website -- Canadian Baseball Network -- devoted to tracking the achievements of his baseball-playing countrymen.
But perhaps more importantly, he's been both an active inspiration and a guiding force in the lives of countless Canadian sportswriters who have sought his tutelage. Elliott has done things in his own iconoclastic way, but at root, he identifies as a Canadian and as a stranger in a strange land.
"I think as a nation we're as patriotic as you guys are, but we don't show it," said Elliott of his homeland. "Lester Pearson, the prime minister, used to say we had this inferiority complex. If you look at us too long, we get worried. And if you don't look at us enough, we get even more worried."
Now, Elliott is the heir to a legacy epitomized by the brilliance of Grantland Rice, Ring Lardner and Red Smith, fitting for a man who has done virtually everything in the game. Elliott began at the Ottawa Journal in the late '70s and he's thrived in this industry during changing times and changing expectations.
The veteran said that Andre Dawson and Robby Alomar were the best players he covered on a daily basis, and he used part of his speech to stump for a few players he deemed underrated.
Elliott lauded Jack Morris, Tim Raines and Larry Walker as deserving of enshrinement, and he said that the most memorable moment of his career was watching a team of unheralded Canadians defeat an especially star-studded edition of Team USA in the 2006 World Baseball Classic.
And that's all the icing on the cake of a career that almost never happened. Elliott said his mother was aghast when he first considered a full-time journalism career, but his father intervened.
"I had to meet two conditions: Graduate and never become like that writer who kept Ted Williams off his MVP ballot," he said of earning his father's acceptance. "The Expos had not even been born [and] the Blue Jays were not even a gleam in Paul Beeston's eye. No problem."
The 63-year-old -- a native of Kingston, Ontario, Canada's first capital -- began his acceptance speech in French on Saturday, and he said that this experience has brought his life full circle. Elliott can recall writing players and asking for autographs, and fellow 2012 inductee Ron Santo once replied.
Fast forward a few decades, and Elliott is still checking the mail and finding good news. The mustachioed veteran said Saturday that he has received congratulatory letters from iconic baseball men like Johnny Bench and Tommy Lasorda, a fate he never could have anticipated as a youngster.
It's all part of the Canadian dream for Elliott, but he's happy to share it with America. Elliott's big moment came Saturday, but the Hall will reconvene Sunday to induct Santo and Barry Larkin. Live coverage of the induction ceremonies on MLB Network and simulcast on MLB.com begin at 12:30 p.m. ET.
"I am a proud Canadian, but the thing is that my grandmother is from Madison, Wisconsin. I've never been to Madison," said Elliott. "But I've added up the days I've spent in America. I've now been in the U.S. for 8.5 years. If I'm here for another 34 years covering the game, then I can vote."