The political education of John A.D. Tory started early - very early.
"Even in the womb, [he]was involved in a political endeavour," said his father, John H. Tory, the recovering politician who nearly tumbled off the wagon and into the mayor's race this summer.
In 1979, John H.'s wife, Barbara Hackett, was pregnant with John A.D. while her husband managed federal Conservative Ron Atkey's successful campaign.
Mr. Atkey's wife was expecting too, so the couples squeezed in private birthing classes between kissing other people's babies.
As John A.D. and his siblings, Christopher, 28, Susan, 25, and George, 21, grew up, their father dragged them to rallies and door-knocking sprees, his idea of babysitting.
"I can't even tell you how many times we've been canvassing," John A.D. said.
"We're just natural-born canvassers," George added.
"It's the next Woody Harrelson movie. Natural-born canvassers. I'm going to get the round sunglasses," John A.D. said, laughing.
With such a head start, you'd think John A.D., 31, would be an established political figure by now.
Instead, he followed his lifelong dream and became a pilot - overcoming an eye injury after being struck by a fireplace poker when he was 14. His formal political career began just this year when he signed on to be an adviser to long-shot mayoral candidate Sarah Thomson.
The father of two, now the vice-president of operations for a private aircraft charter company, is thinking of running for office himself some day. If his work on the Thomson campaign is any guide, John A.D. has promise.
"He's got the answers in his blood. He's strong, he's vocal," Ms. Thomson said. "When you're talking around a table about what needs to be done, he's got no hesitation in saying, 'this is what I think.' "
John A.D., along with his youngest brother, George, have helped make the previously unknown businesswoman - whose qualifications for office amount to running a chain of gas stations, a slim magazine called The Women's Post and a losing bid for Hamilton council - a legitimate candidate in the 2010 election.
Although most polls have her running last, an Environics poll in June showed her in third place - ahead of Joe Pantalone, the deputy mayor, and Rocco Rossi, the former Liberal fundraiser and former CEO of the Heart and Stroke Foundation of Ontario.
Ms. Thomson can thank her gender and an endearing spunkiness for some of her success, but her biggest coup was a gutsy call for road tolls to pay for subway expansion.
Most advisers would have warned against tolling as political suicide; John A.D. encouraged her to go for it and aided her in shaping the proposal.
"He said to me, 'It's going to be a hard sell. It's a tax. The pros are, you're standing up and saying what needs to be done.' That's one of the things John's very good at," Ms. Thomson said.
"He's got really good political instincts," said Councillor Denzil Minnan-Wong, a long-time supporter of the elder John Tory. "For someone who doesn't deal with these municipal issues on a day-to-day basis, his ability to grasp complex issues is really impressive."
John A.D. and George came to the public's attention recently as their father reconsidered joining the Toronto mayor's race.
His indecision made life awkward for Ms. Thomson, who begged the elder Tory in an e-mail obtained by The Globe and Mail to stay out of the contest, in part so she wouldn't lose John A.D., who's been with her since January, and George, who joined the campaign in the summer.
"Going through the challenges together with John - or as we call him 'The Captain' - and sharing the ups and downs are memories I will treasure," Ms. Thomson wrote in the e-mail.
"John has put so much time into my campaign and his advice has proven extremely valuable. He truly knows his stuff and when I watched him speak at a fundraiser for me I realized how strong a leader he will be and how much he loves politics."
John A.D. barely knew Ms. Thomson when a mutual friend, Robert Perry, arranged a last-minute meeting for the pair at Barberian's steakhouse in January. They clicked. He agreed to advise her in a formal capacity, a first for him.
At that meeting, she certainly wouldn't have mistaken John A.D. for anyone other than his father's son. Both he and George look enough like their father to play younger versions of him in a movie.
George, who just graduated from Dalhousie University with a political science degree and is considering law school, has a tad more formal experience, having worked for provincial Progressive Conservative candidate Gary Grant in 2007.
Together they're jokesters. In an interview, they tease each other and crack wise about past campaigns - like how George scoped out an old Coffee Time as an office for Mr. Grant, a former senior police officer.
"We put a cop in a doughnut shop," he quipped.
But they turn serious when talking about the Thomson campaign, and watching their father endure political triumphs and heartbreaks.
"You don't necessarily like it when you watch somebody who you know and who you love and who you trust go up and really put [out]a message that is honest and genuine ... and then have people turn around and call some of those things into question," John A.D. said.
The family is tight-knit. John H. Tory gushes at the chance to praise his children, and John A.D.'s children, Isabel, 7 months, and John Michael, almost 3. (They call him Jack. "We wanted to give him a fighting chance," John A.D. joked.)
Yet when the putative mayoral candidate decided not to run, his children were among the last to know. And they didn't hear it from him.
Instead, Ms. Hackett e-mailed the four Tory progeny a heads-up 20 minutes before their father issued a late-night news release.
The Tory family had devised an internal communications strategy, so to speak, to avoid a quandary for John A.D. and George, given their volunteer work for Ms. Thomson.
Whatever his flaws, such an ethical approach is a hallmark of Mr. Tory's, one he seems to have passed on to his politically minded sons.
"When he started his re-decision," John A.D. said, "we all decided that the best thing would be for me to be not involved in his decision due to my involvement in Sarah's campaign. Everybody was fine with that."