Her famous name and family ties have helped her organize and raise money. But in this too short PC leadership race her inexperience may be her undoing.

Oak 3 was a child rarely seen in public. She was assigned the codename at age 14, in 1988, by her RCMP security detail. She had a bedroom on the third floor of 24 Sussex, where she would wake up with her three brothers each morning, eat breakfast in the kitchen nook and leave for an international French school. She was once photographed on a tarmac greeting her father, codename Oak 1.

Caroline Mulroney has for the first time emerged in the public eye on her own terms, but she remains unusually unknown for a candidate trying to become premier of Ontario. As the Progressive Conservatives vote for a new leader on March 10, the daughter of former prime minister Brian Mulroney uses her surname for familiarity, but even this choice is ambiguous. “My legal name is Mulroney Lapham,” she says in an interview at a pub in Ottawa, “but politically, ‘Mulroney Lapham’ just didn’t work. Too much for a lawn sign.”

When asked why she didn’t run as Caroline Lapham, she says, “no matter what I do, people just always call me Caroline Mulroney.”

Her lawn signs spread her face in York-Simcoe, north of Toronto, where she launched her campaign as the Conservative candidate last summer, three weeks after buying a house in the riding. She is equally unfamiliar elsewhere in Canada, as a Serbian-speaking American dual citizen whose family is acquainted with the Trumps and who, in honour of her father-in-law who founded Harper’s Magazine, named one son Lewis Lapham III.

Dynastic politics is a rare asset in Canada, and Mulroney has received nearly $1 million in contributions, more than any of her opponents and more than Kathleen Wynne’s $715,000 in the last Liberal leadership race.

Mulroney’s political inexperience could’ve been a further advantage in a different Canadian election, but critics say, among her potential voters, she’s stuck between their fear of the premier and their fear of PC leadership rival Doug Ford; to guarantee neither, her would-be supporters may see the safer vote as Christine Elliott—because Mulroney is too unknown, not necessarily too soft.

“She’s certainly tougher than Ben,” says her brother, Mark Mulroney, referring to her other brother who hosts e-Talk. “People always try to say something about the toughness or whatnot, that she may not have that edge. The ironic part is that she does have that,” Mark says. “She runs even her charity board meetings like a corporate board.”

Mulroney, 43, is a philanthropic overachiever who had a legal career, had four kids, shuttled her sons to AAA hockey practice before her minivan became the campaign car, and with her sisters-in-law founded a women’s charity, The Shoebox Project for Shelters, through which she met Patrick Brown when he attended an event for the cause.

Her candidacy was not her father’s idea, but friends say he now can’t conceive of anything less than her premiership. Mulroney has more name recognition, more connections and more money than any other candidate, but the devil is in the lack detail known about her. She was born a somebody, but who?

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“No legacy of mine as prime minister,” wrote Brian Mulroney in a 1989 journal entry, “will ever come close to the magnificence of the children.” He and Mila had four, Caroline the eldest, born in Montreal while Brian was working at a law firm. She took her first communion during Brian’s 1983 Conservative leadership campaign, when he had no experience in public office.

“If parliamentary experience means that you lose the levers of government after only weeks in Parliament and after our party had spent 16 years in opposition,” he said on the campaign trail, “I’ll take my own experiences in the private sector, thank you very much.”

Living in the upper-class Westmount neighbourhood, Brian befriended his neighbour Jonathan Deitcher, who became a vice-president at RBC, and the Mulroneys sometimes stayed at Deitcher’s family house in Palm Beach, Florida. The house is a 300-metre walk from Mar-a-Lago.

“I’ve been going to Florida since I was a baby,” Caroline says. When she was 11, Donald Trump purchased Mar-a-Lago; her father got to know the future president, and Donald Trump Jr. and Ivanka Trump are three and seven years younger than Caroline. She says she has been to Mar-a-Lago once, invited to dinner by members of the club, and that she is not close with the Trumps. “I think the kids were more in the age of Ben and I,” says Mark. “We knew them peripherally. They were nice to us, but never invited to birthday parties or weddings or any of that stuff.”

Caroline was 10 when her father became prime minister, and he was paranoid for her safety, once fearing she and Mila had been kidnapped when he didn’t find them at home, forgetting it was a school day. The family was assigned Mounties, who first gave them the codenames Angel 1, Angel 2, Angel 3, 4, 5 and 6, Mark recalls, numbering the children in order of age (the youngest was Nicolas). They later became Alpha 1, Alpha 2, etc. until their father was re-elected. Mark says, “we went Alpha to Oak when he switched terms.”

Oak 3 as a teenager, Caroline recalls the Mounties stalking her through the mall with headset coils on their ears. “They were in suits, with the little curly things, at the Rideau Centre, and they’d be following me,” she says. “I probably didn’t date very much in high school because of it, but my Dad loved them.”

Philanthropy came with Caroline’s nature, and politics, with nurture. At the beginning of the AIDS awareness movement in the 1990s, she organized a volleyball tournament at 24 Sussex that raised $150,000 for the cause (at which Mila broke her ankle).

Caroline was among the most enthusiastic canvassers for candidate Alex Burney in the 1990 Ontario provincial election, and she read up on foreign policy before boarding a helicopter to visit George and Barbara Bush in Kennebunkport, Maine, where she planned to question the president on international affairs. He did in fact engage with the kids, even helping them fix the tennis ball machines.

Caroline got a media scare when Frank magazine published what Brian called “a scurrilous invitation to deflower my 16-year-old daughter.” The next year, Brian described her as “completely unaffected by the trappings of high office—but very sensitive to the attacks to which I am regularly subjected.”

Caroline studied at the Harvard Kennedy School. All the Mulroney children went to university in the U.S. In 2009, Brian told the Oliphant Commission that he used cash from lobbyist Karlheinz Schreiber to help pay for his children’s education. (The commission investigated the relationship between the former prime minister and Schreiber after Mulroney accepted cash from the German-Canadian businessman.)

At Harvard, Caroline perfected her Serbian, which was her mother’s mother tongue, and after her undergrad moved to New York City. She worked with Bear Sterns & Company, where she was put on projects in telecom investment banking and did a few merger and acquisition transactions, but what she wanted to do was go to law school, which she did at New York University. Studying for her bar exam, she once kicked out a student from her study group for lagging behind.

When she was working with the investment firm Morgan Stanley, a friend from Harvard set her up on a blind date at a pub with Andrew Lapham, son of the founder of Harper’s Magazine—“the famous Lewis Lapham,” as Caroline describes him.

Lapham was a Princeton graduate who also worked long hours in investment banking. They married in 2000 in Montreal and had their first children in New York City, including fraternal twins, then moved to Toronto to be closer to the rest of the Mulroneys.

“We annoyingly like each other a lot,” says Mark. “We’re surrounded by a very loving family, of which Caroline is the matriarch of the kids.” Caroline’s sister-in-law is Jessica Mulroney, a friend of Meghan Markle and fashion advisor to Sophie Gregoire-Trudeau.

One day near Christmas of 2011, Jessica suggested getting people to fill shoeboxes with gifts for women spending the holidays in shelters, Caroline told the Globe and Mail the next year. She and Jessica sent out a call to their girlfriends, and the idea spread such that The Shoebox Project for Shelters delivered more than 40,000 shoeboxes last year. In 2013, Lisa Raitt led an event for the charity at the Westin in Ottawa, where Caroline first met Patrick Brown.

“Patrick came to that event. He was excited about Shoebox,” Caroline recalls. “He wanted to help me in his riding, and so he helped organize a drive there. We already had a coordinator there, but he put together an event, so I got to know him there.” When asked if she ever heard rumours of him treating women inappropriately, she says, “No, I never did.”

Last year, Mulroney’s friend, Dan Nolan, asked her to be the MC for the Conservative leadership convention in May (Nolan was a senior aide to Brian Mulroney’s former finance minister Michael Wilson). Mulroney says of the convention request, “tThey were looking, I think, for someone to speak French.”

Soon afterward, Mulroney purchased a house in Georgina, Ont., that was transferred to her name on July 11, which was 22 days before she announced she would run as a candidate in the riding. Her family says she’d been talking about entering politics for about two years, but her father didn’t pressure her.

“My parents have this amazing ability that they have never once guided us toward any jobs,” says Mark. “I have never heard any commentary that Caroline really needs to do this.”

Brian is now bragging nonetheless. Friends have seen him this winter in Palm Beach, where he and Mila bought a $915,000, three-bedroom home in March 1997. (A neighbour says they have a Mini Cooper. In a 2012 dispute with neighbours who removed trees that served as a screen, their lawyer told a local reporter, “The only thing the Mulroneys want is their privacy.”)

In the new year, at a charity ball for a local zoo, friend Nancy Brinker says Brian raved about Caroline’s political debut. “He couldn’t wait to tell me,” Brinker says. “There was just a little twinkle moment of joy in his face to talk about his daughter.”

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In early February, Mila Mulroney was driving when Caroline called her with news, exciting enough to compromise her mother’s control of the vehicle. “Lady, you’re driving and swerving like a crazy person on the street,” said a police officer who pulled Mila over, as Caroline recalls. “What’s going on?”

Caroline had just told her mother of her leadership bid. She made the announcement on Feb. 4, three days after that of Christine Elliott. “It took me a little while to make my decision,” she says. Her husband became an executive adviser to Blackstone Group in Toronto in 2014, and their children are aged 10 to 13 (the youngest, Miranda, is nicknamed “Mini.”)

For her campaign vice-chair, Mulroney brought on board Derek Vanstone, former deputy chief of staff to Stephen Harper, and she has 30-50 volunteers working each day in her campaign office. Ben Mulroney helps her rehearse scripts. “I try to get advice from him on how to deliver certain lines,” she says. “For the convention, I had him read some of the things out so I could learn how to project my voice a little bit more like he does.”

The Shoebox Project partners with Shoppers Drug Mart, and “I spoke at a number of conventions, like for pharmacists and cosmetologists,” she says, “so I’ve done a lot of public speaking in my life.”

Mulroney has worked in the private sector over the past 20 years, and “generally speaking, ‘political experience’ is not highly valued in Canadian politics,” writes Paul Wilson, an associate professor of political management at Carleton University, in an e-mail. “I’ve been generally impressed by her campaign.”

Yet, critics say she comes off as entitled, a trait worsened by her father embracing his relationship with the American president. “His fawning over the Trumps is not a helpful thing for her,” says Peter Donolo, former communications director to prime minister Jean Chrétien. “The risk is she looks like a kind of Ivanka Mulroney.”

Donolo says the candidate would’ve been wise to keep her head down and run in a contested riding. “The higher the profile of the rookie [politician], the more the media is out to try to trip them up,” he says. “It’s not bad to get your sea legs while you’re new on the job, not to float on your name or your father’s network and to know why you’re running, to be able to articulate why you’re running. What are the two or things you really want to do?”

Mulroney has five: improve childcare (including adoption), restore trust in the party, lower taxes and oppose a carbon tax, help seniors by adding 15,000 more long-term care beds, and create jobs by expanding co-op programs and ensuring career councillors respect skilled trades. “The platform will have a small deficit,” she admitted in the first leadership debate.

“This girl is very, very qualified,” says Lucien Bouchard, for whom she helped campaign at age 13. Bouchard was a cabinet minister under her father until 1990. “I don’t think Brian is contemplating the possibility of a failure.”

Brian himself failed in his first leadership bid in 1976, and he spent the next seven years building a successful campaign. Caroline has had fewer than seven weeks to build hers, stopping in early March in Ottawa to speak to supporters, among them an 82-year-old retired engineer and a cow farmer.

“I have been sort of the more quiet Mulroney,” she tells them. “This is a wonderful homecoming for me to see so many old friends.” She recognizes faces from the childhood when she had alphanumeric codenames, and she tells them now, “I need you to make me your Number One.”

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