Chrystia Freeland stopped next to me at a red light. I was on my bike and asked, ‘Aren’t you supposed to be in Washington?’ She answered, ‘I’m heading back this afternoon.’ It was a brief encounter that was both endearing and bewildering. — Joe o’Connor,

WHAT MAKES CANADA’S SECOND-MOST RECOGNIZABLE POLITICIAN TICK? BY JOE O’CONNOR

Don Freeland, a retired lawyer and farmer with a 6,000-acre spread in Peace River, northwestern Alberta, was in the cab of his combine Tuesday afternoon, hurrying to bring in the barley harvest before the bad weather hit. It has been a cold, damp September out West, Freeland said, and farmers just have to deal with it. Besides, there are much more irksome issues than the weather, including the “dirty rotten dairy monopoly that every political party panders to and that should be disbanded altogether — in my opinion.”

Freeland has other opinions, including of his eldest daughter, Chrystia. Better known as Canada’s Foreign Affairs Minister and the trade representative U.S. President Donald Trump declared, and not via a tweet, that he did not “like” during the end days of the tense 14-month negotiation that produced the United States-Mexico-Canada Agreement (USMCA) — a deal that, among other things, gave American dairy farmers a cow’s udder more access to Canadian markets.

“I think it’s a good deal for Canada — and it had to happen,” Don said. “Canada didn’t have much choice, eh? And remember: Chrystia is not the boss.”

Freeland may not be the boss, but she is arguably the country’s most recognizable politician next to her boss, the Prime Minister. She’s by all accounts a phenomenon, a whirlwind who went from being a journalist/public intellectual, who asked a bunch of good questions and wrote some lofty books, to being the face of a trade deal that could define the country’s financial welfare for the next generation, for better or worse.

On the Monday morning before the new deal was struck, when the outcome was still very much uncertain, and fears of a calamitous end were gnawing away at Canadian negotiators, Freeland went for a run near her midtown Toronto home. It was around 9:45 a.m. She was dressed in a white Tshirt and grey shorts. Her hair was tied back from her face and she was moving at a reasonable clip, with no visible security detail.

None of the passersby in the area appeared to recognize her or, if they did, they didn’t care. Freeland looked, if there is such a look, pretty much like your typical middle-aged mom, with two daughters (Natalka, Halyna), a son (Ivan) and a husband (New York Times reporter, Graham Bowley) at home, a headache of a to-do list, and a desire to clear her mind before getting back down to it.

Freeland stopped next to me at a red light on Yonge Street. I was on my bike and asked, “Aren’t you supposed to be in Washington?” She answered, “I’m heading back this afternoon.” It was a brief encounter that was both endearing and bewildering. Endearing because whatever massive stress Freeland was under, the 50-year-old appeared unflappably calm; and bewildering because despite the massive stress she was under, it was 9:45 a.m. and she wasn’t in an office, somewhere, preparing for the next round in the NAFTA fight.

Part of Freeland’s shtick since emerging as a star Liberal candidate in a 2013 byelection in Toronto Centre has been presenting herself as not so different from the Average Middle Class Canuck. Aside, of course, from having degrees from Harvard University and the University of Oxford, being fluent in four languages, conversant in a fifth and owning, as many Torontonians in an inflated real estate market do, a million-dollarplus home. Sure, Freeland, who declined an interview request, is normal. But her normal isn’t the same as you and me.

David MacNaughton, Canada’s ambassador to the U.S., has talked with Freeland almost every day for the past 14 months, and likens her to the “Energizer Bunny,” with an otherworldly capacity to “multitask,” to juggle her job with her private life, and not through half-measures.

The ambassador characterizes the trade negotiations with the U.S. as “tense,” “fractious” and “hanging by a thread.” He describes Freeland as “smart,” “focused” and “determined,” before recalling a conversation he had about her with Canada’s chief NAFTA negotiator, Steve Verheul.

Verheul, a civil servant, and so-called professional negotiator, dealt with the nitty-gritty of the bargaining, and was the point person in a “maple charm offensive,” which saw virtually every member of the federal cabinet make a total of more than 200 visits to the U.S., to plead Canada’s case to members of Congress, state governors and Main Street Americans. But Freeland was different than the rest.

Most ministers want the “two-page” condensed explanation on a complicated file, Verheul told MacNaughton, but she wanted to dive into every fine detail on NAFTA.

“When you talk to her about rules of origin, or the dairy, or intellectual property or whatever — some of these subjects that are extraordinarily complex — she understood them, and could discuss them,” MacNaughton said this week from Washington, D.C. “Typically, politicians don’t — they are interested in the big picture.”

On some level, Freeland is also not afraid of embarrassing herself, despite the big picture. For instance, at the prompting of her children, she was dorky or brave enough — maybe both — to wear a T-shirt with the slogan, “Keep Calm and Negotiate NAFTA,” in public while negotiating said deal.

Nor is she afraid, apparently, of trying to embarrass an American president or disappointing ordinary, hardworking Canadians, as she did in her pre-political life at Thomson Reuters Corp.

Blazing ahead, consequences be damned, can be a handy bit of armour — or an unnerving Achilles heel — for any Canadian politician to possess.

Indeed, Freeland’s jabs at the mercurial Tweeter-in-Chief were many. In mid-June, after being named Diplomat of the Year by Foreign Policy magazine, she gave a speech in Washington. Without naming Trump, she warned of an economic climate where the rich keep getting richer, the middle class feels hollowed out and people become “vulnerable to the demagogue who scapegoats the outsider, the other — whether an immigrant at home or a foreign actor.”

She went on, finger wagging at the Americans — whose soldiers, she lectured, had fought and died alongside our own — for imposing tariffs on Canadian steel and aluminum in the name of national security. A move she described as “absurd” and a “naked example of the United States putting its thumb on the scale in violation of the very rules it helped to write.”

Freeland one-upped herself at the Women in the World Summit in Toronto two months later, appearing on a panel called Taking on the Tyrant. The event featured a video comparing Trump to Russian strongman, Vladimir Putin, and Syria’s murderous Bashar al-Assad.

Critics, on both sides of the border, panned the appearance, questioning how a key member of Team Canada could take the metaphorical equivalent of a bonehead penalty with the game — that is, NAFTA 2.0 — on the line.

If Trump had been simmering inside, he boiled over at the United Nations on Sept. 26, telling reporters: “We are very unhappy with the negotiations and the negotiating style of Canada.” Adding: “We don’t like their representative very much.” According to the Washington Post, Trump said Freeland “hates America” at a dinner for campaign donors the following day.

“I never saw Chrystia react to any of that kind of criticism,” MacNaughton said. “She’s got a pretty thick skin.”

She is also a bulldog. Bill Browder knows Freeland from her days as Moscow bureau chief of the Financial Times. Browder is founder and chief executive of Hermitage Capital Management Ltd., an investment firm that became wildly successful in post-communist Russia, but ran into trouble in 1998 when, as he describes it, “an oligarch started ripping me off.”

Browder, an American, wanted to go public with a story many journalists were afraid to touch. He invited Freeland to dinner at Semiramis, a Mediterranean joint in Moscow. Over hummus and lamb kebabs, he sketched out a tale of financial malfeasance.

“Instead of backing away from the story — because it was such a dangerous story to report on — Chrystia blew it wide open,” Browder said from his London office. “It took a tremendous amount of guts, because gangsters and oligarchs were involved in a lot of murders back then — of journalists and others.

“Chrystia is like raw steel. It is kind of misleading, you know, you see this relatively short woman with a highpitched voice, and you might think you can run roughshod over her. Well, guess what? You will have met your match and 10 times over.”

And yet, even fearless rock-star journalists can present as profoundly tonedeaf and calloused when dealing not in the realm of Russian oligarchs, but of ordinary people.

In 2011, and then based in New York, Freeland became head of Thomson Reuters’s digital news arm, with ambitious plans for launching a new platform, dubbed Reuters Next. The multi-billion dollar information company, majority owned by Canadian billionaire, David Thomson, had opened a digital newsroom in Toronto in 2005.

Freeland embarked on a hiring spree, signing bigname talents for big-dollar contracts, while flitting about the globe — and the American talk show circuit — promoting the Reuters (and her own) brand. Meanwhile, in Toronto, a team of journalists kept waiting to meet their new boss.

“The Toronto staff tried numerous times to engage her as it became more apparent she had no plans to include us,” said one former Toronto editor, who wished to remain anonymous to protect future job prospects in an industry where Freeland remains well-connected. “We were desperate for face time, for some acknowledgment that our jobs mattered and that the hard work we did was appreciated.”

Just a week before Christmas, reportedly at the behest of upper management, Freeland shuttered the Toronto operation, tossing about 25 people out of work and shifting the jobs to Bangalore, India. Freeland’s Canadian employees felt abandoned. But it gets worse: after she leapt into politics in 2013, Thomson Reuters abandoned Reuters Next — without ever launching it — having reportedly spent five million dollars on the failed project. (News accounted for about US$296 million, or three per cent, of the company’s total revenue of US$11.3 billion last year.)

“It was infuriating to see her launch her political bid,” the former Toronto editor says. “Not once did she visit staff at the Toronto office, yet here she was now claiming that this was her home. Her lines on championing the middle class were beyond hypocritical. These were good-paying union jobs that were outsourced.”

Other scars carve deep across Freeland’s personal life. Her Ukrainian-Canadian mother, Halyna (Chomiak) Freeland, was born in a displaced persons camp in Germany in 1946. Halyna grew up to be a lawyer, activist and feminist, and would often bring her infant daughter, Chrystia, with her to class at the University of Alberta law school in the late 1960s.

Halyna and Don Freeland divorced when Chrystia was little. When Chrystia started having children of her own, her mother moved to New York to help. Freeland was running the U.S. arm of the Financial Times when her mother was diagnosed with cancer. But with support, she was able to keep Halyna at home, caring for her at her Manhattan apartment, which is where she passed away on July 6, 2007.

“Halyna was a doer in her life,” said Chrystia Chomiak, Freeland’s aunt in Edmonton. “She did many, many things, and that has had a huge impact on Chrystia.”

Freeland’s family ties remain strong. She phones her father once a week, typically Sunday. Don Freeland said Chrystia is the only one of his four daughters who, as a girl, loved the Peace River farm as much as he does. She used to cut the canola into rows before heading off to school each September. She was never afraid of getting dirty.

On Sunday, Sept. 30, with the fraught trade negotiations at an end, Freeland called her dad. Don griped about the “dairy cartel,” before shifting topics to the grandkids in Toronto. Two summers ago, Chrystia phoned him up, with some specific requests: she needed him to buy some gear at an outfitters and lend her a car, so that she and Bowley could take the family camping in the Rockies.

“Chrystia doesn’t own a car, eh,” Don Freeland said, bemused. “I bought a new one, and told her if one of her aunts wanted to drive my old car to Toronto, that she could have it. But she doesn’t want a car. She rides her bike everywhere.”

And she runs.

IT IS KIND OF MISLEADING, YOU KNOW, YOU SEE THIS RELATIVELY SHORT WOMAN WITH A HIGH-PITCHED VOICE, AND YOU MIGHT THINK YOU CAN RUN ROUGHSHOD OVER HER. WELL, GUESS WHAT? YOU WILL HAVE MET YOUR MATCH AND 10 TIMES OVER. — CEO BILL BROWDER