She is many things that would seem to irritate President Donald Trump: a liberal Canadian former journalist.
That makes Foreign Minister Chrystia Freeland an unusual choice to lead Canada's negotiations over a new free trade deal with a surprisingly hostile U.S. administration.
Recruited into politics by Prime Minister Justin Trudeau, Freeland has already clashed with Russia and Saudi Arabia. Those who know her say she's unlikely to back down in a confrontation with Trump.
"She is everything the Trump administration loathes," said Sarah Goldfeder, a former official with the U.S. Embassy in Canada.
Freeland, a globalist negotiating with a U.S. administration that believes in economic nationalism and populism, hopes to salvage a free trade deal with Canada's largest trading partner as talks resumed Wednesday in Washington. The 50-year-old Harvard graduate and Rhodes scholar speaks five languages and has influential friends around the world.
"I have enormous sympathy for her because she is negotiating with an unpredictable, irrational partner," said CNN host Fareed Zakaria, a friend of Freeland's for 25 years.
Freeland cut short a trip to Europe last week after Trump reached a deal with Mexico that excluded Canada. Talks with Canada resumed but Trump said he wasn't willing to make any concessions.
The Trump administration left Canada out of the talks for five weeks not long after the president vowed to make Canada pay after Trudeau said at the G-7 in Quebec he wouldn't let Canada get pushed around in trade talks. Freeland then poked the U.S. when she received Foreign Policy magazine's diplomat of the year award in Washington.
"You may feel today that your size allows you to go mano-a-mano with your traditional adversaries and be guaranteed to win," Freeland said in the June speech. "But if history tells us one thing, it is that no one nation's pre-eminence is eternal."
Despite being the chief negotiator with the Trump administration, Freeland has criticized it when few other leaders of Western democracies have.
"She's an extremely strong-willed and capable young woman, and I think Trump generally has a problem with that," said Ian Bremmer, a longtime friend and foreign affairs columnist and president of the Eurasia Group. "She's not going to bat her eyelashes at Trump to get something done. That's not Chrystia. She doesn't play games."
After Freeland and her department tweeted criticism of Saudi Arabia last month for the arrest of social activists in the kingdom, Canada suffered consequences. The Saudis suspended diplomatic relations and canceled new trade with Canada and sold off Canadian assets.
Peter MacKay, a former Canadian foreign minister, said public shaming like that doesn't work and said some Americans viewed her June speech in Washington as something less than diplomatic.
"It was around that time, within days, that the U.S. threw Canada out of the room," MacKay said. "There is sometimes concern that she is taking the lead from her prime minister by playing a little bit to a domestic audience."
Trudeau personally recruited Freeland to join his Liberal Party while it was the third party in Parliament in 2013. Freeland had a senior position at the Reuters news agency but was ready to move on after setbacks in her journalism career, said Martin Wolf, an influential Financial Times columnist and longtime friend.
Freeland previously had risen rapidly at the Financial Times where she became Moscow bureau chief in her mid-20s during the collapse of the Soviet Union.
Freeland also served as deputy editor of the Globe and Mail in Toronto and the Financial Times. She had designs on becoming editor of the Financial Times but left after a clash with the top editor. She was familiar to many TV viewers in the U.S. because of her regular appearances on talk shows like Zakaria's.
"She was a godsend for us, frankly, because she is so bright and so talented and articulate," Zakaria said. "She is as about as impressive a person as I have met."
Freeland, who is of Ukrainian heritage, also wrote a well-received book on Russia and left journalism for politics in 2013 when she won a district in Toronto. She has been a frequent critic of Russian President Vladimir Putin, who banned her from traveling to the country in 2014 in retaliation for Western sanctions against Moscow.
She remains chummy with journalists, even bringing them frozen treats in 90-degree heat last week while they waited outside the U.S. Trade Representative office in Washington.
Bremmer, who met Freeland in Kiev in 1992, good-naturedly chided her for a strange foible: a habit of writing notes on her hands even when she has notepads.
"I have seen in her environments with foreign ministers and heads of state with stuff on her hands," he said with a laugh.
Throughout her career, Freeland has cultivated an impressive group of friends. Mark Carney, the Bank of England governor, is a godfather to one of her three children. Friends include Larry Summers, the former U.S. treasury secretary, and billionaires George Soros and Stephen Schwarzman, the Blackstone Group chief executive who once led one of Trump's disbanded business councils.
"I always found her to be extremely smart and easy to talk with," Schwarzman said. "She accessible and direct and quick. You don't get to be a Rhodes scholar by accident."
Summers is a mentor from Harvard.
"Her clarity of thought, straightforwardness and deep sense of principle make her an ideal leader of the international community as it responds to highly problematic American policy," Summers said in an email.
Bremmer said Freeland has serious globalist credentials, "but right now, momentum is not with that group globally."
When Trudeau became prime minister in 2015, he named Freeland to his Cabinet. She served as international trade minister and worked on ensuring that a free trade deal with the European Union didn't unravel. At one point, she left stalled talks near tears after saying it had been impossible to overcome differences. An agreement was reached not long after that, and Freeland received credit.
Now she's facing her toughest challenge with the North American Free Trade Agreement, since the U.S. represents 75 percent of Canada's exports.
"Canada is stuck with the United States. That's Canada's trade," Bremmer said. "Canadians are going to have to swallow a fair amount of pride. They are going have to pretend they like this guy a lot more than they obviously do or they risk getting much more economically punished. That's just the reality."