From the moment Dawn Fitzpatrick stepped onto the American Stock Exchange trading floor as a clerk in 1992, she sensed that the odds were against her. Surrounded by men in jackets barking trade orders, she stood out in her pleated skirt and twin sweater set. Traders around her began wagering over how long Ms. Fitzpatrick, then 22, would last.
"The floor was definitely not a place for people who were cute, prim and proper," Ms. Fitzpatrick said in a recent interview.
Ms. Fitzpatrick began her career at O'Connor & Associates, the Chicago firm that was later acquired by UBS as the Swiss bank's internal hedge fund. She rose to lead the firm and become one of Wall Street's most powerful women. Now, largely unknown outside the industry, Ms. Fitzpatrick faces her biggest and most public challenge yet: working for George Soros, the estimable octogenarian investor and philanthropist.
Last Monday, she started as chief investment officer of Soros Fund Management, which manages around $26 billion of Mr. Soros's personal and family wealth. In taking the job, she follows in the footsteps of finance legends including Keith Anderson, a co-founder of BlackRock, and Stanley Druckenmiller, the billionaire investor. Even Steven Mnuchin, the new Treasury secretary, was once brought in to open a lending business.
Mr. Soros himself is perhaps the finance world's most famous investor. In 1992, he made a $1 billion bet against the British pound. The trade came to be known as one that "broke the Bank of England" when Mr. Soros's heavy selling of the country's currency helped prompt the government to devalue the pound.
But since Mr. Druckenmiller left the firm in 2000, Soros Fund Management has churned through eight chief investment officers. It's a remarkable turnover for the top of any company, even among hedge funds, which are known for a cutthroat culture. It's even less typical in the sleepy world of family offices, where employees manage the assets of a single clan, which is how the Soros funds are now structured after years of accepting outside investor money.
And Soros is not just another family office designed to maximize wealth. There is a direct link between the money that is made at Soros and its founder's philanthropic endeavors. Mr. Soros, now 86, is an outspoken supporter of Democrats including Hillary Clinton, and travels the world seeking to promote democracy. The $1 billion that Mr. Soros made betting against the British pound, for example, helped to support scientists in Russia after the fall of the Soviet Union.
Though Ms. Fitzpatrick is registered as a Republican, she appears unfazed that her investing acumen will in turn support Mr. Soros's activism. "If we do a good job in terms of generating returns, the impact the money created can have is tremendous, and that's really motivating," she said.
Yet Ms. Fitzpatrick, 47, takes over at Soros at a moment of global uncertainty. Impending elections in France and Germany threaten to upset the status quo across Europe. The United States is only beginning to absorb the implications of Donald J. Trump's young presidency. Markets around the world are holding steady but seem liable to drop on any given day.
Ms. Fitzpatrick is bullish. She believes stocks in the United States, having hit record highs, can rise higher still. But she attributes this optimism to what she says are fundamentally healthy companies, not investor giddiness over the Trump presidency. "In reality, if we had Hillary Clinton as our president, I think we'd be here or higher," Ms. Fitzpatrick said.
Buying up the board
At the height of the financial crisis of a decade or so ago, Ms. Fitzpatrick faced the biggest decision of her career. She had risen to become chief investment officer at O'Connor, then a unit of UBS, and now had to steer the firm through a period of market upheavals that would leave some of the biggest names on Wall Street bankrupt.
In the summer of 2008, Ms. Fitzpatrick received a call from Richard S. Fuld, then the chief executive of Lehman Brothers. Mr. Fuld acknowledged that Lehman's stock was tumbling, but he told Ms. Fitzpatrick it would recover and asked her not to pull the billions of dollars that O'Connor had with the bank's prime brokerage, a division that lends stock and cash to hedge-fund clients for trading, in exchange for housing some of the funds' capital.
Ms. Fitzpatrick had a quandary. If she maintained her balance and Lehman managed to survive, she would keep a relationship with a critical Wall Street partner. But if she kept her balance and Lehman went bankrupt, she would lose billions of dollars for UBS O'Connor's clients.
"She did something no one else did," recalled Michael Meyer, a former UBS O'Connor employee who was there at the time. "She quickly assessed the situation with him and said: 'Dick, your stock is trading at $22. If the stock goes to $15, I'm taking half out, and if the stock reaches $10, I'm taking it all out,'" Mr. Meyer recalled.
Ultimately, of course, Lehman failed, triggering some of the worst convulsions of the financial crisis and costing many investors billions. Ms. Fitzpatrick was able to avoid the worst of it, and saved the firm from getting trapped in years of bankruptcy proceedings. Other hedge funds that didn't pull their money were stuck in losing market positions, unable to use their money to make new trades.
Though the episode left her shaken, it was the kind of quick thinking she had prepared for.
Born and raised in Irvington, N.Y., Ms. Fitzpatrick was the middle child among five siblings who grew up in a cul-de-sac on a street bustling with young families. She spent much of her childhood competing with taller, stronger brothers and sisters who excelled at sports like basketball. By her own description, Ms. Fitzpatrick was "short and scrawny." Her father, she said, still jokes that she is the "runt of the litter."
Eventually she found her stride. She turned to running, something she continues to do today, usually at 5 a.m. (She still holds the record for the 3,000 meter run at her high school.)
A neighbor, Marty Atlas, nurtured her early interest in the markets, showing a teenage Ms. Fitzpatrick how stock tables worked. Even as a girl, her investing prowess was evident. "I remember her playing Monopoly with all these other kids, and she ended up with all the hotels," Mr. Atlas said.
Ms. Fitzpatrick quickly zeroed in on her goal for after college: Wall Street. "It was the one place where you could succeed beyond your wildest dreams," she recalled. After graduating from the University of Pennsylvania's Wharton School with a bachelor of science degree in 1992, Ms. Fitzpatrick landed a job with O'Connor & Associates as part of a junior group of American Stock Exchange clerks.
She moved on to trade options for O'Connor at the Chicago Board Options Exchange. There, groups of traders gathered in pits to buy and sell major trading contracts, yelling out their orders while gesticulating madly. Ms. Fitzpatrick, once again an outsider on a testosterone-heavy trading floor, mastered the jargon and the hand signals.
It was in Chicago that Ms. Fitzpatrick learned just how cruel markets could be. In December 1994, an economic crisis was looming in Mexico that resulted in a swift and drastic devaluation of the Mexican peso. Ms. Fitzpatrick was covering a pit where so-called locals — traders who made bets with their own money — were exposed on the wrong side when the American Depository Receipts of Mexican companies moved suddenly. They lost everything.
"Basically overnight, these guys who I would stand next to from 9:30 a.m. to 4 p.m. every day lost their homes, lost their marriages, just everything in a flash," Ms. Fitzpatrick said. "It really left an indelible mark on me."
In the course of her career, Ms. Fitzpatrick has tangled with regulators. While chief investment officer of O'Connor, Ms. Fitzpatrick oversaw the firm's $5.3 million settlement with the Securities and Exchange Commission over charges that from 2009 to 2011 it had bought stocks in companies' public offerings while also taking the opposite position, short-selling those same stocks. The bank denied wrongdoing. More than 23 firms were slapped with similar charges.
"Dawn would see possible risks, multiple layers, beyond anyone else in the room," said Ross Margolies, the founder of Stelliam Investment Management, which Ms. Fitzpatrick and O'Connor seeded in 2007. "It was almost like she was playing a game of three-dimensional chess."
In the world of finance, women can find themselves at a disadvantage, their careers stymied by overt sexism and implicit bias alike. The paucity of senior positions held by women in banks and other financial firms, which a recent Financial Times survey put at less than 26 percent, would seem to underscore that belief.
As the first female chief investment officer at Soros, Ms. Fitzpatrick becomes a woman with few peers; most everyone managing such a large pot of money on Wall Street is a man.
Ms. Fitzpatrick said that, on the whole, she has not felt discriminated against because of her gender in the workplace. At UBS, Ms. Fitzpatrick kept a pair of Christian Louboutin shoes under her desk but often walked around the office barefoot, a display of her confidence.
"Clearly, there are single moments in time when I would have rather been a 6-foot-3 blond-haired ex-football-playing guy," she said. "But those tended to be offset by the times when I thought it was an advantage to be a woman."
Ms. Fitzpatrick says women have innately useful qualities when it comes to money management. "One of the things I believe women have more of is humility in their investments," she said. "We'll cut losers quicker, in a more effective way, than generally men will." Indeed, some studies suggest that women are more successful risk managers than men.
Yet Ms. Fitzpatrick has also caught herself masking her femininity to keep up with her male colleagues. Days after giving birth to her second child, she was on a flight to London for a meeting wearing several layers of Spanx, the tightfitting undergarments meant to conceal extra pounds.
"From my perspective, perceptions matter, and it was important for me that I was there," she said. "I didn't want them to think I was anything but focused."
Such hard-driving ambition can be a distraction, too. A few years later, in the summer of 2008, Ms. Fitzpatrick was so consumed by her work that she didn't realize she was pregnant for several months. The financial crisis was beginning to unfold, and the markets were swinging violently. She was often sick to her stomach, and was also getting heavier, but she figured her discomfort was a result of her stress. Plenty of her peers were having visceral reactions to the crisis.
"The fall comes, and I'm nauseous, and I'm gaining weight, and it doesn't even cross my mind that I could be pregnant," Ms. Fitzpatrick said.
Today, Ms. Fitzpatrick maintains the long hours and relentless travel schedule common among financial executives. It keeps her away from her three children and her husband more than she would like.
But she lives in Irvington, the town where she grew up, and her two sisters and her parents still live nearby. They help with the children. She admits, however, that her relentless drive is "not necessarily a virtue for everyone."
Keeping up with Soros
In her new role, Ms. Fitzpatrick oversees assets that Soros Fund Management invests directly, as well as more than a handful of outside hedge fund managers and private equity firms. It is similar to the role Ms. Fitzpatrick played at UBS O'Connor several years ago. And during her last year at the Swiss bank, she held a more strategic role, managing teams across all of UBS's asset management unit, and overseeing more than half a trillion dollars.
It was a prestigious job, but one that removed her from the day-to-day trading and market strategizing that associates say she loves most.
Now, "she will basically be able to sit down with those managers whom they've allocated money to, and really be able to speak the language," said Rich Cunningham, a managing director at Barclays Investment Bank.
Among the new challenges she will face is all that turnover at Soros.
Ted Burdick, the previous chief investment officer there, stepped down after just eight months on the job, though he remains with the firm. Others who have held Ms. Fitzpatrick's role have been caught up in the internal politics of the firm, and at times clashed with Mr. Soros himself.
Ms. Fitzpatrick may be at less risk because, unlike some previous chief investment officers, she will be reporting to the family office's board of directors, rather than just Mr. Soros, who is the chairman of the board.
And yet Mr. Soros, one of history's best traders, still can't help but sometimes want to manage his own money.
Last year, as Britain prepared to vote on whether to exit the European Union, Mr. Soros stepped back into his day-to-day engagement, placing wagers that would be affected by the June referendum. The "Brexit" outcome, a surprise to many, triggered significant market swings, and Mr. Soros benefited from a position that predicted shares of Deutsche Bank would fall, among other trades.
Later in the year, however, Mr. Soros lost around $1 billion wagering that Mr. Trump would lose the presidential election.
Beyond his occasional trading, there could be a disconnect between Mr. Soros and his new chief investment officer. Speaking at the World Economic Forum in Davos, Switzerland, in January, Mr. Soros mixed his views on politics and finance to deliver a bleak economic prognosis.
Yes, investors were bullish, thanks to the belief that Mr. Trump would dismantle regulations and reduce taxes. But, he said, Mr. Trump would fail to achieve those policy goals. "I don't think the markets are going to do very well," Mr. Soros said.
Ms. Fitzpatrick, however, says that although she is more bullish on the stock market than her boss, they are not out of sync on the big picture. "As an investor," she said, "you have to continuously evolve and learn."