Annie Duke Will Beat You at Your Own Game

I wrote to the retired professional poker player about the possibility of profiling her. We spent the next few weeks engaged in a polite game of psychological warfare.
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At high-profile tournaments, Duke was usually the only woman at the table.Photograph by Charly Kurz / Laif / Redux

Late last year, I wrote to Annie Duke, a former professional poker player, about the possibility of profiling her. Duke, who for years was the leading female money winner in the World Series of Poker, retired from the game six years ago and has since refashioned herself as a corporate speaker and strategic consultant. She struck me as someone with a potentially unique and strange set of perspectives on gender, celebrity, and money. We spent the next few weeks engaged in a polite game of psychological warfare. I became attuned, moment by moment, to infinitesimal shifts in power and grew obsessed with the notion that she might be playing our negotiations like a card game. I’m still not sure how much of it was in my head.

At first, Duke enthusiastically agreed to be profiled, and often responded to my e-mails with smiley faces and exclamation points. She invited me to accompany her to a charity event and suggested that I come along to her brother-in-law’s birthday party. When I asked her to recommend friends and colleagues who might have insight into her career, she responded eighteen minutes later with an annotated list of twenty-seven names. It included all living members of her immediate family, her ex-husband, various professional poker players, and celebrities she has taught to play the game. Duke seemed to understand instinctively that affording a journalist access can actually be a form of self-protection: her avid participation would decrease my need to ferret out potentially unflattering material elsewhere.

Since retiring, Duke, who has four children and lives near Philadelphia, has travelled across the country delivering keynote speeches to conferences held by the likes of Citibank, Pandora, and Marriott. She has co-authored multiple gaming guides, and her first general-interest book, “Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts,” came out in February. The book’s premise is that poker players live in a world in which “risk is made explicit” and are therefore trained to assess incoming information logically and judiciously in a way that other people are not. “A hand of poker takes about two minutes,” she writes. “Over the course of that hand, I could be involved in up to twenty decisions. And each hand ends with a concrete result: I win money or I lose money. The result of each hand provides immediate feedback on how your decisions are faring.”

Duke argues that we bet all the time: on parenting, home buying, restaurant orders. Betting is merely “a decision about an uncertain future,” and our opponents are not other people but, rather, hypothetical versions of ourselves who have chosen differently than we have. Her most urgent message is that we should all be more comfortable living with self-doubt—not for ethical reasons but for intellectual ones. Embracing uncertainty, she argues, makes you a better thinker. “Real life consists of bluffing, of little tactics of deception, of asking yourself what is the other man going to think I mean to do,” she writes, quoting John von Neumann, the father of game theory.

Coming from someone younger or dumber, Duke’s eagerness in her interactions with me would have seemed naïve or even reckless, but Duke is fifty-two, media-savvy, and known for a career defined by analytical thinking. It was safe to assume that her openness was not just intentional but strategic. Duke has two decades of experience exploiting information asymmetry, and a professional obligation to trick people into acting against their own best interests. I worried that, no matter how wary I remained of Duke, she would, in the end, beat me at my own game.

I met Duke for the first time on the afternoon of December 11th in the marble lobby of the Franklin Institute, a science museum in downtown Philadelphia. Duke is a trustee, and she invited me to join her at what she warned might be a dull board meeting, followed by a holiday party also at the museum. Duke shook my hand warmly and asked whether I would mind venturing outside for a quick bite to eat. I wondered how we would possibly make it back in time for the board meeting, which at this point was scheduled to begin in five minutes. “I’d like to just have a regular conversation,” she told me. “There are a few sensitivities I’d like to discuss, since we’ve never even spoken in person.”

This seemed reasonable, even admirably prudent, if a bit oddly timed. And, anyway, arguing with her about it would be an unwise first play. I agreed.

“I’m vegan, so this can be tricky,” Duke said as we exited the museum. We passed a couple of coffee shops, but it seemed unlikely that they would offer anything she could eat, and we finally found an Indian restaurant a few blocks away. She ordered a curry, made without meat or ghee, and seemed unconcerned about missing the meeting.

Duke has red hair and an unnerving gaze. In her 2003 memoir, “Poker Face,” Duke’s younger sister, the poet Katy Lederer, describes Duke’s way of talking as “just this side of taunting, a clipped, carousing voice that would carry through a room.” Lederer depicted their childhood—spent on the campus of a tony Episcopal boarding school in New Hampshire—as marked by constant class consciousness and pained proximity to erudition. Their father, a self-styled eccentric and the son of Jewish immigrants, was a linguist and English teacher; their mother was an alcoholic homemaker with thespian aspirations. The two argued ferociously. From the constant domestic combat, the siblings—Annie, Katy, and their older brother, the professional poker player Howard Lederer—learned the importance of rhetoric, and of winning.

Duke moved to New York City after high school and attended college at Columbia. Near what should have been the end of graduate school, at Penn, she developed a stomach illness and dropped out. She and her husband at the time moved to rural Montana, where he was from. There, in the basements of dusty saloons, she learned to play poker, competing against ranchers and retirees. Soon after, the couple moved to Las Vegas, and over the next twenty years Duke’s life took on the outlandish rhythms of a Steven Soderbergh movie. She became the first woman to win two major tournaments in a single year; she played in the World Series of Poker while nine months pregnant; she testified in Congress (twice) to support the legality of online betting.

Duke’s career coincided with a renaissance of the game. Poker, which for decades had been seen as a habit of mobsters and gambling addicts, was, by the early nineties, a part of mainstream culture. At high-profile tournaments, Duke was usually the only woman at the table. She appeared on “Good Morning America” and “Late Show with David Letterman”; she was written about in People magazine and in national newspapers. She became an object of fascination and, inevitably, misogynist scorn. Duke gave an interview to NPR in 2015 in which she elegantly explained three types of men she often encountered at card tables: disrespectful chauvinists (men who patronized women), flirting chauvinists (men who sexualized women), and angry chauvinists (men who hated women). She had strategies for beating all three.

In 2009, Duke appeared on “The Celebrity Apprentice,” alongside Joan Rivers, Dennis Rodman, and Khloé Kardashian. In one episode, a long-simmering feud between the two eventual finalists, Rivers and Duke, bubbled over. “She seems nice to me,” Donald Trump said of Duke. “She does seem nice,” Joan Rivers responded. “So was Hitler at Buchenwald.” Though Rivers ultimately won the season, Duke clearly drove her mad in the process. “Annie is a very good poker player, obviously, but plays people like she plays poker,” Rivers later said.

In 2011, her brother’s online betting company was investigated by the Justice Department on suspicion of money laundering and gambling violations. He settled personally, for two and a half million dollars, in 2012, without admitting wrongdoing. The same year, the parent company of the Epic Poker League, of which Duke was the commissioner, filed for bankruptcy. In 2013, a series of leaked audiotapes seemed to suggest that five years earlier, despite protestations, Duke might have been aware of fraudulent play and the use of unauthorized software codes on ultimatebet.com, an online poker company that she endorsed and played for. Duke vehemently denied cheating.

Despite her tenacious self-presentation, I liked Duke a lot. Between bites of curry, she expressed real vulnerability and said smart, interesting things, many of which I wish I could quote. But she didn’t want me to turn on my recorder, and, from the moment we sat down, she expressed hesitation about doing the Profile at all. This was surprising. Hours earlier, Duke had been all in. She was concerned, in part, that in writing about her I would have to write about her friends and family. For the moment, at least, she talked about them only off the record. We stayed at the restaurant for two hours, and by the time we left it was dark.

As we walked back to the museum, where she had parked her car, Duke shivered. “I had it all gamed out. I wore this cute jacket because I thought I’d be going from the underground parking garage straight inside, but here we are,” she said, laughing. It was thirty-seven degrees out. “How’s that for rational decision-making?” Duke made no mention of the board meeting or the party, both of which she had missed, and I wondered when she had decided that we would skip them. The state of play at this point was ambiguous. Was she trying to get out of doing the Profile, or was she merely pretending to hesitate?

I spent the train ride back to New York not knowing what to feel. I remembered that the first thing Duke ever asked me was for constructive criticism of her book. “Thinking in Bets” would be out in two months, and nothing I told her would have been actionable so late in the process, a fact she must have known. But it was a clever thing to say: it exposed her, and flattered me. Or, maybe, as someone who earns a living through speaking fees, she really did want my opinion? I felt like I was going crazy.

For the next few days, Duke and I remained in touch. She said she still wasn’t sure if a Profile was a good idea, but that she was thinking seriously about it and would let me know soon.

Her brother-in-law’s birthday came and went. I reread parts of her book but refrained from calling any of the twenty-seven people she had recommended. Finally, she e-mailed me—subject line: “Decision”—to let me know, in kind and complimentary terms, that she had decided, for the sake of her family’s privacy, not to participate in a Profile. In her book, Duke praises the benefits of “recruiting people” into one’s decision-making, and I suspected she had likely done just that, though whom she would have recruited I wasn’t sure. A few days later, I told her that I’d still like to write something about her—“a critically-oriented essay about ‘Thinking in Bets’ and your career” is how I phrased it. Duke agreed that we could speak again, but she didn’t, as I was hoping, relent on the matter of the Profile. She wasn’t bluffing.

Weeks later, I called Duke to ask what, exactly, had happened. She told me that at first she was genuinely pleased by the attention, which was why she so readily began calling and e-mailing and making generous suggestions. “But then it was, like, ‘Hold on a second!’ ” she said. “I had to very consciously remove myself from that excited state.” Duke was, to use a term from her book, fighting against temporal discounting, which she describes as “the tendency we all have to favor our present-self at the expense of our future-self.”

She went on, “So we had our long talk and I found you delightful, but whether I liked you or not I knew that wasn’t the right question. I had to remind myself to think about how I’d feel if the final product were really great, you know, according to me. And, if I’m honest, I know that even in a very generous Profile of me I wouldn’t like twenty per cent of it. That’s probably the best I could hope for, realistically. But not liking it wasn’t the problem. I want people to engage with the ideas in the book, not with me.” I told her that they seemed to be one and the same. “It’s true,” she conceded. “I guess I really do live this book.”

The next day, Duke put me in touch with Michael Naidus, a television producer and one of her best friends. They met fifteen years ago, when Naidus booked Duke as a guest on “The Late Late Show.” “He knows me in all my incarnations,” she said. When I called Naidus, he was driving around Los Angeles. “Of course, Annie, like everyone else, operates with some artifice,” he said. “But the thing is, this stuff works. It’s not like a backhand in tennis, which would never help you off the court. Knowing how to read people with whom you have an uncertain relationship, people who may or may not be telling the full truth, is an undeniably useful thing.” I asked if Duke had told him anything about our conversations. “Oh, I know all about everything,” he said. “For what it’s worth—and why should you believe me?—but I really do think she was being completely genuine with you. That said, you were clearly victimized by the very thing she writes about!”

Had there ever even been a board meeting? In early January, I called the museum. A woman in the development office picked up and confirmed that there had been one at four-thirty on the afternoon of December 11th. I felt like a self-tormenting teen-ager, overanalyzing her crush’s silence only to find out, hours later, that his phone had run out of battery. Then, she said, “Are you calling because of Annie Duke?” I told her I was and asked how she knew. She just laughed.