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Magic Man

With a deck of cards and tricks up his sleeves Ryan Oakes is well suited to the world of illusion

Waco, Texas. It is a location known, rather infamously, for being the onetime residence of the Branch Davidians, a religious cult whose compound went up in flames during a 1993 siege with federal agents. It’s also the improbable place that Leah, a doe-eyed twenty-something who works with a group of Manhattan financial consultants, is using to try to stump the amazing Ryan Oakes at a SoHo hotel party.

So far, Leah’s lost a cigarette to Ryan—he made it disappear—and she’s watched him deftly convert a dollar bill to a crisp $100 with his rapid-fire sleight-of-hand. But now Leah is convinced she’s got him. At Ryan’s behest to “think of a place,” she’s discreetly written “Waco” on a piece of paper and slipped it into an envelope, while warily eyeing him to see if he’s got something up his pin-striped suit sleeves. Ryan reads her mind, sort of. “You think there’s magic ink in there that only I can see,” he says to her, laughing as he recognizes her skepticism He’s used to it. “Every audience has at least one [skeptic].”

Ryan picks up an artist’s sketchpad, scratches his chin and quizzes Leah about what’s secreted in her envelope. “Is it a place where you would go to have fun?” he asks. “Most people wouldn’t, but I did,” she teases. Ryan nods, and looking reasonably satisfied, writes on his pad and turns it to the gathering crowd. On it read, “Waco, Texas.”

Leah drops an expletive along with her jaw. “How did you do that?” she screams, and shakes her hands at Ryan as if to ward off an encroaching spirit. And just like that, the amazing Ryan Oakes has done it again.

How Does He Do It?

The intimate group of revelers who have invited Ryan to regale them over cocktails at the exclusive bar of the swanky James Hotel erupts in cheers. Normally brash financiers, whose workaday dealings are so discreet they’ve asked to remain anonymous here, are reduced to awestruck wonder. They circle Ryan with their beers and martinis, coyly peering up his sleeves, studying his every move in a desperate attempt to answer the how-did-you-do-that question his always rapt audiences often ask. It’s a curious reaction that never really gets old for Ryan, the thirty-four-year-old conjuror extraordinaire who’s been called one of the “hottest magicians working today.”

“People always ask how, always try to take it down to ‘What’s the secret?’ But for me it’s not about how I do it,” Ryan says. “I love when I alter the way people see the world around them and change their perception of things. For me it’s about the wonder.”

For Ryan that wonder was born in Stamford at the Palace Theatre, where at the impressionable age of eight, this native son experienced the same magical awe he now evokes in appreciative audiences near and far. As Ryan tells the story, his father, Max, took him to the landmark theater to see a performance by master illusionist David Copperfield. “David ended up in the audience right behind me sitting on someone’s shoulders,” Ryan reminisces, still enchanted by the memory of Copperfield’s seemingly mystical ability to float around a theater.

“It was big,” Max recalls of his son’s reaction. “I think that’s the day he really got bit.”

At the age of eleven, wearing a red satin-lined cape hand-made by his grandmother, Ryan performed his first paid gig at Stamford’s St. Mark’s Episcopal Church. “I think I got twenty bucks, but I loved the idea of getting paid for doing what I loved to do,” he says. Soon his mom, Patricia, was driving him to $75 performances at local birthday parties.

Now a sought-after fixture on the corporate and charity party circuit in Fairfield County, Manhattan, the Hamptons and beyond, Ryan has managed to pull an intriguing career out of the hat of his childhood obsession. These days he brings his thoroughly modern magic tour to rarified events with guest lists that include celebrities, titans of business, royal scions and his personal favorite, American military troops. The short list of people he’s dazzled includes Tommy Hilfiger, Mary J. Blige, actors Laura Linney and Sarah Jessica Parker, rapper LL Cool J, Tom Colicchio of Top Chef, Henry Kissinger, New York City Mayor Michael Bloomberg, and more. He’s entertained in the Clinton White House and on private yachts, opened for burlesque queen Dita Von Teese and delighted soldiers stationed at Guantanamo Bay.

What Ryan won’t do is headline a traditional nightclub act. He deliberately eschews these in favor of more exclusive, intimate performances. Calling himself “an entrepreneur at heart,” Ryan is devoted to creating unique experiences at events that range from million-dollar weddings to corporate shindigs for elite executives. “I don’t cut ladies in two,” he says. “I don’t wear a cape or a top hat anymore. I don’t have—or really want—my own Vegas act.” He’s happiest stepping directly into a well-heeled crowd with a crisp deck of cards in his pocket and putting a charismatic new spin on some classic tricks. “When I realized I could have a career like this, where I could engage with people in a more personal way, well I did everything I could to make that happen.”

Now He Sees It

Magicians tend to be nerds, Ryan says over a recent lunch in New Canaan. It’s a comment that is quickly challenged once uttered since nothing about Ryan skews nerd. With his natty blazer, gleaming blue eyes and shock of dark brown hair, Ryan looks more like a crush-worthy Brooklyn hipster than a suburban geek. “Well, I played sports and everything,” he says of his Stamford childhood. “But there’s something about magicians. We’re obsessive in a way that makes us kind of geeky.”

After attending New Canaan Country School, where his mom still works, Ryan was a class officer at Westhill High as well as an editor of the Westword, the school’s award-winning newspaper. “I would say he was the all-around good kid, popular and smart,” says his dad. “He could do anything he put his mind to, especially if he had the passion for it.” After graduating from the University of Pennsylvania, Ryan expected to parlay his psychology degree and insatiable curiosity about people and technology into an advertising career. With impressive internships already on his resumé, he was poised for his Madison Avenue career to take off when the economic downturn after the 9/11 terrorist attacks evaporated his prospects. “All my contacts were suddenly unemployed too,” he says.

Encouraged by his parents, he took a year to concentrate on magic, the one constant in his life. “Some kids grow out of it, but I never did,” Ryan explains. “But as much as I wanted it to be a career, I think I had a bit of that practical mindset that it couldn’t really be a career without an office and a desk.”

Now, his father observes, “it seems like he’s going from one billionaire’s party to the next.”

Ryan credits his rise not only to his entrepreneurial instincts, but to the training he received from a masterful mentor, the late Bill Andrews, a longtime Stamford resident and former president of the Society of American Magicians (SAM).

Ryan met Andrews, who passed away in 2011 at ninety-two, when the veteran magician was performing at a benefit at King Low Heywood Thomas school. “In Ryan, Bill recognized the spark of a good magician right away,” says Andrews’s widow, Helen. “Even as a little boy, Ryan was so elegant and charming and eager to learn. We had two boys of our own who weren’t all that interested in Bill’s magic, but Ryan would come over and spend hours learning tricks in our basement. Bill had many kids he mentored, but I think I can say that Ryan was a favorite because he was so innovative and charismatic. Even then he liked to put his own spin on things.”

Andrews demonstrated his belief in his protégé, by offering Ryan an early entrée into the close-knit world of magicians. “We may seem like a secret society, but we’re actually very clannish and open with each other,” explains Ryan, who now counts Copperfield, the sensational David Blaine and Vegas icons Penn & Teller—for whom he once interned—among his collegial acquaintances.

Andrews also inducted Ryan as an inaugural member of SAM’s youth division, and one year invited his disciple to perform at a junior competition the society was conveniently hosting at the Stamford Hilton. On contest day, the already nervous Ryan learned there was a hiccup: “Not enough kids signed up and they were canceling the youth event, so I had to compete against the grownup magicians.” Eleven-year-old Ryan took on the big capes and won. “I think if I had to pinpoint a moment when I believed it was possible to be a real magician, that was it,” Ryan says.

Playing His Cards Right

“Is it corny to say he’s magical?” asks Brian Lessard, group vice president of global operations for Stamford-based Affinion Group who, on a tip from a friend, hired Ryan for a memorable company holiday party several years ago and is now a repeat customer. “The really cool thing about Ryan is the way he kind of inserts himself in a crowd and surprises everyone. He just shows up like he’s Joe from accounting. Then he takes over the conversation and starts doing tricks.”

During Ryan’s first booking, adds Lessard, “I found myself following him around the room just to see if I could figure it all out. What was amazing were people’s responses to him. It was total bewilderment, then total wonder. First it’s ‘Who is this guy?’ And then it’s ‘How does he do it?’”

Lessard was so impressed he recommended Ryan to headline a private event that included the CEOs of some Fortune 500 companies. More work came from that gig, often the way it is with Ryan, who says word-of-mouth is his biggest form of self-promotion.

What is fun for Ryan is the effect he has on a crowd. Once a gathering has witnessed him make a deck of cards move on the floor levitation-style, they’ll circle, prod and offer guesses on how he pulled off the trick.

Ryan is particularly adept at taking these hyper-curious sorts (“often they are engineers and scientists”) and working them to his advantage in much the same way a comedian can make a heckler part of the act. “I tend to deal with a highly sophisticated crowd of people who really aren’t used to not being in control. What I create for them is a fleeting experience that tends to evoke a kind of childlike wonder. It’s something most of us don’t really experience in our daily lives anymore.”

It’s why, back at the James Hotel, Leah became Ryan’s de facto muse. Her insistence that she could “get” Ryan made it even more spectacular when Waco, a place she later said she had visited on a college road trip, appeared out of mental thin air.

Maybe it’s his psychology background, but Ryan admits to an uncanny ability to read people and their subtlest cues. It can be nuanced things—the blink of an eye, the tiniest twitch—that can hint at deception or belie an answer. Maybe that works when you’re guessing someone just pulled the ace of clubs from a deck of cards. But Waco? Really? How did he do that?

“Ah, you really don’t want to know,” he finally says. “It would ruin the magic.”  

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