Jesse, a 27-year-old former New York City investment banker, moved to Buenos Aires 11 months ago. In the last few months, he says the trickle has turned into a full spray: On average he meets two new arrivals a week. “There is a huge global migration of newly unemployed bankers to Buenos Aires,” he said. “The funny thing is that most of them claim that they left voluntarily, but none of them can say that while they look you in the eye.” Talk naturally turns toward the Wall Street crash. “There is an instant sense of community,” said Jesse. “If you think about it, losing a high-paying job that you worked your entire life to acquire is a very traumatic experience. I can’t tell you how many emotional conversations I have had discussing how it happened, how you feel about it, what your plans are. Most have decided the industry is over and have no idea what they want to do going forward.”
On a sunny Sunday afternoon in January, he saw David Webb. “He was aimlessly walking down the street by himself with a look of satisfaction and curiosity. I immediately recognized him; after all, he is a very handsome Canadian with a chiseled jaw line.”
FOR THE LAST four years, up until a week ago, David Webb worked at Goldman Sachs. In January he spent two weeks hanging loose in Buenos Aires. He was also there checking out real estate investment opportunities. A friend of Mr. Webb’s had told him to come down and have a look. Within a day of arriving, he found himself dealing with more New York bankers than he does in New York.
“You’d start the day at a park and then run into five former bankers, and then you’d wind up at a bar and all of a sudden there would be 15 of them,” Mr. Webb said. “Ex-bankers, ex-traders, Lehman guys, Bear guys, everyone. Guys that got screwed by their job and came to a place where everything was cheap. It’s fuckin’ beautiful and the sun was going down at 9:30.”
He said that some of these young bucks, most of whom hail from New York and London, have embraced their new lives. But for most, with a few drinks comes a fountain of griping and grumbling, bonuses, bonuses, bonuses. Mr. Webb fled to Uruguay for a few days.
“It did kind of crystallize things,” said Mr. Webb, 26. “I came home to New York and everyone was just fucking depressed. I tried not to get infected as I reintegrated myself into the working world.”
Last Thursday was his last day at Goldman. “Laid off” is a vague term, and Mr. Webb is not permitted, under the terms of his employment, to be specific.
Not one to be left out of pocket or out of a lark, a few weeks before packing up his desk at Goldman he’d pushed his way into an interview at Wilhelmina Models. He recounted his side of the initial phone conversation, which had started off with him making the mistake of telling a woman at Wilhelmina he was 6-foot-4—he’s actually 6-foot-3 and a half—thinking such impressive altitude would work in his favor, when actually the industry likes male models to top out at 6-foot-2.
“Dana, Dana, Dana, Dana, Dana, Dana, listen, Dana, I’m not six-four,” said Mr. Webb, trying to recover. “Dana, I’m not six-four, I’m six-two. I have a long neck. Dana, Dana, let me just come in, let me in.”
It worked. On Feb. 3, having taken the afternoon off work—which friends say was not an uncommon practice in recent months—he poured himself a Scotch, neat, and set off on foot from his one-bedroom apartment in Soho to the Wilhemina offices on Park Avenue South.
“Dana was a treat, I rapped out with her,” he told me on a recent afternoon over a couple pints of beer at a pub on East Ninth Street. “Dana was like, ‘You got no experience.’ She’s like, ‘I don’t know if you can make money as a male model.’ She’s like, ‘I don’t know if you can make $12,000 as a male model, I don’t know if you can make 12 grand.’ And I’m just like, ‘What the fuck is this 12 grand number?’ I was like, ‘I guess I gotta just make 12 grand.’ So I’ve been keeping a tally; I’ve made $200 so far. I’ve been trying to make 12 grand before I go back to her. And I’m going to go back to her and be like, ‘I made 12 grand.’”
He got the two crisp ones for a day spent walking around Helen Yarmak’s fashion week showroom, wearing fur coats. Ms. Yarmak freaked out about his hair, which is curly and does its own thing. The stylist struggled to give it a part and kept telling him to keep his chin up. His instinct was to gaze off, serious-like, at some imaginary point in the distance. He now knows he needs to work on being more animated.
“Someone says ‘O.K., go,’ and they all start doing stuff,” he said. “I don’t know what to do. So I need to learn some new moves. It’s like, ‘Look angry. Look angry. David, thrust your neck out.’ And then it’s like, ‘Look sexy!’” He pursed his lips. “It’s just like the same look! ‘Look confused!’”
“I was struck by how comfortable David was in front of the camera,” said photographer Steven Benisty. “In the last few months, I’ve done three people who have been laid off from their jobs in finance and are trying to make the transition to modeling, and they are usually very awkward in front of the camera.”
Mr. Webb is Canadian. He said his pursuit of modeling has more to do with getting his Visa renewed than with fulfilling a dream, which of course is what he’s telling agents.
“If you’re not willing to call people over and over and send them follow-up emails—then it just doesn’t happen,” said Mr. Webb. “I’m very good at doing—now I am, it took four years—but I’m very good at doing tasks where it’s just spending a certain amount of time and just doing them.” He said he’s got enough money to live comfortably in New York for two years.
“It sounds silly,” he said, “but the idea is to take this time to start training my body and mind again. Gotta set it in motion again. I burned it all up. All my former athleticism and studying is burned up, and I’m left with an injured mind and a dead body. I need to remedy that.”
He was born in Toronto. His father, Ian, is a lawyer with a venture capital business. His grandfather was a loyal employee of Merrill Lynch Canada. His older sisters both played competitive tennis, one went pro. Spider Webb—as the kids called him—followed. Every day after school, his dad would drive him to the National Tennis Centre an hour outside the city. Tennis, he said, “is a quirky game that you find yourself thinking about all the time, which is kind of nice. It’s a year-round sport that you have to play constantly. If you take a week off, you can’t win points.”
He went to an all-boys private school; he lost his virginity his last year there. “It took a long time to get that monkey off my back; eventually a very patient girl held my hand through it,” he said.
He was still dating that patient young lady when he arrived at Dartmouth for preseason. By junior year, he was playing No. 1 singles on the tennis team. He battled the great Johnny Chu of Harvard for the title senior year. Indoors and everyone was there. He said he played “lights-out” (a tennis expression for playing your best game). He lost, and decided his tennis career had run its course.
“Dartmouth turned out to be a pretty conservative school,” he said. Each year, the recruiters would show up. “Lot of pressure when the banks come into town,” said Mr. Webb. “The people that came to campus were the consulting companies and investment banks. So you’re doing Bain, McKinsey, Parthenon and whatever—all the Boston places—and, you know, Goldman, Lehman and all those guys. So all of a sudden everyone’s walking around in suits with these leather Dartmouth folders with résumés in them. There was a feeling that everyone was kind of interviewing. Also because you just make such a fort …” he paused. “It was good money for a young guy, and if you didn’t know what you were gonna do, it was intense, it was competitive and it was somewhere that you could actually be challenged. It’s like you pick a direction and start sprinting, you know, which is the idea.”
The summer of ’05, he moved to New York to begin work for Goldman Sachs. “It was like zero-to-sixty,” he said. “One minute I’m in the mountains of New Hampshire, the next I’m sleeping on this guy’s couch in Union Square. My girlfriend of two years broke up with me. It was the first time I had been without a serious girlfriend in five years.”
Two weeks in, he was at a cafe when a vixen in her 30s took an interest in him. They shared a cocktail. She asked if he lived nearby. She moved differently than the girls he had been with before, and had tattoos. When it was done she got dressed. He had never done anything like that.
“I remember I was lying on the bed, staring up at the ceiling. She came over and kissed me and said, ‘Welcome to New York, honey.’ She left almost immediately after.”
Not long after that, he moved in with a 31-year-old Polish model in Greenpoint, Brooklyn. (A friend notes that Mr. Webb “tends to use the term ‘model’ liberally.”) That lasted three months, but long enough for Mr. Webb to start playing at the McCarren Park tennis courts and compete in the Fibak Cup, hosted by the Polish American Tennis Association. (He would go on to win the cup three years in a row, demolishing local favorites and often playing half-drunk, which did not endear him to the Polish community; he was banned from further competition.)
He moved to Soho, started smoking Marlboro Reds and discovered that he did not need sleep.
“Work made me look at time differently,” he said. “Because either you work 100 hours a week and go home and sleep, or you don’t, and I didn’t. I just wasn’t sleeping. I was sleeping two hours, one hour a night.”
At the end of the week, he and his pals would add up the hours each had slept in the previous five days. It would average about eight. He found he didn’t like to hang out with bankers outside work. Instead of going out for drinks with the boys, he’d go home, smoke a jay and call up his friend, New York Post gossip reporter Neel Shah, and tag along with him to ridiculous, open-bar media parties.
“It was insane,” Mr. Shah told me. “He was out just as much as I was, but he didn’t sleep. I can’t even count the number of times it would be 4 a.m. and he would be like, ‘Shit, I’ve got to be at work in two hours.’ I think he always felt kind of pigeonholed in the banker category. When we would be out, and people would ask, he would say, ‘Oh, yeah, I work in finance,’ and then he would shuffle off.”
In the summer of 2007, at a Goldman banquet lunch, Mr. Webb was given the award for least usage of his BlackBerry. He went up onstage and accepted it as the efficiency award. And indeed Mr. Webb was efficient. After two years as an analyst, his contract was renewed—many weren’t.
For Graham Kay, 27, a comedian, the story of Mr. Webb’s efficiency award “sort of sums up to me why I like him. He’s sort of the one black sheep. He beat the system—he made a lot of money and got out.”
They met through a mutual friend, when Mr. Kay was living in Budapest and Mr. Webb swept through town on a post-college jaunt through Europe.
“When I first met him, I hated him,” said Mr. Kay. “He seemed like a U.S. college fraternity boy, Wall Street dumb-ass. The kind of kid who would only care about money, and all the things I despised.”
Mr. Webb thought Mr. Kay was a fancy boy who used too much hair product and had a bizarre way of walking in which he moved his shoulders violently back and forth, which brought to mind a shapely woman walking down Fifth Avenue. When both had settled in New York, they became friends.
Mr. Webb met a more highbrow friend while having lunch at Whole Foods a few years back, when he began rapping out with the gentleman sitting next to him, Peter Pazzaglini, a 64-year-old philosophy professor at Columbia University. They exchanged emails. Since then Mr. Webb has been slowly making his way through Mr. Pazzaglini’s syllabus. Every couple months they meet.
“I have observed him to be a person of high native intelligence, integrity, authenticity and transcendence,” Mr. Pazzaglini told me over the phone. “I’ve seen those qualities grow. He is interested in learning about the ways of knowing. And is not afraid to ask the great questions: Who am I? How do we become who we are? I have always told him, ‘Follow your heart. There’s an acorn embedded within you.’ David is on the journey of Parsifal.”
Last summer, Mr. Webb was promoted to an associate position at Goldman. This, it seems, was as far as Mr. Webb had intended to climb. Like making it to the finals against Johnny Chu. He had played lights-out.