Illustration by Andrew Bannecker

On a summer day in June of 2005, a young, pretty elementary school teacher named Allison walked into the Wireless Café at the corner of Lexington Avenue and 74th Street. The store, cozy and informal, offered cacti in the window and an international cast of good-looking young men behind the counter.

It was located around the corner from the private school where Allison taught the first grade. School had just let out for the summer. In a few days, Allison would be leaving on a summer-long education trip that would take her from Iceland to the French Riviera and countless spots in between.

She needed a cell phone that would work overseas. She had chosen the store based on a recommendation from her mother, who claimed that practically every woman on the Upper East Side had purchased her first cell phone there.

Allison bought a fancy phone, which she believed would work in the middle of the Mediterranean if such an emergency should arise. She took it home and out of the box, and discovered to her dismay that the instructions were in German. So she returned to the Wireless Café. This time, she bought a BlackBerry. Again, there were problems. She was standing at the counter, worrying about her trip, and frustrated beyond belief.

That’s when she began chatting with Andre Roper.

In a small store like the Wireless Café, Roper was hard to miss—a gregarious man of enormous stature, roughly six feet three inches and 300 pounds, with an even bigger personality. He wore a Marc Jacobs purse and hot-pink sunglasses. At times, he stood behind the counter, helping customers. Other times, he focused his attention on entertaining a gaggle of teetering teenage girls who were hanging out in the store. They looked to Allison like girls she could have gone to high school with. They were young and cute and preppy and enraptured byRoper’s every word.

Roper told Allison that he loved her shoes and that she was fabulous and gorgeous

and how did they not know each other? Allison explained to Roper that she was raised on the Upper East Side. She had gone to Dalton and then to Duke for college. Roper told Allison that he was out on summer break from Wesleyan and living in a ridiculous duplex on Park. His dad had made him get a summer job. Can you believe it? Roper began tossing out the names of his famous friends who had also gone to Dalton.

The more Allison listened, the more she began to think that Roper belonged on television. He was like a character straight out of MTV’s My Super Sweet 16, if he weren’t a 300-pound black man.

He was also pretty damn good with cell phones. Soon, with Roper’s help, the BlackBerry was working. She thanked Roper and prepared to head home to Union Square to finish packing. Roper offered to split a cab with her. He was headed downtown, too.

During the cab ride, Roper showed Allison how to use her BlackBerry, and they kept chatting. Roper confessed that he too wanted to become a teacher. Not a lot of people from the Upper East Side want to be teachers, Allison thought. This guy was really great.

Soon, she was opening up. By the time the cab reached her apartment building, she had a new friend. Before she got out of the cab, Roper invited her to a killer party he was throwing in

the Hamptons. She declined, explaining that by then she’d be far away on a boat in the middle of the ocean.

A few days later, Allison was in Halifax when her BlackBerry rang. It was her first call since leaving New York.

She recognized Roper’s voice right away. Again, Roper invited her to his party that night. Again, she declined. The whole thing was kind of strange, Allison thought. Hadn’t she told Roper that she was going away? Well, whatever.

A few weeks later, she was in Iceland when the BlackBerry buzzed again. This time it was her parents. They were upset. Allison’s dad owns a consulting company that employs two company drivers. Now her parents were demanding to know why she had given permission to her friend—Lauren, maybe?—to call the drivers for personal rides. Allison told them that she had done no such thing. Must be some sort of mix-up.

In early July, Allison’s older brother Lawrence received an odd phone call. The young woman on the other end of the phone introduced herself as Lauren and explained that she was a close friend of his sister’s. Lawrence was in Toronto at the time. In a few weeks, he would be relocating to New York. Lauren wanted to know if Lawrence needed any help moving to the city. Did he need the name of any good nightclubs?

Lawrence, who has a young son, told Lauren that he wasn’t much of a rager. The more Lauren kept talking, the more Lawrence felt confused. She kept referring to his sister as the “Visa Queen.” The Visa Queen? That didn’t sound much like his sister, the earnest elementary school teacher.

Before they got off the phone, Lauren asked if he knew when exactly he would be staying at Allison’s apartment over the summer. Lawrence told her the dates.

A few weeks later, Lawrence arrived at his sister’s 20th-floor apartment in a luxury building near Union Square. His sister’s weird friend Lauren was nowhere to be found. In the meantime, Lawrence was left to clean up his sister’s apartment. She had left the place a mess.

The floor was dirty. There was a cake in the fridge and lots of beer—not to mention a bag of devices that looked like a bunch of gas masks. (Maybe in case of a terrorist attack?) On the floor of the apartment’s bathroom, there was some shattered glass where a framed poem had fallen off the wall. Lawrence didn’t spend much time inspecting its stanzas. If he had, he might have noticed that the poem, written years earlier as a present to his sister from a friend named Lauren, had made a joking reference to her as the “Visa Queen.”

But Lawrence didn’t notice. In fact, nothing in the apartment seemed so out of place as to arouse his suspicion. His sister had never been the cleanest person in the world.

Toward the end of July, Allison was in Monaco when she received one more unexpected phone call. It was a representative from her bank in New York, calling with bad news: Her bank account was overdrawn by approximately $20,000.

Allison was flabbergasted. She had never been that great with finances. Maybe she had mixed up the exchange rate on the euro?

When Allison returned to New York during the second week of August, her boyfriend, David, a tall, handsome 24-year-old Upper East Side native, met her at the airport. With Allison back, her mom was throwing a family reunion at their house in Quogue, on Long Island. The plan was to head back to Allison’s apartment, repack, and head for the Hamptons.

Back at the luxe apartment, David took a seat at Allison’s desk. There he noticed an odd-looking bag. He opened it and discovered a handful of oxygen masks like the ones football players huff into on the sidelines during games. One of the masks was decorated with a dinosaur sticker.

David called Allison over and they stood looking at the masks. Then Allison wheeled around and took a hard look at the apartment. In a flash, she realized that something was wrong. Things were missing.

Her stereo speakers were gone. Her top-shelf liquor had been replaced with cheap stuff like a bottle of Parrot Bay rum. In time, she would notice other missing items, including an iPod, two watches, her college ID, the keys to her parents’ house on Long Island, and on and on. Also missing was a rectangular sheet of laminated paper that Allison’s parents had made for each member of the family, containing their e-mail addresses, their cell phone numbers—and those of the company drivers.

David and Allison marched downstairs to confront the building’s managers. When pressed, one of the managers had a simple answer: “Your brother has been throwing some crazy parties.”

Allison retorted that they must be mistaken. She explained that her brother wasn’t the type. They asked if she had a picture of him. Allison raced upstairs and returned with a photo.

The building managers looked nervous. Finally, they began describing to Allison the guy they thought was her brother or maybe her brother’s boyfriend—big, black, flamboyant, charming, extroverted, used the concierge service constantly.

Immediately, Allison knew who they were describing. It was Andre Roper.

Following the revelation, Allison called the owner of the Wireless Café and began laying into him. She demanded information on Roper. The owner of the store gave her Roper’s cell phone number, told her not to call again, and hung up. (The owner failed to return several requests for comment.)

After calling the police, David and Allison went down to the Ninth Precinct Station House on Avenue C to meet with detectives about Roper.

As it happened, the cops already had a file on him. Despite being only 21 years old, Roper had already racked up a string of criminal offenses ranging from unauthorized use of a vehicle, to possession of stolen property, to “illegal diversion of lab equipment by overseer.” He had been released from prison only a few months before meeting Allison.

The cops put together a photo lineup. Allison picked out Roper. Then she and David left for the Hamptons.

When they returned from Quogue a few days later, the police still hadn’t arrested Roper.

In the meantime, an unpaid bill from Bloomingdale’s had arrived in Allison’s mail for $1,874.70. Apparently, Roper had gone on a shopping spree using her Bloomingdale’s credit card. Allison also soon realized that her overdrawn bank account had nothing to do with, say, extravagant meals in Monaco. Her checkbook was also missing.

In a fit of anger, David decided that he would try and catch Roper himself. He picked up the phone and punched in the number that the Wireless Café owner had given Allison. The call went to voicemail. David left a message.

A few minutes later, somebody named Lauren called back and demanded to know how he had gotten her number. By now, David had talked extensively with Allison’s brother about his interaction with the mysterious Lauren, and he was convinced that Lauren was, in fact, Roper, sounding like a woman. David decided to play along.

He told Lauren that they had friends in common; did she want to meet up sometime? Lauren explained that she was the little sister of celebrity publicist Lizzie Grubman and that she was currently in London. Later, she bragged to David about her fabulous going-away party at Rock Candy, a nightclub on East 21st Street, where Lauren and her friends had racked up table service to the tune of four bottles of champagne and three bottles of vodka.

As it turned out, David knew the owner of Rock Candy. When the conversation ended, he called his friend and asked whether they had hosted a party recently, featuring a 300-pound black man and an entourage of young white girls? The owner checked with his manager. Sure enough, there had been a party fitting the description.

Over the next few days, David tried to lure Roper back to New York by inviting Lauren to a party at Rock Candy. When that didn’t pan out, David invited Lauren to the MTV Video Music Awards, to which he had an extra ticket. But Lauren wouldn’t take the bait.

On Wednesday, August 31, Roper arrived at JFK Airport on a transatlantic flight from London. He had flown first-class, and on the ride home, he allegedly traveled in comfort, taking two chauffeured vehicles: one for himself, one for his luggage.

Following Roper were detectives from the Ninth Precinct. After midnight, Roper’s cars arrived outside the Ritz-Carlton—where he was about to move into an apartment on the 34th floor. The detectives approached him outside the building, and Roper fled on foot. But he wasn’t in the best of shape. Soon the cops caught up with him. Back at the station, in the quiet moments before dawn, Roper confessed.

“I went to her apartment and told the doorman I was her brother,” Roper told the detectives. “The doorman gave me the key. I hosted six or seven parties at her apartment. There were about 50 to 60 people at the parties and I charged $20 a person.” He also confessed to taking Allison’s checkbook and Bloomingdale’s card.

At the time of Roper’s arrest, the police had found in his possession a photocopy of a credit card belonging to someone named Matthew Bloom. They began a parallel investigation.

The following morning, detectives called and asked Allison if she could come down to the station. At the precinct, Allison peered through a one-way mirror and saw the outsize charmer from the Wireless Café curled up on the floor in the fetal position. Allison learned from the detectives that Roper had apparently been documenting his fabulous summer using her video camera. Until then, she hadn’t even noticed it was missing.

Roper was soon released on bail. About a month or so later, the cops picked him up again. Back in custody, Roper played the role of an entitled, neurotic, Jewish teenager. “I can’t believe you’re arresting me on Yontiff,” he told the officers. “I was off my medication.”

In the months to come, with the case preparing to go to trial, Allison met up with an assistant district attorney to witness the videos that Roper had made on her camera. Allison sat down and watched in horror as throngs of preppy teenagers were shown stumbling around her living room, slurping down mixed drinks, smoking pot, and inhaling nitrous oxide through the gas masks. At one point, the various partygoers stood in front of her closet, looking through her clothes, and commenting on the designer labels.

There was also a short scene that captured Roper at an apartment with his actual mom. But the glimpse of Roper’s home life was fleeting. Not enough to answer the question that would still be puzzling Allison more than a year later.

Who was Andre Roper?

During the fall of 2005, Allison wasn’t the only person pondering Roper’s past activities. At around the same time, a detective with the U.S. Department of Homeland Security was also trying to untangle Roper’s world.

On November 29, the detective got a phone call from employees of JPMorgan Chase Bank in Brooklyn. They were concerned about some suspicious wire activity.

About three weeks earlier, the bank employees had noticed a transfer of $500,000 from a titling business headquartered in Brooklyn called the Avalon Abstract company into Roper’s personal account. A bank investigator became suspicious, froze the money, and began sifting through past records. On August 29, $150,000 had been transferred from Avalon Abstract into Roper’s account. Toward the end of September, it happened again. Another $700,000.

How had Roper managed to steal close to a million dollars from an obscure company in Brooklyn?

The detective soon discovered that on August 29, Roper had called a Chase branch in Pelham, New York. Somehow Roper had obtained Avalon Abstract’s account number. Over the phone, from London, he had given the number to a teller while pretending to be an employee of the company’s president. Using his outsize charm, Roper had then talked the teller through the transaction.

At the time, Roper was hardly loaded. His account showed a negative balance of $441.42. By the end of the business day, he was flush with cash. Shortly after the transfer, Roper paid $51,800 for the one-year lease on the swank apartment in Battery Park City.

Following his arrest, Manhattan prosecutors indicted Roper in the fall of 2005 on a range of charges, from grand larceny to burglary to forgery. Eventually he pled guilty and received three to six years in one case and six years in the other. Additionally, in April of 2006 the federal prosecutors indicted Roper on a felony charge for defrauding the Avalon Abstract Corporation. In September of 2006, he pled guilty in that case too.

By the time I heard of Roper’s case, he was living in a Brooklyn jail cell, south of Park Slope near the Gowanus Bay, awaiting his federal sentencing hearing. I wrote Roper a letter requesting an interview. He agreed. And on a Wednesday afternoon in mid January, the jail’s assistant warden put Roper on the phone.

Roper’s voice surprised me. He didn’t sound like a big, burly man of Jamaican descent. He sounded more like a jaded teenager from the North Shore of Long Island.

Over the next hour, Roper proved to be preternaturally charming, quick-witted, and encyclopedic about New York society. He also demonstrated a tentative grasp of what is real in his life and what is fantasy, mixing the two seamlessly throughout the conversation.

Roper explained that his problems that summer began when he dropped his cell phone on the way back from the Equinox gym on East 85th Street. Afterward, he said, he stopped by the Wireless Café to fix his phone. Soon he had a job. Shortly thereafter, he met Allison.

Roper claimed that he grew up in Greenwich, Connecticut, attended Phillips Academy, Andover, and went to college at New York University, where he undertook an interdisciplinary major in life skills, which included internships at Goldman Sachs and the French embassy. When Allison came into the store, he said, he spotted a fellow member of his peer group. Pretty soon they were talking up their mutual connections, including a friend they had in common from Allison’s synagogue.

“When people live on the Upper East Side and in Greenwich, a lot of people go to private school, and boarding school, and similar summer camps,” said Roper. “So people are bound to know each other through different people. It wasn’t like I stalked her or something. She went to Dalton and Duke. Do you know how many friends I had that went to Dalton and Duke? She was a Tri Delta. My sister is a Tri Delta. You know what I’m saying?”

Why did he take her apartment?

“It’s summer time,” Roper said. “Kids are still in the city. They’re either working for their parents or just going back and forth to the Hamptons. I needed a place to have parties. I figured, well, she’s not home. She wouldn’t even notice.”

According to Roper, convincing the doormen that he was Allison’s brother was easy and nobody even asked to see his ID. “No one said anything to me,” said Roper. “What are they going to say to me? I’m not a little guy.”

Roper said that at some point he began running out of money, which was when a guy named Matthew Bloom walked into the Wireless Café. Roper said that he didn’t like Bloom from the get-go. “He was just such a pompous Australian prick,” he said. “I’m partially British. I just hate Australians.” (Bloom did not return several phone calls seeking comment.)

Using the Wireless Café’s copy of Bloom’s driver’s license and his American Express number, Roper went on another mini shopping spree. At the time, Roper was looking to get away from the city. So he purchased a round-trip, first-class plane ticket to London on Virgin Atlantic and charged it to Bloom’s credit card. The total cost was $8,547.28. He also used Bloom’s card to pay $1,874.70 in vet services for his dog Romeo, a white Labrador with blue eyes.

“Beautiful, beautiful dog,” Roper said.

Roper told me that London is practically his second home. At first things were great, but then he began running out of money again. That’s when he dreamed up the scheme involving Avalon Abstract.

How did he do it?

Roper explained that when he was living in New York he made the acquaintance of the college-aged son of the woman who owns Avalon Abstract. (Several calls to the company’s offices in Brooklyn seeking comment were not returned.)

“One day we were at this place called Mamoun’s, which I eat at religiously because I’m Jewish, and I love falafel,” Roper said. “We were sitting there and he was like, ‘You know what happens when I go to Chase Bank, I get respect. Because all of my mom’s accounts have at least $5 million in them.’ ”

“He’s one of those,” Roper said.

According to Roper, he kept asking more and more questions until eventually he knew the ins and outs of the business. Roper said that when he was sitting in London, pondering his dwindling funds, he dreamed up the embezzlement idea.

How did he fool the bank tellers?

Roper was circumspect. “I’m telling you, you’re going to bug out,” Roper said. “All I did was call a branch and ask for a guy who handles all their business accounts. I said that I worked for Avalon and [president] Armando Berrios. I told him, ‘Armando told me to transfer $150,000 from this account into this account.’ He said, ‘OK, fine.’ I was in London when I did this. Within 15 minutes, it was cleared into my account.”

Roper contemplated staying in London. But eventually he returned to New York. After all, he had his new apartment to look forward to. “Who doesn’t want to live in the Ritz- Carlton?” said Roper. “It had water views and views of midtown. It was on the 34th floor. I can’t live below the 20th floor, especially in Manhattan. You never see anything.”

Looking back, Roper said that the whole situation could have been avoided if he hadn’t suffered through a falling out with his father—Lawrence Roper of Sands Point, Long Island. According to Roper, if he had stayed on good terms with his father, he never would have fallen into such desperate financial straits.

Toward the end of the interview, Roper confessed that he’s had a hard time coping with his own mental illness in jail. “I take lithium twice a day,” he said. “I’m bipolar. I’m not getting the mental health I need . . . I was seeing a therapist three times a week.”

“Here it’s nothing,” he went on. “This place makes you constantly paranoid. The majority of the people I’m around are like the violent drug dealers and gang members and stuff like that. They’re like the proletarians.”

After the interview, I spent several days fact-checking Roper’s story. In the end, most of what he’s told me about himself turns out to be false.

No public records indicate that he ever lived in Greenwich. According to officials at Phillips Academy, Andover, no one named Andre Roper ever attended school there. No public records suggest the existence of a Lawrence Roper living in Sands Point. Other biographical details don’t check out.

So where is Roper actually from? Eventually I discovered that Roper has a mom and a sister who live in Flatbush, Brooklyn.

On January 31, I knocked on the door of his sister’s fourth-floor apartment in Flatbush. Roper’s mom invited me in. She was dressed in a green T-shirt, baggy cotton pants, and orange slippers with yellow flowers. Originally from Jamaica, she told me in a lilting accent that she works as a nurse aide and is currently babysitting her grandson—a friendly, young kid, who is zipping around the apartment occasionally flashing a big, winsome smile.

We sat down in the living room, which is decorated with Roper’s sister’s wedding photos and strewn with his cousin’s toys. The moment I brought up Andre, his mom began crying. Over the next hour, she told me that Andre was born in Brooklyn. The family then moved to East Orange, New Jersey. In East Orange, all of Andre’s teachers said he was exceptionally smart. But he never graduated from high school. “His teachers used to say that Andre could be anything that he wanted to be,” she said. “He made bad choices.”

Andre first started seeing a therapist as an adolescent and was subsequently diagnosed as bipolar. “Andre is a good person,” his mother said. “He’s been in and out of mental institutions. But he’s not going to hurt anyone.”

Does she know when Andre became so seemingly obsessed with wealthy New Yorkers? “It started with his mental problems,” she said. “I don’t know why.”

Andre does fine when he takes his medication. When he stops, things go haywire. For many years, her health insurance helped pay for Andre’s psychiatric costs. But during his most recent stint out of jail, he was seeing a therapist who wasn’t covered under her plan. Andre was doing well, the therapist had told her. Looking back, she thinks it was a waste of money. “I think Andre was outsmarting her,” she said, “How could she not know?”

Like everyone else, she remains baffled by Andre’s crimes. “He’s a charmer,” she said. “Everybody loves Andre.” Even so, she can’t figure out how Chase Bank could have let him steal all that money. “So he just walks in and said he’s Donald Trump and they believe him?” she said. “I think that Chase Bank should be the ones on trial, they’re so stupid.”

I asked if she will attend her son’s final sentencing hearing. She said no, it would be too painful. But she will be thinking of him. “I pray every day,” she said, “that Andre will change.”

In mid January, Roper’s lawyer submitted a sentencing memorandum on his client’s behalf. Over the course of several pages, the lawyer reported on the findings of the court-appointed doctor—noting, along the way, that Roper suffers from bipolar and borderline personality disorders as a result of being “shunned, beaten, and sexually abused” as a child. “He lives in a fantasy world and has dramatic mood swings including suicidal ideation,” wrote the lawyer. “His crimes are just another way he has learned to use to hurt himself.”

Offsetting those problems, the lawyer argued, is the fact that Roper is highly intelligent, and “clever in the extreme.”

“In [the doctor’s] opinion, hospitalization is not now needed, but intense therapy and medication is,” concluded the lawyer. “The defendant is likely, it is reported, to improve with therapy, licit drugs, and maturity.”