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How to Hide $400 Million


A few weeks after she realized her husband was finally leaving her, Sarah Pursglove flew down to the Bahamas to figure out how much money he really had. Like many women married to very wealthy men, she didn’t know much about the family accounts. Her husband, a Finnish entrepreneur named Robert Oesterlund, had sworn to a Canadian court that his immediately calculable “net family property” totaled just a few million dollars. Pursglove was skeptical. She could come up with several family purchases worth more than that off the top of her head. There was the 165-foot yacht, Déjà Vu — that cost a few million dollars a year just to keep on the water. There was the $30 million penthouse at the Toronto Four Seasons, which was still being renovated. It wasn’t their only home. The Déjà Vu wasn’t even their only yacht.

Pursglove grew up in a working-class family. She did not consider herself to be a complicated person, or a greedy one. Recent events in her life had, however, inculcated a newfound habit of suspicion. Her husband’s tirades, his frequent absences and threats to leave, had led inexorably to the day when she tailed him through the streets of Toronto and caught him picking up an interior designer for what appeared to be a romantic ski getaway. She had been with Oesterlund since she was 25 and scraping by as a cruise ship’s photographer. Now, as she assessed her crumbling marriage and girded for divorce, she wondered what else she didn’t know.

Her first answers came that morning in the Bahamas, as she quickly rifled through papers in their soon-to-be-former vacation home. She didn’t have long: The caretaker, Pursglove suspected, was loyal to her husband and would soon alert him that she was there. In a pile of mail was a statement from a bank in Luxembourg showing an account with at least $30 million in cash. She had never seen it before. There were two laptops — one with baby photos of their younger daughter, which she set aside. In a cupboard were documents concerning not only Xacti, the internet company she and Oesterlund had built, but also oddly named corporations in other states and countries. Finally, there was a statement from their accounting firm. She had never seen that before, either. The accountants seemed to think her husband was worth at least $300 million.

But even as Pursglove was repacking her suitcase for the flight home, her family’s fortune was vanishing into an almost impenetrable array of shell companies, bank accounts and trusts, part of a worldwide financial system catering exclusively to the very wealthy. In recent decades, this system has become astonishingly effective at “offshoring” wealth — detaching assets, through complex layers of ownership and legal planning, from their actual owners, often by hiding them in another country. Created by lawyers, accountants and private bankers and operating out of a global archipelago of European principalities, former British colonies and Asian city-states, the system has one main purpose: to make the richest people in the world appear to own as little as possible.

Pursglove would soon learn, however, that navigating this offshore archipelago is not easy. In any given year, trillions of dollars sit safely in the offshore financial world, effectively stateless, protected by legions of well-compensated defenders and a tangle of laws deliberately designed to impede creditors and tax collectors. Even the United States government finds it challenging: A special Internal Revenue Service division known as the “wealth squad,” set up in 2010 to crack down on high-end tax evaders with multinational holdings, today has enough manpower to assess only about 200 cases a year.

Pursglove would rely on her own wealth squad: a pair of highly creative lawyers, using Pursglove herself as the ultimate informant. It would take them more than two years and millions of dollars to breach the defenses of the offshore financial world. Their efforts would leave a trail of thousands of pages of court documents through Canada and the United States, revealing the inner workings of a system exquisitely engineered to repel scrutiny.

But much of her family’s financial situation was still a mystery when she first saw the bank statement on her husband’s desk in the Bahamas, Pursglove later told me. She packed the laptop and documents, left her suitcase near the front door and went for one last walk on their beach. When she returned to the house, the caretaker was nowhere to be seen. A different member of the household staff, a kindly older man who tended to the landscaping and washed the family boats, had already put her suitcase into a waiting taxicab. She hugged him goodbye and drove to the airport.

When she opened her suitcase at the security line, there was no laptop. No paperwork. It was all gone.

Robert Oesterlund wasn’t born rich, either. When Pursglove first met him, on a cruise ship off Helsinki in the ’90s, he ran a struggling flower-import business. He was tall, with piercing blue eyes and a boyish charisma that outlasted his initial awkwardness. Pursglove, who grew up in Wales, found him charming. They married in 1998, on the Caribbean island Dominica, and settled in the United States.

Living in Florida and New York, they started a series of companies. Oesterlund came up with most of the ideas, Pursglove would later state in court filings, and ran the companies day to day. Pursglove hired the employees, trained them and helped manage the offices. Their earliest success was a direct-mail firm called Credit Key Express, which promised credit cards to people with bad credit. Later they started Columbia House-style online membership clubs that sold discounted movie posters, books, DVDs, even dietary supplements. Xacti, which came to enfold most of their ventures, sold banner ads, video games and various other kinds of software, including “toolbars” that promised to clean viruses off your computer or free up space on your hard drive. The businesses threw off enormous amounts of cash, and by the mid-2000s, Oesterlund and his wife had become wildly rich. They bought a $5 million house back in Finland and their first yacht, a 48-foot cruiser.

Pursglove is 47, with a round, watchful face and well-kept brown hair. I first met her in the spring of 2015, over coffee in New York. She rarely smiled, and I found her unexpectedly reserved for the wife of a jet-setting, large-living entrepreneur. She explained that Oesterlund was the flamboyant one, an insecure man ruined by his sudden wealth. “I was his stop button — ‘No, we don’t need it,’ ” Pursglove told me. “He was kind of never content. He always needed to buy the next thing.” In 2007, they bought their first private jet, and then a bigger boat, an 82-footer that Pursglove named Integrity. She liked the name, she explained. “At the time, Robert was — I thought he had integrity.”

Not everyone agreed. In 1999, the Florida attorney general sued to shut down Credit Key Express, saying that it misled customers into thinking they would receive preapproved credit cards. (In fact, all they got for their money was a list of banks that might give them credit cards.) Some years after Credit Key Express shut down, the Florida attorney general came after Xacti’s club businesses, claiming that Oesterlund’s companies had again misled customers. According to court filings, they had abused what are known as “negative options”: Customers would provide their credit card number for a “trial offer,” only to be charged a monthly fee, disclosed in the fine print and difficult to cancel.

In 2010, Oesterlund, on behalf of his companies, signed an agreement with the Florida attorney general promising to abstain from deceptive marketing practices. But officials in Iowa and Oregon also began scrutinizing the businesses. Despite Oesterlund’s promises, consumer complaints continued to pile up, and in 2013, Florida’s attorney general finally sued Xacti and its club businesses, extracting a $500,000 settlement.

When the investigations began, in 2009, Pursglove was living with the two children in Boca Raton, but Oesterlund lived on Integrity in the Bahamas, unable to join them. He had overstayed an earlier visa, and the United States denied him a green card. The denial and the investigations enraged him, Pursglove told me. He employed dozens of people in Florida, he fumed, and had provided the United States millions of dollars in tax revenue. He told his wife their businesses were being unfairly harassed by bureaucrats. Going forward, Pursglove explained, “he wanted to pay as little taxes as possible to the U.S.”

In 2011, they went into contract on the penthouse in Toronto, hoping to unite the family eventually in Canada and establish residency for Oesterlund there. While it was being renovated, they bought yet another boat, the 165-foot yacht they named Déjà Vu, and spent a year sailing around Europe and the Caribbean, with tutors for the kids. But their relationship would soon grow strained. Oesterlund later testified that their marriage was a “rocky ride ever since the start,” but Pursglove blamed their new lifestyle. Somewhere along the way, she told me, Oesterlund had fallen in with a tribe of wealthy globe-trotting nomads and minor celebrities. He befriended Kevin O’Leary, a judge from “Shark Tank,” she says, and partied at the Maya-themed Lyford Cay estate of Peter Nygard, the Finnish-Canadian retail mogul. Oesterlund’s money and his boat attracted hangers-on and women, Pursglove says.

By his wife’s account, some of Oesterlund’s new friends also began tutoring him in how to minimize his taxes. (Oesterlund himself declined to comment for this article, as did most of the lawyers, accountants and financial advisers named in court records.) He traveled constantly, Pursglove says, in part to reduce the amount of taxes he would be required to pay to any of the countries where he owned a home. At the time, Pursglove told me, she regarded these efforts — spearheaded by a well-known Florida accounting firm, Daszkal Bolton — as aboveboard “tax planning.” But court records suggest that Oesterlund had begun exploring how to structure his business to insulate himself not just from taxes but also from future civil litigation. “I want to have in writing a statement,” he wrote to his lawyers in 2011, “that I can no longer be subject to Florida or U.S. law.” Take every step necessary, he added, to “remove myself from the country of Evil.”

In 2012, Oesterlund and Pursglove moved with the children to Toronto; at the end of the year, Oesterlund raised the idea of separating, Pursglove says, and at the beginning of 2013 he flew to Dubai to party with friends. “He was backward and forward that year in Toronto,” Pursglove says. “I would ask, So, are we getting divorced? And he wouldn’t do anything.”

It was in early 2013, when she learned that her husband had sought to sell off Xacti, Pursglove told me, that she started to think about hiring lawyers of her own. “You want to throw me away like I was a piece of [expletive] and then take everything too,” she emailed him one night.

“Women get 10 percent in Russia by law,” Oesterlund wrote back. “In Dubai they get 0 percent.”

When she asked for copies of documents related to the potential sale, her husband was livid. “I am closing out all checking accounts on you now,” he texted her. “You aren’t going to use my funds to pay some Jewish lawyer.”

That night, he cut off her Xacti email account. “We will file papers and as I no longer own anything of value you get nothing then I can start a new company later in life,” he wrote. “Was it really worth it?”

One divorce attorney urged her to settle with her husband as soon as possible or else risk losing everything. Another told her the case would be too daunting for a normal family lawyer, even in South Florida, where high-priced divorces are common. Eventually, she found herself in the offices of Jeffrey Fisher.

Fisher was not a normal family lawyer. Early in his career, at the height of the South Florida drug wars, he worked for the United States attorney’s office in Miami, prosecuting cocaine smugglers and money launderers. When he opened his own firm with a partner in West Palm Beach in the late 1980s, he began specializing in cases that were equal parts divorce and white-collar litigation, representing the discarded wives of rich men with complex business concerns.

I first began hearing about Fisher a few years ago, when he approached a college friend of mine, Zachary Potter, to join his practice. Potter was working at one of the country’s largest law firms, advising Fortune 500 companies. He enjoyed the challenge, but the work could be stodgy: When Fisher called him, Potter was working a seven-year, $100 million case that hinged on federal leasing rules for long-haul trucking companies.

Credit Illustration by R. Kikuo Johnson

Around the same time Potter moved to Palm Beach to join Fisher’s firm, I began writing for The Times about the political activism of the very wealthy, much of it oriented around defending their fortunes from the predations of government. Our professional interests soon converged. We joked about spending our days trading phone calls with the same class of handlers, consultants and lawyers, hired by the rich to guard their wealth and privacy.

One day last year, we caught up over drinks at a Palm Beach hotel. Potter was easy to spot: In a town of pastels and prints, he still favored charcoal suits and crisp white shirts. All around us was the chatter of lithe women and their expensively tailored, somewhat older male companions — inhabitants of a world at once ostentatious and opaque. As we sat down, Potter slid a neatly stapled stack of papers down the bar toward me. It was a court brief, Potter explained, one of hundreds he and Fisher had filed in a particularly knotty case involving a man named Robert Oesterlund. If I truly wanted to peer inside the hidden world of the superrich, Potter told me — and if I really wanted to understand how extremely wealthy people protected that wealth — I ought to read the case’s public court file and judge for myself.

Not long after, I met Fisher at his office in Florida, a modest fourth-floor space equipped with plush leather chairs and a sweeping view across the water to client-rich Palm Beach. At 61, Fisher is short and wiry, with thinning gray hair swept back over a high and gently tanned forehead. In a cross-examination, he stands erect, chest cocked, as if to fill the courtroom. When Fisher talks about working the Florida divorce circuit, he makes it sound almost fun. “The beauty of high-end divorce law it is that it is usually handled on an expedited basis,” Fisher says. “If you’re a person like me, who doesn’t want a five-year-long case, there’s nothing better.”

Pursglove hired him about a year earlier, not long after seeing her husband with the interior designer. Oesterlund responded by filing for divorce in Canada — where Fisher could not personally represent Pursglove — and threatened to cut off his wife. She had $90,000 in the bank, not enough for a protracted legal battle. But she also had cellphone pictures of documents concerning something called a Cook Islands asset-protection trust, which she found a few months earlier. Oesterlund was listed as the “settlor,” the person who “donates” property to a trust.

The Cook trust was a bad sign. A typical estate-planning trust is designed to allow someone to benefit from a property — a car, a home, a plane, a bank account — without technically owning it or controlling it. An independent trustee, sometimes an individual, sometimes a specialized firm, is assigned to make decisions about the best use of the assets. That independence can, for example, provide a tax advantage or prevent a spendthrift beneficiary from plowing through an inheritance. But in some cases, the claim of independence is a sham. The trustees are puppets; the settlor still controls the asset in practice. And trusts organized in the Cook Islands, a self-governing state associated with New Zealand, are particularly difficult to investigate. Cook courts typically do not recognize American court orders, including divorce judgments. To sue a Cook trust, you have to actually fly to the Cook Islands, in the middle of the South Pacific, roughly 6,000 miles southwest of Florida. “It’s like Switzerland used to be, but squared,” Fisher told me. Once assets were hidden inside a Cook trust, he had learned, it was almost impossible to get them out.

Emails in Pursglove’s possession hinted at why Oesterlund might have found a Cook trust appealing. Searching through the trash folder on Pursglove’s laptop, Fisher’s paralegal found that the 2011 email she had been copied on — the one in which Oesterlund had asked his lawyers to remove him from “the country of Evil” — also contained a reply from Xacti’s corporate counsel, Jennifer Miller. She wrote that if Oesterlund created “a parallel corporate structure of companies outside the U.S,” moved his operations offshore and “implemented a personal asset protection strategy,” he could become almost untouchable. Any money spent to sue him in the United States, Miller assured him, “would probably be wasted.”

Fisher knew he needed to act very quickly. He didn’t know where Oesterlund had put the family’s money, exactly. He didn’t have any direct evidence of fraud. But the longer the case dragged on, the more opportunity Oesterlund might have to drain assets out of the country and into untouchable accounts overseas.

The documents in Pursglove’s cellphone pictures showed corporations in the Caymans and Nevis, both well-known offshore financial centers. But she didn’t know exactly what these companies did. Oesterlund had stopped making mortgage payments on the house in Boca Raton, she later said in court filings, and threatened to evict her mother and disabled aunt from a house they had bought in Wales. He warned Pursglove that he wouldn’t pay any bills until she agreed to a settlement. “Your mortgage of $20,000 was due on the first,” he texted to Pursglove. “Late fee $500 on Friday. Bad credit in 30 days. I recommend you pay it!”

Fisher had to freeze Oesterlund’s transactions in place until he could gather more evidence. The only way to do that, Fisher concluded, was to hit him from two sides at once. In late March 2014, Fisher filed a divorce action on behalf of Pursglove in Palm Beach County, hoping to wrest the divorce proceeding back to Florida from Canada. But he also prepared a related civil complaint, citing the Cook trust and Oesterlund’s threatening emails: Oesterlund, Fisher wrote in court papers, was using illegal asset transfers to defraud his wife, the co-owner of his companies. One set of claims would leverage Pursglove’s rights as a wife. The other, crucially, would leverage her rights as an owner.

Within days, Fisher persuaded a judge in Palm Beach County, Jeffrey D. Gillen, to impose a sweeping asset injunction against Oesterlund, one that prohibited him from selling, merging or borrowing against any of his assets. The order would stop additional offshoring — if Oesterlund complied.

Fisher also obtained a 2012 tax return for the family’s holding company, RSOP. (The name is an anagram of Oesterlund and Pursglove’s initials.) The return showed that RSOP had grossed more than $73.5 million that year, an amount that Pursglove says she found astonishing. But when Fisher scrutinized the tax return, he found something even more shocking. Despite the impressive grosses, RSOP was reporting ordinary business income of just $12,284. Virtually all the revenue had somehow evaporated.

That was when — and why — Fisher dispatched Pursglove to the Bahamas: to gather clues about where the money went. When Pursglove returned to the house to confront the caretaker that day, she told me, the caretaker admitted removing the papers from her suitcase. Bahamian police took custody of the papers, but later, and for reasons they never explained, handed them over to Oesterlund. When Fisher tried to subpoena the papers back, Oesterlund’s lawyers said he could not find any such documents; in any case, they wrote, Pursglove had no right to “stolen” materials.

Fisher was certain the privileged documents would contain a ‘smoking gun.’ He wouldn’t just see where the money was hidden. He would see Oesterlund plotting how to hide the money. The whole thing could be laid bare.

But back in Florida, Fisher’s legal blitz was having the intended effect. In a rush to unfreeze his assets, Oesterlund invoked his right to an emergency hearing. That handed Fisher a crucial opening: Florida law now gave Fisher the right to demand documents, on a highly expedited basis, from any company or person who might have evidence relevant to the hearing. Shortly thereafter, Fisher’s detailed requests began arriving on the desks of Oesterlund’s bankers, his lawyers, his accountants and tax planners, his stockbroker and most of his senior executives. When the opposing parties finally met in Florida court in April 2014, the room was overflowing. Oesterlund had sent his divorce lawyers. The companies had their own lawyers. There were lawyers for the banks. There were lawyers for the accountants. Even some of the lawyers had lawyers.

More important, some of these lawyers had brought thousands of pages of records with them to the hearing. Under normal discovery rules, Fisher might have spent months or years fighting for them. Instead, it took four days: Potter flipped through the boxes in the courtroom, yanking out whatever seemed interesting, while Fisher cross-examined witnesses on the fly. There were bank statements, emails between accountants and lawyers and a few organizational charts tantalizingly stamped “confidential.” One piece of paper, from a lender called Fifth Third Bank, showed that Oesterlund had claimed a net worth of $400 million, even more than they thought. Other documents showed that Pursglove owned a third of RSOP.

In Canadian court, Oesterlund accused his wife of making “wild accusations” and absconding with their two daughters to Florida. But Fisher now had a growing heap of evidence that not only bolstered Pursglove’s claims but also rooted them in the Florida jurisdiction where his client lived and he practiced. Seeing the danger, Oesterlund’s attorneys switched tactics, hoping to block the corporate fraud suit entirely and send Pursglove’s divorce back to a Canadian judge. She was a resident of Toronto, they argued to Judge Gillen, and a Florida court had no jurisdiction over the divorce.

For Pursglove and her husband, as for many members of the global 1 percent, “residency” was an elusive and easily manipulated concept. Pursglove was a British citizen with a United States green card who now lived in Boca Raton. Oesterlund was a citizen of Finland who had also obtained a passport from Dominica. They had homes in at least four countries and spent a year living on their yacht. “These parties are global citizens of substantial means,” Judge Gillen mused from the bench. “Their situation is a blessing and a privilege for them, but for this court, their lifestyle creates a challenge.”

Gillen decided to split the difference. The divorce would stay in Toronto. But the civil litigation — the corporate fraud lawsuit — could proceed in Florida, where many of the family’s companies were still run out of a Boca Raton office park. In late April, Fisher’s assistants began stacking boxes of files in the hallway outside his office. A similar pile grew next door, outside Potter’s office. In May, they started reading in depth.

First they searched for the missing $73 million they had seen on the tax return. It turned out that most of RSOP’s revenue wasn’t missing at all. Instead, Fisher later argued in court papers, RSOP was transferring tens of millions of dollars to another company, this one called Omega Partners. Omega was based in the Bahamas, which has no corporate income tax. RSOP had two partners, but Omega had only one: Robert Oesterlund.

Omega didn’t appear to have any employees. In fact, it seemed to consist of little more than a post office box in a government building in Nassau. But Omega did at one point have a lucrative contract with Oesterlund’s Florida company, Xacti L.L.C., to pay search engines to advertise his websites. This contract appeared to be an extraordinarily bad deal for Xacti. For every dollar of advertising Xacti purchased, it also had to pay Omega — Oesterlund in corporate form — 58 cents. For this privilege, Xacti also paid Oesterlund another $200,000 each month, personally, for “management services.”

Oesterlund appeared to be charging his own companies to pay their bills, Fisher argued in court papers. He was charging them so much, in fact, that RSOP was making almost no net income. Yet Omega was taking in millions of dollars a year. With the stroke of his signature on a few pieces of paper, it appeared to Fisher, Oesterlund had used Omega to make virtually all of his family’s United States tax liabilities disappear.

What Oesterlund had done is known as “transfer pricing,” a practice that has come under growing criticism in recent years. Multinational corporations use it to shift their costs to high-tax countries and their profits to low-tax countries. Often, there is little or no economic reality to these transactions. Apple, for example, is an American company headquartered in Cupertino, Calif. Most of the research and development that goes into an iPhone happens in California. But according to Apple, if you buy an iPhone in Europe or Asia, the intellectual-property rights contained in your phone actually belong to Apple subsidiaries in Ireland, where the company has negotiated for itself a special tax rate of around 2 percent. Apple charges those subsidiaries relatively little for the rights to this intellectual property, yet allows them to collect most of the money Apple makes from selling the phone. In 2011, the Irish subsidiaries — which conduct virtually none of Apple’s research and build few of its products — collected two-thirds of Apple’s 2011 worldwide pretax income.

Fisher wondered whether Oesterlund’s transfers were really legal. He called Gregg D. Polsky, a law professor now at the University of Georgia, who occasionally worked for Fisher as an expert witness. Polsky knew a lot about tax law, but as he later explained to me, he did not have a satisfying answer for Fisher. In theory, Polsky says, federal rules require that related companies charge themselves the same price they would charge some other company. But in practice, the prices can be difficult to second-guess. Who can really say exactly what Apple’s intellectual property is worth? “The sophisticated people will hire high-priced advisers who will come up with a study that will give them the value they want,” Polsky says. “The I.R.S. has to decide if they disagree with that value and if they can both challenge it and prevail in court.” (In August, European regulators ordered Ireland to collect $15 billion in unpaid taxes from Apple, charging that the company’s special tax rate violated European Union rules.)

Fisher didn’t have time to wait for the I.R.S. to take an interest in Oesterlund. He needed some other lever — a legal basis to look more closely into the myriad offshore entities that appeared to be connected to the Oesterlund companies. A solution presented itself when Fisher, searching online for Oesterlund’s name one morning, learned about the long trail of consumer disputes Oesterlund’s companies had left behind. Until he saw the settlement with the Florida attorney general, Fisher had assumed Oesterlund was running a basically legitimate internet business. Now he realized not only that Xacti had come under investigation, but also that the investigation created an opening for Pursglove. Oesterlund had signed a binding agreement with the Florida attorney general just nine months earlier: To keep Xacti from skipping out on refunds, the agreement barred Oesterlund from implementing “any change in the form of doing business or organizational identity as a method of avoiding the terms and conditions set forth in this settlement agreement.”

Fisher felt this was a pretty good description of what Oesterlund seemed to be doing with the offshore companies. Moreover, papers turned over at the hearing showed that Pursglove was the sole owner of an Xacti subsidiary that was subject to the same settlement. That meant Pursglove was also bound by its terms.

Credit Illustration by R. Kikuo Johnson

This gave Fisher an idea. In May, he opened a third front, one that would give Pursglove her most powerful legal tool to begin peeling back the layers of her husband’s finances. Intervening in the Florida attorney general’s dormant case, he claimed that Oesterlund had embroiled Pursglove’s company in a fraud against the people of Florida. The only way to stop it was for the court to drag the whole business — the Cook trust, the Nevis company and whatever else the court would let Fisher go find — back to Florida. To put it another way, Pursglove sued herself.

Oesterlund’s lawyers moved to toss this new lawsuit out of court too. Fisher thought he could become a kind of “private attorney general,” as he put it, pursuing Oesterlund for the public good. Oesterlund’s lawyers saw it differently. It was “unfounded, illogical, frivolous” for Pursglove to sue herself and her husband on behalf of the attorney general, they argued. Oesterlund’s personal lawyer, a veteran litigator named Gary Rosen, dismissed the lawsuit in court as “a leverage point” concocted by Fisher to pressure Oesterlund in the divorce. Oesterlund’s offshore trust was not an elaborate scheme to defeat the settlement, the lawyers argued, but the normal estate planning of a wealthy and successful businessman. And Pursglove, they said, was no victim. She had been part of her husband’s planning from the very beginning.

It was, in truth, hard to say where Pursglove’s involvement with the offshoring began and ended. In court filings, Oesterlund produced an email showing that on at least one occasion, Oesterlund’s advisers had discussed setting up a separate trust for Pursglove and for the couple’s United States properties. When I looked closely at the contracts between Xacti and Omega, I noticed that one of them bore not only Oesterlund’s signature, on behalf of Omega, but also that of Pursglove, on behalf of Xacti. She was also at one time a beneficiary of the Cook Islands trust, albeit only in the unlikely event that Oesterlund and both of their two daughters happened to predecease her.

Indeed, because Pursglove was a United States resident with a large ownership stake in several profitable United States businesses, she stood to pay far less in taxes if her husband could move the profits offshore. Moreover, both Pursglove and Fisher now stood to benefit from his new legal strategy: Lawyers are barred from working on contingency in divorces, but in the civil lawsuits, Fisher would be allowed to charge Pursglove a percentage of whatever money he could find and drag back to Florida.

Strikingly, Pursglove didn’t seem to have much sympathy for the consumers who had filed complaints against her family’s companies — the very basis of Fisher’s carefully plotted legal strategy. On more than one occasion, first during a long meeting in New York and later over a candlelit Italian dinner with Fisher and Potter in Delray Beach, I asked Pursglove whether she had any reservations about how she and Oesterlund had made their money. Whatever regrets she had about her husband, I learned, did not extend to the family business. “Every time you click on an ad, someone gets money,” she told me, shrugging. “We were the people who got the money.”

All this raised the possibility that Pursglove’s main objection to the offshoring scheme was that her husband had decided to cut her out of it. Oesterlund himself insinuated as much. “Wow your Jeff is desperate,” he texted her in May 2015, meaning Fisher, after a Canadian judge issued a further freeze of his assets. “Why would he want to expose you by trying to reopen the attorney general settlement? But ok we will throw you under the bus.”

Pursglove says she always knew Oesterlund was trying to minimize their taxes. But like many wealthy people who hire expensive help to execute complex tax transactions, Pursglove had considered herself to be avoiding taxes, not evading them — precisely the distinction wealthy people hire an accounting firm like Daszkal Bolton to observe on their behalf, however finely. Now, though, she was relying on Fisher to dismantle Daszkal Bolton’s handiwork.

Fisher’s argument was that Oesterlund had begun offshoring the companies to shield himself from consumer lawsuits, but then, as a divorce grew imminent, redeployed the same plan to shield assets from Pursglove. And that assertion was bolstered by a new discovery.

Studying bank documents Fisher had subpoenaed, Fisher’s paralegal, Lindsey Crews, noticed that Pursglove’s stamped signature appeared on paperwork in early 2013 that gave an Xacti executive named Skip Middleton, Oesterlund’s right-hand man, authority over at least six Xacti-related bank accounts with Wells Fargo. A few months later, Middleton used his newfound authority to remove Pursglove from the accounts. Not long after, around the time Oesterlund created the Cook Islands trust, someone using Pursglove’s signature stamp had caused RSOP, the family holding company, to guarantee a $17.5 million loan from a Florida lender called C1 bank, using the Déjà Vu as collateral. The loan papers attested that Middleton had witnessed Pursglove signing for the loan in Florida. But Pursglove wasn’t in Florida on the date indicated: Her passport stamps proved that she was actually in Toronto.

A clearer picture emerged as they studied documents subpoenaed from Daszkal Bolton. It turned out that in early 2013, after Pursglove asked Xacti’s executives to inform her of any large cash transfers or major business decisions, Oesterlund ordered Middleton to cut her off. Over email, he told Middleton to ban her from their Boca Raton offices and to remove Pursglove as a signatory to the company bank accounts. Middleton forwarded the email to a Daszkal Bolton accountant. “Umm, Houston, we have a problem,” Middleton wrote, referring to Oesterlund’s demands. The bank forms adding Middleton to the accounts — supposedly with Pursglove’s permission — were filed two days later.

A lawyer for Middleton did not reply to a request for comment. (When Fisher deposed him this past April, Middleton invoked his Fifth Amendment rights almost 300 times, including to the question of whether he had forged Pursglove’s signature.) A spokesman for Daszkal Bolton told me that the firm would not comment on litigation or client matters. But documents obtained by Fisher suggest that Oesterlund’s lawyers and accountants had indeed spent 2013 trying to make him untouchable, trading complex organizational charts, debating what companies to create in which countries, even what value to assign them.

Early in the fall of 2014, Fisher printed out a copy of the Xacti organizational chart and taped it behind his desk. He ordered everyone in the office to keep a copy as well. Every time they found a new Oesterlund company, they would add it the chart, which came to resemble a convoluted treasure map. In the Caribbean, there were shell companies with names like Paradise Liquidity I and Integrity Investment Holdings, formed by a Nevis holding company and then immediately transferred to Oesterlund’s Cook Islands trust. There was a second Cook Islands trust, also created in June 2013, right as the Florida attorney general began nosing around Oesterlund’s businesses again. There was $35 million or more in cash, in bank accounts in, among other places, Monaco, Luxembourg, Canada and the Bahamas.

Fisher’s legal assault now presented Oesterlund’s helpers with a painful choice: Protect one client, or protect the system.

Yet on paper, it was hard to find anything that Oesterlund actually owned himself. Shortly after Judge Gillen froze his assets, Oesterlund removed himself as a “beneficiary” of the two trusts, even though they now appeared to contain much of the family’s businesses and property. The Toronto penthouse was now owned by a Delaware corporation, which was owned by a Nevis corporation deposited in one of the Cook trusts. At some point, Omega had also been transferred into one of the trusts. The Déjà Vu, meanwhile, was now owned by a Caymans corporation whose “membership interest” — its ownership — had been shifted into one of the trusts. In exchange, the trust paid Oesterlund the sum of $100.

Unknown to his wife, Oesterlund had even purchased an apartment complex in Georgia, using $23 million in loans backed by the Housing and Urban Development Department. The application, which Potter obtained with an open-records request, was personally signed by Oesterlund, who listed an address in Boca Raton where he hadn’t actually lived in at least four years. But after the sale closed in 2013, other documents indicated, control of the apartment complex was shifted to a Bahamian company, and finally into the trust. The United States government appeared to be guaranteeing a $23 million loan to a Cook Islands trust in the South Pacific.

Oesterlund’s legal strategy was also becoming clear: Don’t explain anything. The trusts had hired a small Miami law firm called Kaplan Zeena, whose lawyers excelled at navigating the complexity and opacity of the offshore legal world. They cited obscure international treaties and arcane points of Caribbean law, Potter told me. They filed endless procedural and jurisdictional objections, burying Potter and Fisher in paperwork. Pursglove was now receiving alimony and child support, but much of it was taken up paying off a jumbo mortgage and back taxes; Fisher would get paid for his firm’s work only if she won. (Kaplan Zeena, too, did not respond to emails seeking comment.)

Potter, who had to write most of the replying briefs, believed that Oesterlund’s trusts were filing motions or objections it seemed certain to lose, just to exhaust and bankrupt Pursglove. In one lawsuit, the trusts fought against releasing a single piece of paper. The goal wasn’t merely to win, Potter felt, but to prevent the case from progressing far enough for its actual merits to be heard. “This isn’t some weird aspect of the process,” he says. “This is the game itself.” Nor could Fisher, despite invoking the authority of the Florida attorney general against Oesterlund, count on help from the actual Florida attorney general. The office had sent a lawyer to monitor at least one hearing in Pursglove’s lawsuit, but had taken no official position on her claims. Fisher was on his own.

But in the late fall of 2014, Oesterlund ran short of a commodity that had once seemed in bountiful supply: time. For many months, his lawyers had successfully delayed Fisher’s demands to depose him in person, insisting on a variety of jurisdictional, geographic and practical complications. In the process, however, Oesterlund had exhausted the patience of a series of Florida judges. Now, under threat of being held in contempt (and, potentially, the court’s issuing a warrant for his arrest), Oesterlund agreed to show up in a Toronto law office.

A video of the day shows that he arrived a few minutes late. “You’re shorter than I thought you were,” Oesterlund told Fisher. But for the rest of the deposition, Oesterlund was studiously restrained. He answered most questions in a monotone, rarely meeting Fisher’s eye. Fisher tried repeatedly to get Oesterlund to list his assets. “I owned lots of assets, different assets, various assets,” Oesterlund said vaguely. He had “things that most people would have, like a watch.” Was he really worth $401,769,834, as his accountants once thought? Oesterlund waved the question away. “I don’t know where these numbers are taken from,” he said, staring fixedly at the table. How did the penthouse end up in a Cook Islands trust? It was “a transaction between me and my attorney.” Which attorney? “I can’t remember,” Oesterlund retorted. “I have too many.”

But bit by bit, Fisher began to connect Oesterlund back to his own wealth. Oesterlund admitted that he had signed a rental agreement to live in the Toronto penthouse now owned by the trust. In that case, Fisher asked, was Oesterlund paying rent? Oesterlund looked up at the ceiling. “It’s being accrued,” he replied; no money was actually changing hands. Under orders from Rosen, one of his lawyers, Oesterlund refused to say who was paying the utilities and maintenance at the penthouse. But he admitted that the trust was paying to fuel, maintain and crew the Déjà Vu — a boat that he was the only person permitted to use, according to a copy of the boat’s insurance contract.

Documents accompanying the deposition provided further evidence that there was little distance between Oesterlund and the theoretically independent trusts holding his former property. The trusts were paying to furnish Oesterlund with a private helicopter and even fund his trips to St. Maarten.

In court papers filed that spring and summer, Fisher and Pursglove’s Toronto divorce lawyer, Harold Niman, sharpened their attacks. Oesterlund was “a highly successful internet swindler,” engaged in “internet scams, forgeries, tax fraud, bank fraud, HUD fraud, immigration fraud, fraudulent overseas transfers and other misconduct,” Fisher told a Florida judge. They also moved to freeze even more of Oesterlund’s income, and not just to make him suffer personally. Fisher and Potter estimated that Oesterlund was burning through about a million dollars a month, much of it going to pay the lawyers and accountants keeping his maze of trusts and shell companies in working order.

In March, Fisher went after Wells Fargo, Oesterlund’s main link between the name-brand financial-services world and the gray market of offshore shell companies and trusts. The Wells Fargo accounts, they believed, were still accumulating revenue from some of the old Xacti businesses — the ones selling travel deals or DVDs or antivirus toolbars — some of which had been reconstituted under new, offshore corporations. Fisher, citing Pursglove’s possibly forged signature removing her from the accounts, threatened to sue Wells Fargo, asserting that the bank had allowed Oesterlund to defraud his wife of millions of dollars. Because of the competing claims to the accounts, Wells Fargo quickly froze them until the dispute could be settled. Now neither Oesterlund nor the trusts could access the money.

An even bigger threat to Oesterlund began taking shape in June 2015, when a Florida judge ruled that Pursglove was entitled to view thousands of pages of emails and documents exchanged by Oesterlund and other executives at Xacti with their lawyers. Oesterlund’s attorneys had tried to keep the documents out of court, arguing they were protected by attorney-client privilege. Fisher was certain the privileged documents would contain what he called a “smoking gun.” He wouldn’t just see where the money was hidden, Fisher believed. He would see Oesterlund plotting how to hide the money. He would get not only direct evidence of fraud against Pursglove and others, but also emails and memos that might implicate many of the lawyers and accountants who had helped him. The whole thing could be laid bare.

A few days later, Oesterlund’s lawyers asked for a meeting, hinting that if Fisher got the privileged documents, their client would go on the run. Whatever Oesterlund was hiding, it was so damaging that he was willing to live in virtual exile in order to keep it from his wife.

Credit Illustration by R. Kikuo Johnson

Fisher and Potter strolled down the block in West Palm Beach to the offices of Squire Patton Boggs — a well-regarded multinational firm that represents Oesterlund’s Florida companies — to hear them out. The suggestion made everyone wary. Pursglove could lose by winning: If her husband went into hiding, it would be hard to wring money out of him. But it would also be bad for Oesterlund’s lawyers, particularly for the Americans. For one thing, Potter would later realize, Oesterlund now had large unpaid legal bills. And beyond the financial risk was a reputational one. It was one thing to defend a businessman in a civil suit. It was another to defend a fugitive.

Documents turned over at the June meeting and subsequent ones that summer laid out Oesterlund’s position. Most of his net worth was tied up in the value of his companies, and they were worth less than his accountants once claimed. He didn’t actually have enough wealth to give his wife half of a $400 million estate — the sort of net worth he once declared in order to secure loans for a jet or Georgia real estate. But now the baroque complexity of Oesterlund’s finances had become a noose around his neck. To prove that Oesterlund’s fortune was much smaller, his lawyers had to reveal where and how he had hidden it. If they refused, and a judge decided to award Pursglove $200 million, Oesterlund wouldn’t have enough liquid wealth to pay up. He could be ruined.

Trapped, Oesterlund’s lawyers were now doing Fisher’s work for him, providing documents that suggested further violations of the Judge Gillen’s original asset injunction, Potter told me. One trust had recently sent Oesterlund’s lawyers more than $1 million to cover legal fees. In Potter’s opinion, Oesterlund had no choice. He “had to decide whether to pay the lawyers, and expose that he could get cash from the trust whenever he wanted,” Potter says, “or not pay them, and not be able to fight the suit.”

Another bank statement they handed over showed that on a single day in 2014, Oesterlund transferred $48 million into one of the Cook trusts. It was the same day, Fisher quickly realized, that Pursglove discovered Oesterlund with his new girlfriend. Fisher believed this would be strong evidence in court that the trust had been set up in anticipation of owing his wife money, which even in most offshore jurisdictions is against the law.

Hundreds of thousands of dollars had been drawn out of one trust each month to operate the Déjà Vu. Fisher’s paralegal hunted for the boat in Oesterlund’s usual haunts. Using public webcams at ports around the French Rivera, she discovered the Déjà Vu anchored in the middle of the harbor in Saint-Tropez. Potter took a working vacation to France and, after a few days of carefully planned sightseeing, found the boat anchored in Nice. Halfway through a meal at the Grand-Hotel du Cap-Ferrat, he also found Oesterlund himself, who strode out onto the dining patio with the interior decorator. Potter’s own girlfriend snapped a picture on her cellphone. They left quickly, before Oesterlund noticed them.

In Florida, Oesterlund’s lawyers were again running out of time. Oesterlund was now subject to an increasingly stern series of court orders that he turn over the privileged documents, regardless of any potential settlement.

This didn’t just threaten Oesterlund’s fortune. It also had the potential to carve open a portal into the world of offshore finance, a place that the global elite has spent hundreds of millions of dollars to build and defend. In the offshore archipelago, their interests are hidden behind shell companies and trusts, their anonymity guaranteed under the law, from Delaware to the Bahamas to the South Pacific. James S. Henry, a former chief economist at McKinsey, calls the offshore financial world the “economic equivalent of an astrophysical black hole,” holding at least $21 trillion of the world’s financial wealth, more than the gross domestic product of the United States.

This darkness shields the tax-averse businessman and the criminal alike. Dictators use the offshore system to loot their own countries. Drug lords use it to launder money. As Gabriel Zucman, a University of California economist and an offshore expert, puts it: “They use the same banks, they use the same incorporation agents to create shell companies, they send money in the same ways.”

But when the wall of secrecy is breached, the distinction between upright global citizen and criminal can quickly grow indistinct. In April, media outlets belonging to the International Consortium of Investigative Journalists published a trove of confidential records leaked from the Panamanian law firm Mossack Fonseca, exposing the offshore financial holdings of various kleptocrats and forcing the resignation of the prime minister of Iceland. Leak the client files of a single middling law firm in Panama City, and you can take down governments half a world away.

If Fisher could prove that one Cook trust was a sham, then the settlors and administrators of other Cook trusts could have a harder time defending them in reputable courts. For attorneys and accountants working in the offshore industry, having private correspondence with a client entered into a public court record would be a disaster. Anybody could see what they were doing and how they did it. Fisher’s legal assault now presented Oesterlund’s helpers with a painful choice: Protect one client, or protect the system.

Soon, the tangle of defenders who had once guarded Oesterlund’s wealth started to turn against him. One rainy Friday in July 2015, after losing an appeal on the treasure trove of privileged documents, Oesterlund’s entire team of lawyers at Squire Patton Boggs abruptly quit. Oesterlund, Potter learned, had ordered them to ignore the court’s order to turn over the documents, a serious violation for which the lawyers, all American citizens, could have been disbarred.

They rejoined the case within days, after Oesterlund agreed to let them release a portion of the files. But it was a sign that Oesterlund had begun pushing his camp into dangerous territory, both professionally and legally. The wall of secrecy around Oesterlund’s offshore holdings began to collapse. The first batch of documents, five or six notebooks’ worth of emails arrived last fall. More would soon follow.

When I spoke with Fisher by phone in February, he sounded confident. Oesterlund appeared to be running out of cash, Fisher told me; he was missing payments on the loan from C1 Bank. In August, after further delays in producing the documents, Judge Gillen held Oesterlund and his companies in contempt of court, dangling the prospect of criminal penalties. Soon after, Oesterlund’s personal lawyer in the case quit, citing “irreconcilable differences” with his client. Court filings this fall suggested that the civil litigation was drawing to a close, though both Fisher and Oesterlund’s remaining lawyers said they were barred from discussing any final settlement.

More even than the laws of the world’s tax havens, the offshore financial system is kept afloat by the legions of professionals — accountants, lawyers, incorporation agents — who are paid well to service it. But the people who work to dismantle that system also have to be paid. If the case Fisher had constructed against Oesterlund was correct, I once proposed to him, then at least some of the money coming to him and Pursglove would seem to be tainted. Fisher disagreed, and unspooled an intricate accounting of his own. When he cracked open the Cook trusts, Fisher argued, the money would come back home. Whatever liabilities Oesterlund had to consumers would be payable by what remained of the businesses. Pursglove and her payout would live in Boca Raton, within easy reach of United States law. “I would always view the dollars that I get to be legitimate dollars,” Fisher said.

But this would be a justice of wealth battling wealth, hammering through the veneer of trusts and shell companies to serve private ends. Fisher’s own role as public crusader would end, circumscribed by Pursglove’s interests. He and Potter had sent packages of evidence to the Palm Beach sheriff’s department, the inspector general of HUD, and the United States attorney’s office. Those authorities might take a hard look at Oesterlund’s business dealings and the well-paid professionals who made them all possible. Or they might lay the packages aside, alongside other complex cases that take extraordinary amounts of time and money to pursue. “In the end, I’m not a private attorney general,” Fisher mused. “I’m a private attorney.”