Famous for its aggressive advertising and extravagant parties, the firm came to employ more than 2,000 people, occupying nine floors in a San José office tower. Bettors, mostly American, wagered on everything from pro basketball to university cricket, as well as offbeat "proposition bets" including, "What date will the war in Iraq begin?" and, "Who will first be arrested for wife-beating: Bobby Brown, Jean-Claude Van Damme or Dennis Rodman?"
"I'm a believer in Rodman all the way, so the odds on him were short," Kaplan told the Miami Herald during a rare interview in 2000. "Bobby Brown, you think maybe Whitney [Houston] will keep him in check a little bit, so we put him down at the bottom."
In 2004 Kaplan's company went public on the London Stock Exchange, raising $44 million in capital and netting proceeds and stock worth hundreds of millions of dollars not bad for the eldest son of a working-class New York garment salesman. All the while, Kaplan was betting that the U.S. Department of Justice would leave offshore Internet bookmakers alone, saying that they'd long operated under murky legal conditions.
For years U.S. lawmakers have tried to ban the $12 billion online gambling industry, which can include sports, poker and casino-style betting, and is legal in more than 80 countries. The Justice Department considers the business to be in violation of the 1961 Wire Act, which prohibits the use of a wire communication facility" to transmit bets across state or foreign borders.
Some attorneys argue, however, that the law is antiquated and applies neither to Internet gambling nor its offshore purveyors; Gary Kaplan rolled those dice for years. But it all came up snake eyes on July 17, 2006, when the U.S. Attorney's office in the Eastern District of Missouri unsealed a 22-count indictment charging him with racketeering, wire fraud, tax evasion and other crimes. Federal authorities proceeded to arrest eight of his alleged co-conspirators, among them, BETonSPORTS' Scottish CEO and two of Kaplan's siblings. The government also set about seizing more than $4.5 billion in assets including cash, Hummers and luxury RVs associated with Kaplan's gambling empire.
The economic fallout was disastrous: Just one day after the indictment, investors in other public gaming companies watched their share value plummet. BOS shut down its operations, fired its CEO and left customers in the lurch for millions of dollars. Privately owned gambling firms hastily fled one offshore location for another.
Gary Kaplan, facing 83 years in a federal prison, proceeded to travel the world in pursuit of new business ventures, even sealing a deal for a new online wagering game he called Mr. BidLow. According to court papers, he moved by air and by sea between Israel, Venezuela, Argentina, Colombia, Peru and Uruguay. Authorities do not believe he set foot in Costa Rica, where his wife, Holly Kaplan, and two young children resided under the watch of the family's personal bodyguards.
On March 27, nine months after the indictment was issued, the stocky, chestnut-haired fugitive entered the Dominican Republic and, according to court documents, checked into a hotel under the name Allan Andre Viaux. People close to Kaplan say he intended to join his family at a vacation home and enjoy one last Easter holiday together before turning himself in. But Interpol, watching his every move, arrested him the next day.
Court filings show Kaplan was carrying $11,000 in various currencies, two fake Peruvian passports, an Israeli passport issued to Meir (Gary Stephen) Kaplan and a Dominican passport in the name of Gary Stephen Kaplan Pearlman. Kaplan's attorneys explained that Kaplan had long thought of relocating to Israel by virtue of his Jewish birthright, but offered no explanation for the phony Peruvian documents.
Officials also confiscated steroids purportedly to assist Kaplan in bodybuilding and a spiral-bound notebook with a handwritten to-do list, entitled "Nicaragua: Requests." Kaplan's notes read:
(3) possible diplomatic (no questions)
(4) citizenship & Passports for my family
(5) asylum (written Protection from USA legal documentation all 22 counts charges).
(6) landing right for helicopter. Specify location other than Major airport. (I'll pay for govt. agent to supervise) (custom agent stamp in stamp out...)
The last item to catch authorities' attention upon Kaplan's arrest was a handcuff key found in his backpack. The government contended he was previously detained in Venezuela and bribed police, receiving the key as a parting gift. Prosecutors considered it a sign that Kaplan would stop at nothing to elude law enforcement. Kaplan's attorneys, on the other hand, claimed he was kidnapped after vacationing in Venezuela with his family and that the key was a memento from the "intermediary" who secured his freedom.
Interpol swiftly transferred Kaplan from the Dominican Republic into U.S. custody at a Puerto Rico jail, where he remained for more than a month before arriving in St. Louis this past May. The government asked U.S. Magistrate Judge Mary Ann Medler to keep him locked up until trial.
On May 25, during Kaplan's first detention hearing, his father-in-law, a rubber-products magnate, took the stand and offered to put up his two vacation homes in Colorado and Florida, a combined value of $7 million, as collateral for Kaplan's bond. "I have total faith and confidence in my son-in-law," said Warren Hoeffner, of Tyler, Texas. "I don't think he would do anything to hurt his family, his children or me."
But Assistant U.S. Attorney Mike Fagan, a career federal prosecutor who pursued BETonSPORTS for more than four years, tried to discredit Hoeffner by claiming he loaned Kaplan seed money for BOS' early advertising campaigns. A devout Methodist who doesn't believe in gambling, Hoeffner clarified that he refused to help Kaplan but that his wife (who enjoys gambling) had made several loans to their son-in-law.
In a subsequent court order on June 13, Judge Medler made note of Kaplan's criminal past, including convictions for cocaine possession, credit card forgery and promoting gambling in the second degree, all which Kaplan accumulated before starting up BOS. Judge Medler also noted that Kaplan owned six guns, six cars and two expensive homes in Costa Rica, and that Kaplan and his wife had numerous bank accounts, with at least $100 million at their disposal.
"On his flight from the Dominican Republic to Puerto Rico after his arrest," wrote Judge Medler, "defendant made an unsolicited statement to the FBI agents to the effect that the longer he stayed on the run from American law enforcement authorities the more he thought he could outlast the Indictment." Medler ruled to keep Kaplan behind bars at the St. Louis County Justice Center.
Kaplan's team of ten attorneys pleaded for a second hearing. His legal brain trust included famed Harvard Law professor Alan Dershowitz and two noted Texans: Chris Flood and Dick DeGuerin. DeGuerin's best known for defending cult leader David Koresh and the disgraced former congressman Tom DeLay. U.S. District Judge Carol Jackson granted the request.
And so on September 5 Kaplan was back in court asking Jackson to place him on house arrest at his sprawling Portland Place mansion in the Central West End, which Holly Kaplan purchased for $1.5 million this summer. The brandy-haired Holly, an aspiring model when she met her husband in New York City sixteen years ago, watched the proceedings anxiously, clutching a smooth "good luck" stone, a present from her eleven-year-old son.
Judge Jackson had some unusual odds to consider: What would Gary Kaplan's prominent neighbors think of his wish to place armed security guards outside his home on the private street? And, if Kaplan himself was footing the bill, wouldn't it be easier for him to flee?
DeGuerin tried to assure Jackson that off-duty cops would turn Kaplan's home into "a virtual jail," replete with motion detectors, infrared monitoring and 24-hour physical surveillance. Visitors would be searched, and the Kaplan family frequent world travelers would surrender their passports.
But Fagan, the prosecutor, picked apart that scheme, arguing that it would be impossible to keep Kaplan from walking, driving or even flying away. "He does own a helicopter, by the way," he pointed out.
Gary Kaplan was 34 years old, newly married with two kids and was somewhat aimless in 1993, when he moved his family from New York to South Florida. He had tried out his father's trade and even dabbled in fashion design, but with little success. Kaplan wasn't in Florida long, however, before he heard about sports bookies traveling to the Caribbean to take bets from U.S. customers.
Enticed, Kaplan journeyed to Aruba in 1995 to investigate the new industry and then launched his own sports book. Two years later, Kaplan moved his family and business to San José, Costa Rica. With minimal licensing requirements, a burgeoning bilingual middle class and a stable government, Costa Rica was fast becoming the locus of the offshore betting industry, the so-called "Wild West." Kaplan made his memorable entrance by cruising San José's streets on a motorcycle, an American flag painted on its tank.
Kaplan soon met Norm "Stormin' Norman" Steinberg, operator of the Millennium Sportsbook. The 58-year-old Philadelphian had landed in Costa Rica in 1997, reportedly trying to evade an imminent federal charge of intent to distribute more than 500,000 prescription narcotic pills from his Philly pharmacy. According to former colleagues, the acquaintance was the beginning of a fruitful partnership, especially for Kaplan.
Affectionately described by friends as "a degenerate gambler," Steinberg is well-known for his Carlton Menthol 100s addiction and a missing middle finger, which, as the story goes, he "paid" to settle a gambling debt. In Costa Rica, Steinberg apparently began betting heavily with Kaplan's BETonSPORTS and losing. To settle his arrears, Steinberg is said to have shared Millennium's lucrative client list with Kaplan.
Among the some 200 bookmakers in Costa Rica in 1998, Kaplan swiftly distanced himself from the herd. For one thing he was a workaholic, at the office seven days a week. He rarely joined the hard-partying bookies at nearby bars. Kaplan further distinguished himself by launching a marketing assault unheard of in the industry, which typically won customers through word-of-mouth. Kaplan bought full-page ads in mainstream venues, including Maxim magazine and Pro Football Weekly. He aired regular radio spots on The Jim Rome Show. Kaplan also leased billboards around the country to display BOS' vanity phone number and Web site, and flooded potential customers' mailboxes with promotions.
"You have these bookmakers that were used to having customers on the streets in New York or LA, you throw them in a foreign country with an Internet site and they don't know what to do," says Ken Weitzner, owner of the Eye On Gambling Web site. "Gary understood this was big business and he knew you had to market it all over the place."
Kaplan also tried to corner the market by opening Web sites under hundreds of different names. "It was smart," observes Tom Jensen, publisher of www.Point-Spreads.com, a gambling news portal. "Gamblers are by nature superstitious. They lose at one book and they like to move along to another one for awhile."
It was reputed that Kaplan also maintained a financial arrangement with a Web site calling itself the Off Shore Gaming Association. The site once claimed to be a "watchdog" but steered bettors toward certain books. BOS and its affiliates were regular "favorites."
"It was a sham, funded by BOS," explains a former employee who says he saw records of checks written to the OSGA Web master. "We'd tell bettors, 'We're approved by the OSGA,' which is like saying, 'We're approved by ourselves.'"
Gary Kaplan was amazed at how quickly business grew. His younger sister, Lori Kaplan Multz, and brother, Neil Kaplan, soon left their spouses and children in the U.S. to get in on the action. The family kept a low profile, steering clear of well-recognized trade conferences and adhering to an age-old gambling practice of using aliases.
Matt Lindvall, a Southern Methodist University graduate who worked for BOS for two years, says the Kaplans were wary of law enforcement. "In my interview, Scott [Neil Kaplan] asked me what the hell I was doing there and why did I want to work for $300 dollars a week. He was a little worried at first because I was well educated. He asked me if I was F.B.I., and I said, 'No, no, I'm just a guy who wants to smoke pot and surf.'"
Lindvall, the son of a preacher, says the company set him up with an alter-identity Max Anderson complete with a bank account and an ID card. He worked in accounting as well as sales, where he sat in a room with hundreds of bilingual operators answering calls from bettors. The staff instructed gamblers to wire their money to a fictitious name in such countries as Ecuador, Antigua and Belize.
"We had runners in different countries that would go to the Western Union office and pick up all the funds and transfer them to us at the end of every day," explains Lindvall. "We'd make up horribly funny names, like Dick Trickle and Big Tits McGee, that the customers would have to write on their wire forms."
The industry calls this betting model "post-up." A gambler sends money offshore so the bookmaker's representatives can then "place" the gambler's requested bets using offshore banks. According to Lindvall, winnings were wired back to the gambler in increments of less than $10,000 and sometimes even distributed in person. If a bettor was worried about getting his money back, adds Lindvall, "we would say things like, 'ESPN wouldn't let us in to advertise if we weren't legitimate.'"
Football and basketball seasons were the most hectic time, forcing the company to take on extra staff. Promotional materials touted the firm's more than 2,000 telephone lines and computer servers that could process 5,600 simultaneous Web transactions.
"I was in the office for the first day of NFL football, both in 2000 and 2001, and it was fascinating," reports Chris Costigan, publisher of an online tabloid, Gambling 911. "In 2000 they had so many people calling in during those hours leading up to the first kickoff that their phones all crashed. Everything went dead. The following year Gary invested in his own technology, like satellites and in-house phone lines." Says Lindvall: "They would take in $11 million, just on NFL games, in a single Sunday."
The company was known as one of San José's best employers; lawyers and doctors made more working in the BOS sales department than in their given professions. The firm also offered extra perks to certain employees. "They flew me back to the U.S. for vacations and weddings and put me up in a free apartment," recalls Lindvall. "They paid for a maid who rolled my joints, did the laundry and made me rice and beans."
A former stockbroker, Lindvall says he was not the average American on the BOS payroll: "It was a bunch of riffraff. There were several of us guys who went to Costa Rica to party, which is bad enough, but the older guys who supervised different departments they were all running away from something: the ex-wife, the current wife, the IRS or felony charges in Nevada. You had the dregs of society running this thing."
Gary Kaplan kept to himself within the chaotic office, mostly issuing orders through his brother. The company was obsessed with penny-pinching; employees had to bring their own pens to work and Neil Kaplan had to approve every payout. "They were more fearful of people illegitimately winning than the feds coming after them," says Lindvall. "When somebody legitimately won big, it made them angry."
BETonSPORTS was open for business 24 hours a day, 365 days a year. Says Lindvall: "Scott (Neil Kaplan) and G. (Gary Kaplan) worked hours and hours and hours, and the only thing they ever talked about was money and gambling. Some people talk about the weather, or how the Jets are doing, or how's your wife? or did you get laid last night. None of that ever came up. It was just about how much money can we make and how can we make more."
According to the indictment, BOS hauled in gross wagers of $1.09 billion, $1.23 billion and $1.24 billion in 2001, 2002 and 2003, respectively. Recreational bettors accounted for most of the proceeds. "They only liked having the guys that didn't know what the hell they were doing, because it was more profitable for them," observes Tom Jensen of Point-Spreads. "Gary Kaplan had the reputation of pardon my French telling the professional bettors to fuck off. He didn't make a lot of friends."
Weitzner, operator of the Eye on Gambling Web site, agrees. Citing an alleged incident in the late 1990s in which a well-known West Coast gambler had a "beard," or stand-in, wagering bets for him at BOS. According to Weitzner and others, the beard first lost thousands of dollars with the book, but then rebounded to win upward of $200,000. "Gary promised to make good on the bets, and he never did," says Weitzner. "I went down there a couple times to try to negotiate a deal. Gary gave a choice as to several payment methods or options, but he never honored them."
As Weitzner tells it, a lawyer also tried to collect from Kaplan on behalf of the West Coast bettor. "The attorney is inside Gary's office asking for a settlement and Gary has a gun that he spins around and says, basically, 'I can kill you now, or I can kill you later.'" Weitzner adds: "This story was put up on every gambling message board."
"'Crazy G.' was Gary's nickname," remembers Roberto Castiglioni, a one-time operator and the publisher of The Online Wire, a gambling Web site. "Everybody knew him and his employees for these kinds of behaviors. They were the bad apples, the thugs, the ones that gave the biggest contribution to destroying the image of an industry that was seeking regulation."
Eduardo Agami disagrees. "Gary is a stand-up guy," says Agami, president of a gambling trade association in Costa Rica. "We'd speak with politicians, meet with the presidents of the country and high-ranking officials about more regulation and better licensing, and he deferred to my position, never felt the need to undermine or compete with me."
Kaplan was technically a competitor, since Agami also ran an Internet gambling operation. But Agami considered Kaplan a friend. In fact, adds Agami, "If I was going to the beach, he would lend me his helicopter."
Kaplan in 2000 placed an ad in the Daily Racing Form looking for a CEO. The ideal candidate would have no interest in the minutiae of BOS' daily operations. Instead, the CEO would be an ambassador, so to speak, a professional public face for the business.
"Gary had come up with a plan to take the company public," recalls Weitzner. "He bragged about it to me. He said he was going to make his millions through stock. I laughed at him. I said, 'How are you going to go public? You're a bookmaker with a bad record.'"
Kaplan's answer was David Carruthers, a Scotsman who, at age nineteen, had become the youngest manager at the elder statesman of British betting shops, Ladbrokes. With an MBA from a British university, a grasp of international politics and a wide-reaching professional network, the 50-year-old Carruthers, according to insiders, became the crux of Kaplan's so-called "escape strategy."
"David was a breath of fresh air for the industry well-respected, intelligent and well-rounded," remembers Kevin Smith, a former trade reporter who later became the spokesman for BOS. "When I covered the business I was used to dealing with fuckwads who'd say, 'I'm going to do so much for this industry,' and then never did a thing. With David, for once, I wasn't dealing with a used-car salesman."
Carruthers and Kaplan first attempted to float BOS on the London Stock Exchange in late 2001. When that failed, Kaplan reportedly retreated from the view of potential investors, apparently to buff up the corporate image of the company so convincingly portrayed by Carruthers.
Many believe it was Kaplan, however, who in 2002 quietly orchestrated BOS' most ballyhooed public relations campaign to date. The company plastered its name across a pair of luxury RVs and a PT Cruiser, recruited a squad of scantily clad "BOS Girls" and on game days parked the caravans outside NFL stadiums including the Edward Jones Dome.
The firm kicked off the season with an extravagant bash atop its San José headquarters in its brand-new "VIP Club" featuring twelve adjoining suites, a cigar shop, blackjack tables and a pool bearing the BOS logo on its bottom. Soap suds wafted about the room while Carmen Electra and the Pussycat Dolls headlined the event. Models flown in from the United States entertained high-rolling customers in themed rooms like "Catholic School Girls" and "Dominatrix." Celebrities and assorted tabloid TV and gossip columnists were in attendance.
All of this, the industry knew, was being carefully monitored by law enforcement. Only a month before the bash, the U.S. Attorney for the Eastern District of Missouri subpoenaed PayPal about its Internet gambling transactions. At the same time lawmakers in Congress were reviewing bills aimed at stymieing the industry. The scrutiny did nothing but embolden Carruthers. The following year he hit the road to educate U.S. media, lawmakers and lobbyists on industry practices and quickly distinguished himself as the trade's poster boy for regulation.
"You have to wonder when the U.S. will wake up and get a clue on what the rest of the world is doing," Carruthers once said. "You have operators begging to be taxed in the U.S. and all the politicians want to do is try to pass legislation that is aimed at prohibition."
In fall 2003 the industry suffered an economic blow when such media outlets as the Howard Stern Radio Show and The Sporting News yanked ads because of the St. Louis-based investigation. Carruthers responded with a petition drive calling for an end to the inquiry. In BOS' typically brazen fashion, he rolled out the campaign on the stoop of Stern's parent company's headquarters in New York. "The only thing that would have been better was if they had brought the microphones down to the street and interviewed us," Carruthers told the St. Charles-based Interactive Gaming News.
Carruthers' then-attorneys advised that because he was a UK citizen the U.S. government had no standing to arrest him. But in fact, he would be the first taken into custody nearly three years later.
In 2004 prosecutors offered a plea bargain to a Miami marketing vendor who'd coordinated promotions for BOS. The firm's attorney was unconvinced that laws were broken and refused the deal. The same year, Norm Steinberg paid a visit to prosecutors in St. Louis. The exact details of their conversation are unknown. According to court filings, however, Steinberg returned to Costa Rica with a message for Gary Kaplan: "The prosecutors wanted Gary Kaplan above all else."
BETonSPORTS planned to open its 2006 football season with a $30 million ad campaign featuring nuns: inflatable women of the cloth flying over football crowds and alongside BOS billboards with the tag line: "Last night Sister Marietta won a Hail Mary." The promotions would have set a decidedly new image for the company.
David Carruthers had overhauled the management of the firm in the two years since its public float, a fact he touted in annual reports. Neil Kaplan by now was long gone. Lori Kaplan, reportedly to her dismay, was let go in 2005. Norm Steinberg no longer had an office in the building. BOS, to be sure, was no longer a family business.
Carruthers professionalized the operation by bringing in a cadre of British executives with decades of experience in the business. They were beginning to upgrade technology and weed out drug-addled employees. Kaplan, for his part, had become depressed after selling most of his shares and gone on a two-week cocaine binge, according to court papers. But by 2006 he was consulting for the company again. Former employees say he was helping BOS strike partnerships in South America while Carruthers worked on business development across Asia.
In the company's annual report dated May 31, 2006, Carruthers stated: "BOS will remain at the forefront of any debate, winning friends and influence." Unofficially, the firm was predicting profits of $44 million for the coming year. The very next day on June 1, a grand jury in St. Louis handed down its sealed indictment. Six weeks later authorities arrested Carruthers at the Dallas airport as he and his wife made their way to Costa Rica from London. According to a friend, Carruthers had no inkling of the magnitude of the charges he was facing. He thought the company would bail him out the next day and business would go on as usual.
On the contrary. The BOS board of directors fired Carruthers a week later, most likely in hopes of avoiding prosecution. For the last year the Scot has been under house arrest at a rented apartment in Clayton on the Park, learning Mandarin Chinese, watching Boston Legal and rooting for the St. Louis Cardinals. BOS went belly-up last fall.
"There was talk right after the arrest that Gary would never have shut down the company," says Tom Jensen. "He would have made them drag him out of there. The problem was they had become so transparent by becoming a public company. If they were still private, Gary would have probably said to the feds, 'Come on down here and pound sand.'"
To this day speculation rages in the industry as to why BOS became a Justice Department target. Some people believe it was because there was illegal "credit" betting allegedly occurring under Kaplan's watch. The old-school, corner-bookie business model basically allows a gambler to make multiple wagers without depositing money offshore. On the weekly "settlement day," an "agent" and the bettor meet to collect or pay out.
Other insiders blame Kaplan's and Carruthers' aggressive self-promotion. Many believe the public disclosure associated with the company's IPO precipitated its demise. "There are people that have filled the void left by BETonSPORTS," observes Chris Flood, Kaplan's lead attorney.
The gambling community also remains mystified about the decision to prosecute the case in St. Louis. Undercover F.B.I. agents placed wagers with BOS from computers and phones here, but that is the company's only ostensible link to the city. Government sources, who asked not to be identified, said the decision was merely a question of resources and experience.
Lawrence Walters, a Florida-based attorney who specializes in Internet law and once advised BOS, believes the U.S. Attorney's case has problems. The Wire Act, he says, "Was intended to address your run-of-the-mill bookies who were accepting bets with paper notes and taking them to organized crime families. That's not what is going on with Internet gambling. These are multimillion-dollar companies listed on foreign stock exchanges, operating in countries with licenses issued by their own governments." The U.S. Attorney's Office declined to comment for this article.
According to an affidavit, the prosecutors' investigation continues. They recently indicted Kaplan's longtime bookkeeper, 62-year-old Penny Tucker of Miami, who allegedly controlled at least one of Kaplan's bank accounts one that helped him remain on the lam. A confidential source for the government saw Tucker being escorted to the San José airport in Costa Rica by Kaplan's bodyguards last December. Gary Kaplan himself was just leaving Israel at that time, where he had apparently been since the first round of arrests in July 2006. His friend Eduardo Agami ran into Holly Kaplan not long afterward.
"They were speaking on the phone and I said, 'Let me say hello,'" recounts Agami. "I said, 'Hi, how are you doing, I hope everything's all right and I hope to see you soon.'"
To which Gary Kaplan replied, "Me too."
Holly Kaplan was still grasping her "good luck" stone after her husband's second detention hearing ended September 5. "I'm doing OK," she says. "It's the hardest for my kids. They keep asking, 'Why our daddy? Why our daddy?' In Costa Rica all their friends' dads were in this business."
During the hearing Judge Jackson repeatedly expressed her "fundamental problem" with a defendant paying for his own security. On September 28, Jackson denied Gary Kaplan's plea to be placed on house arrest. The court is currently considering the defendants' motions to throw out the charges, on the basis of World Trade Organization rulings that the United States' attempts to ban Internet gambling violate international treaties. No trial date has been set.
Two weeks after the hearing Holly Kaplan left the country for some spiritual rejuvenation her mother, Sandra Hoeffer, says. "I'm disappointed that for all the good they did for the people of Costa Rica the government did not stand behind him," says Hoeffner, referring to charitable projects with orphanages, health clinics and victims of domestic abuse, which her daughter funded.
As for Gary Kaplan, according to Hoeffner, he's holding up well, appreciative of little luxuries like a makeshift tuna casserole prepared from staples he buys at the prison commissary. No gourmet, Kaplan always did like to cook.
Asked about Kaplan's motivations, Hoeffner sums it up this way: "This was never about money for Gary. It was about entrepreneurship. Gary was always working, from morning until evening. He ate and slept business. His mind never stopped. Even now he's probably in there thinking, 'I've got an idea for a business.'"