Double Down

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.'"

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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.