Double Down

"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."

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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.