Double Down

Gary Kaplan put all of his chips on BETonSPORTS and drew the worst hand of his life. Now hes making tuna casserole in a St. Louis jail.

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.'"

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