Double Down

"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."

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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.