All In

Chuck Humphrey has based his career on gambling. Now hes calling the bet on online fantasy-sports competitions.

Around the same time, he created a team of poker players for whom he paid tournament entry fees in exchange for half their winnings. Team Pegasus, which eventually grew to twelve players, was a new twist on an old trade. "The idea of backing ten or twelve people, doing it on a fairly large scale, is something that hadn't been done," Humphrey says. "And doing it with written contracts and accounting controls hadn't been done, either. Now other people do it."

After a few years of backing his players and following the poker circuit from his forty-foot RV, he realized he wasn't going to make any money on the Tournament of Champions unless he could attract sponsors. For the 2001-2002 tourney, he hired Steve Lipscomb to film the event and gave him the television rights. "Steve did a horribly bad job for me. I had a tremendous falling-out with him, and I wound up closing down the TOC," Humphrey says.

Meanwhile, Lipscomb went on that same year to found the World Poker Tour, which debuted on the Travel Channel in March 2003. He took Mike Sexton with him as host. "That was really the single thing that caused poker to boom -- the original season of the World Poker Tour," Humphrey says. "I've never made up with Lipscomb, although out of a sense of honesty, every once in a while I've written something that will support what he does. But I don't like him very much."

Mark Andresen

Humphrey was left to look for a new venture. He was already fielding frequent legal questions about gambling on a poker newsgroup he frequented, so he decided to make a business of it. He wasn't licensed to practice law in California -- and at age sixty, he wasn't anxious to sit for the bar again -- so he returned to Colorado to research and compile the gambling laws of all fifty states. It was during that process that he came across the gambling-loss recovery statutes and started thinking about using them for a fantasy-sports suit.

Humphrey was sure the contests were based more on chance than skill, which could qualify them as gambling if he could prove the entry fee was in fact a wager. He concedes that drafting a fantasy sports team has an element of skill, but only to an extent. The actual outcome depends on what the actual players do on the field. "The proof in the pudding is something like the New York Yankees," he says. "Lord knows Steinbrenner pays an awful lot of money to buy the biggest-name baseball players, but they don't always play well. They don't always win the World Series."

In its motion to dismiss, CBS Sportsline and the Sporting News argue that the "entry fee" their websites charge is not a bet or wager, but a fee for services, like those real-time stats. Since the game is a test of team-management skills, players devote an extraordinary amount of time to monitoring such information -- three hours per week on average. The companies accuse their assailant of having "picked the wrong forum in which to pursue his legislative agenda."

Any legislative ambitions Humphrey admits to harboring remain in the realm of poker. At the suggestion of a friend in the online poker industry, he's been outlining a means to prove that online poker is a game of skill, and it starts with hiring the math department of a major university to do a statistical analysis of player outcomes over time. Such a study could prove useful as a lobbying tool or as evidence in court.

Humphrey may just take that bet.

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