Daniel Kebort first thought of opening his own poker club on a cool night in the fall of 2010. He and a friend, Sam Von Kennel, were on an expedition. In Austin’s northern suburbs, they drove up to a brick house the color of sand and pulled onto its lawn, which had been transformed into a makeshift parking lot. On the Web site HomePokerGames.com, the house had been advertised as the location of Poker Social Club—an underground venue that claimed to operate legally, despite the fact that gambling businesses have been outlawed in Texas since before it became a state.

Earlier that fall, Kebort and Von Kennel had bonded over their shared love of Texas hold ’em. Hold ’em is a variant of poker that travelled from its namesake state, in the early nineteen-hundreds, to become, by many accounts, the most popular version played in casinos around the country; it differs from standard “stud” poker in that players share five cards (they hold just two in their hands) and have multiple opportunities to bet (and bluff) before a hand is finished. Every Thursday night, Kebort and Von Kennel played hold ’em with friends in a barn south of Austin. Such games, held in what the law sees as a “private place,” are sheltered from the state’s anti-gambling rules by what’s known as the social-gambling defense. Committed poker players who yearned for bigger, more glamorous games with higher stakes had two choices: they could drive to another state, where gambling was legal, such as Louisiana or Oklahoma, or they could use sites like HomePokerGames.com to explore the state’s underground scene.

At Poker Social Club, the two friends got out of their car and walked around to the back of the house. They were buzzed through the back door and into a small holding room, then buzzed in again, through an inner door—a system designed to insure that they hadn’t been followed. The man who ran the game, identified only as Ali, seemed to be positioning the house as a private place which only “members” could enter. Accordingly, Kebort and Von Kennel filled out membership forms. They noticed a sales-tax license on the wall—a sign of putative legitimacy. But the place didn’t strike them as legit. Inside, they found two grimy tables, where some shirtless players received massages from young women in revealing dresses. When Kebort and Von Kennel sat down to play, they found that the house took a percentage of every pot—a money-making method called a “rake,” which is commonly employed by casinos and poker rooms but not often seen in a home game.

Afterward, Kebort ruminated about Poker Social Club and its claims to legality. He had heard, generally, about the social-gambling defense. Now he looked up the law. He found that it was indeed true that gamblers could receive a “defense to prosecution” if their games met certain conditions: gambling had to happen in a private place; players had to assume equal risk (in some games, such as blackjack, this is mathematically impossible); and the economic benefits had to flow only to the winners and not to the house. It seemed clear that, by taking a rake, Poker Social Club had overstepped the bounds of the law. But Kebort found himself wondering whether a differently designed poker club might be legal.

Kebort, affable and earnest, with thinning hair, was thirty-one at the time. He had grown up in a blue-collar family in Virginia Beach; eager to make it big, he’d moved to Austin, working as a delivery driver for a catering service while launching an Internet company, which didn’t work out. His personality—ambitious yet gun-shy, daring but a little cautious—carried over to the poker table, where he was a conservative and methodical player who preferred to watch the cards and run the numbers in his head before placing a bet. Von Kennel was ten years younger, an Austin native, and the son of a successful oil-and-gas lobbyist. Cushioned by family money, he had a bluffer’s attraction to risk.

Together, the friends discussed the possibilities. Could a poker club that made its money only from membership fees and not from a rake be considered a “private place”? Would a country club qualify? How big could a “social group” be? They discussed their questions with Von Kennel’s father, Tim, drawing on his experience as a lobbyist. It occurred to them that, by lobbying, they might widen the social-gambling loophole. Kebort registered as a lobbyist; he and Von Kennel drafted a new version of the state’s anti-gambling law that would strengthen the social-gambling defense (in place of the phrase “defense to prosecution,” it substituted “exception to the law”) and, for the next two years, tried to get it adopted by the Texas state legislature. Separately, they proposed the creation of a gambling commission, which would regulate the new clubs.

The Texas legislature meets for only five months every two years—a prophylactic measure designed to prevent the passage of laws. Kebort and Von Kennel knew, moreover, that any legislator sponsoring their proposal would have to reckon with out-of-state casino owners and religious constituents, both of whom would oppose any legalization of gambling. The 2013 session came and went. Neither proposal gained traction. The next session, nineteen months in the future, felt remote.

Kebort didn’t want to proceed without more legal assurance. He was uncomfortable with the idea of opening a business in a gray area of the law. He took a job installing poker software and equipment in casinos and on cruise ships and moved to Houston. After both Sam and Tim Von Kennel attended his wedding, in 2014, he lost touch with them. In 2015, Kebort was at sea when he got an e-mail from a friend that linked to a post on a local Austin blog. It was about a new “legal poker room,” Texas Card House, that charged its members twenty-five dollars a day to play. The post described it as the “brainchild” of Sam Von Kennel.

Kebort was beside himself—it seemed to him that his friend had stolen his idea and abandoned their partnership. From the cruise ship, he called both Von Kennels; Sam sent him an apologetic text. (“I hope you won’t lose sleep or stress out over this,” he wrote.) Kebort filed a lawsuit against Sam Von Kennel, which was settled out of court. He tried to move on, and even started his own corporate catering business. But Von Kennel’s success burned him up. A cautious gambler can only be so cautious; he can’t win if he doesn’t sit at the table. In 2017, Kebort decided to open a club of his own.

As a lobbyist, Tim Von Kennel understood the importance of connections. He urged his son to consult with local politicians before opening his own club, to gauge whether members-only poker clubs fell within their legal “comfort zones.” The Von Kennels talked with officials in towns around Texas; eventually, they decided that their best bet was to open a club in Manchaca, a two-square-mile unincorporated community near Austin that was outside the jurisdiction of most local authorities. Manchaca was situated in Travis County, so Sam Von Kennel sent an e-mail to its sheriff’s department, explaining his business plan and how, in his opinion, it squared with the law. “We got an e-mail back from him saying, ‘Thanks for the heads up,’ ” Von Kennel told me. Meanwhile, he investigated the worst-case scenario and concluded that, if his club were declared illegal, he’d be charged with a couple of Class A and Class B misdemeanors, at most.