Southeast of the Las Vegas Strip, on the deserted fairways of Stallion Mountain Golf Club, the signs were everywhere: Billy Walters was running out of luck.

For three decades Walters, often considered the most successful sports gambler in the country, had fed on the heady exuberance of Sin City. Nowhere else was the boom wilder, the consumption more conspicuous. By the early 2000s, he’d built a business empire with interests ranging from gambling to real estate, from golf courses to car dealerships.

Like Vegas itself, he was headed for a fall.

Today, with Walters at the center of an insider-trading saga involving the golf champion Phil Mickelson, the story of how those businesses came together -- and, at times, came apart -- sketch out a crucial back story: Walters, king of the high rollers, had seen his hot hand go cold.

Like many Nevadans, Walters was hit hard when the bottom fell out of Vegas in the mid-2000s. Documents filed in connection with several lawsuits over the past decade chronicle how the financial pressures were mounting at around the time he embarked on what authorities say was a scheme in which illegal stock tips helped him generate some $43 million in profits and avoided losses.

Mickelson was not accused of wrongdoing. Walters has categorically denied wrongdoing, except in a 1982 case in Kentucky in which he pleaded guilty to a bookmaking-related charge and paid a $2,000 fine.

“Mr. Walters and his counsel look forward to his day in court, where it will be shown that the prosecutors’ accusations are based on erroneous assumptions, speculative theories and false finger-pointing,” Walters’ attorney, Barry Berke, said in response to the insider trading charges.

The third figure in the case, Thomas Davis, the former chairman of Dean Foods, has agreed to plead guilty and cooperate in the case against Walters.

Wall Street has become captivated by the Walters case, with its mix of golf, gambling and suspicious stock trading. But at heart, the Walters story is a tale of Las Vegas, that sprung-from-the-desert metropolis of high hopes and broken dreams.

Walters first made his name and fortune by bringing a Wall Street-style approach to sports betting. But over the years, even as Walters assembled a business empire that stretched from Kentucky to California, he was laying big bets on Las Vegas real estate, court records show.

As golf’s popularity exploded in the 1990s, he also spent millions on courses like Stallion Mountain Golf Club. By the mid-2000s, commercial real estate, housing and golf looked like a trifecta of disaster in Las Vegas. At the low point, about 70 percent of Vegas homeowners were underwater on their mortgages.

Compounding Walters’ problems, his gambling margins were tightening as other gamblers adopted his computer-driven ways and reduced his advantage, said David Malinsky, who worked for Walters off and on for two decades.

Courses For Sale

As the troubles on Wall Street began to spread, Walters circled his wagons. He sold Stallion Mountain, one of his four Vegas golf courses. To help the deal go through, Walters personally guaranteed the loan for the buyer. When the buyer defaulted and the bank that issued the loan went under, the Federal Deposit Insurance Corporation pursued Walters to repay $15.25 million, court filings show.

The course ended up closing for three years. That was in 2008, the year authorities say the insider trading began. By mid-2014, Walters would also sell Desert Pines Golf Club, whose greens are fashioned after Augusta National.

In a 2012 court appearance over Stallion Mountain, Dennis Kennedy, a lawyer for Walters, laid out the situation. “In 2006, and this is no secret to anybody, the economy starts to weaken, the boom is done and things are starting to go downhill,” Kennedy said. “The good times are starting to come to an end.”

Although Walters’ wealth has been estimated in the hundreds of millions of dollars, in the midst of the financial crisis he testified that he couldn’t put a figure on his net worth because a “substantial portion” was in real estate.