The peep show prince of metro Detroit's empire is crumbling following costly legal fights, a government crackdown and the flood of free Internet pornography, which have drained millions from the lifestyle of a little-known entrepreneur.

Court records and interviews portray Plymouth Township resident James Olsafsky as a publicity-shy porn titan clinging to a shrinking corner of the U.S. adult entertainment industry.

In recent years, Olsafsky had ties to a network of about 40 adult bookstores and distribution companies stretching from the West Coast to Rhode Island and including five in metro Detroit named either Intimate Ideas or Front Page.

Olsafsky, who once reaped a profit of about $3 million a year from the chain, recently lost a stake in 19 stores across the South following a fight with partners. The full scope of Olsafsky's current and former business holdings is unclear, however, because his financial interests are a maze of limited liability companies and some ventures held in relatives' names.

Cracks in Olsafsky's empire, however, are revealed in a series of state and federal court filings — including a November federal lawsuit filed by a peep-show repairman — that offer insight into the life and career of a controversial figure.

The filings show a businessman saddled with a multimillion-dollar court judgment amid a fundamental shift to online pornography in the 30 years since Olsafsky, now 67, took control of a distribution network from an infamous, pioneering pornographer.

Now, rivals have absorbed revenue that once went in Olsafsky's pocket.

"Pornography is free now," said Tom Nardone, whose Troy-based PriveCo Inc. sells adult products online. "That business has really disappeared, especially with the advent of the Internet. There's only a few still around."

Years ago, Olsafsky was awash in cash. He had so much money that he bought a $60,000 timeshare in Mexico and never visited. So much cash that his $3 million, 19-acre Malibu estate overlooking the Pacific Ocean had its own name — Villa Vista Oceano — and celebrity boarders. Mariah Carey leased it, and alternative rock band Stone Temple Pilots recorded the album "Shangri-La Dee Da" there, according to a 2007 Los Angeles Times article. Olsafsky had so much cash he gave an ex-wife $20,000 a week in alimony just to go away.

All thanks to peep show booths and adult bookstores, a relic of metro Detroit's economic underbelly.

"That man represents millions of unsatisfied lives. It's a tragedy he was so successful," said former Ypsilanti Mayor Cheryl Farmer, who battled Olsafsky years ago while trying to close his adult bookstore.

Olsafsky wouldn't comment to Crain's about his career or recent troubles.

"He's had a fascinating career, but with that came a lot of pain," wife Linda Olsafsky toldCrain's. "He is burned out."

The porn career of James Olsafsky dates to at least 1971. That's when he was living near Cleveland, working as a bookkeeper for Reuben Sturman, who was considered the world's largest distributor of pornography in the 1980s.

Sturman owned a far-flung empire, including 13 businesses in Michigan, which generated millions. Officially, Olsafsky was bookkeeper for about 20 bookstores from 1971 to 1984. Unofficially, he was ordered to destroy records subpoenaed by a federal grand jury, according to Olsafsky's testimony in a federal court case.

By the mid-1980s, with the feds closing in on a tax evasion indictment against Sturman, Olsafsky took over the Cleveland porn king's Michigan distribution network, according to the 2003 book Reefer Madness: Sex, Drugs, and Cheap Labor in the American Black Market by investigative journalist Eric Schlosser.

"We basically watched while (Sturman) tried to spin off the business enterprises to various managers and trusted people," Internal Revenue Service investigator Richard Rosfelder toldCrain's. "His expectation was they would continue to funnel money back to him."

Olsafsky was a key government witness after Sturman was charged in 1987, testifying that Sturman hid money in Swiss bank accounts and that Olsafsky was ordered to destroy documents. The trial ended with Sturman convicted and sentenced to 10 years in prison — where he would die in 1997.

"I think everybody went on their merry way," Rosfelder said. "Apparently, Jim learned well and was a smart enough guy to parlay what became his into something very lucrative."

Olsafsky's shops sold pornographic movies, magazines and offered coin-operated peep show booths where customers could privately watch videotaped porn.

The stores soon ran into trouble — trouble that later helped Olsafsky limit Michigan's obscenity laws.

In October 1991, police officers launched an undercover operation and raided stores in Waterford Township, Pontiac and Hazel Park. Officers seized explicit magazines and videotapes and traced the products to Olsafsky's warehouse in Livonia, where they found magazines and videotapes.

Olsafsky fought back.

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In 1993, he won when the Michigan Appeals Court ruled the state's civil obscenity law was overbroad and unenforceable.

Olsafsky's empire soon grew and his lifestyle reflected riches generated by the XXX trade.

He bought a $60,000 timeshare in Los Cabos, Mexico, around 1990 — then never visited it, according to court records.

In 1997, he bought Villa Vista Oceano. The gated estate features a 7,000-square-foot Mediterranean villa with a pool, tennis court, gym, arboretum and horse stables, according to a real estate listing.

By then, Olsafsky made enough money to buy a Villa Vista Oceano every year.

He owned a stake in 22 adult bookstores, two wholesale companies and real estate, according to court records. In 1998, he earned more than $2.7 million.

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