Robert Charles Joseph Edward Sabatini Guccione, the founder and former chief executive of Penthouse magazine, was a man who took calculated risks. Some paid off, others cost him millions.

The Brooklyn native originally planned to become a Catholic priest, and even attended the seminary, but dropped out when puberty caused his hormones to kick in. He wed at 18 and fathered a daughter named Toni, but the marriage foundered, and Guccione headed to Europe to work as a painter and journalist. He wed a second time, to British singer Muriel Hudson, and fathered four more children (Bob Jr., Nina, Anthony and Nick); however, his habit of amassing large debts ended that union.

Unable to make a decent living as an artist, Guccione next decided to try his luck at pornographic publishing. With less than $2,000 on hand, he launched Penthouse in 1965 as a low-brow competitor to Playboy, the glamorous adult magazine run by Hugh Hefner. In the magazine’s early years, Guccione couldn’t afford professional talent so he ended up photographing most of the models. He enjoyed pushing boundaries with each spread, and bragged about his decision to publish “lesbians, threesomes, full-frontal male nudity, erect penises.” Tabloid journalism, a racy letters column and beautiful centerfold models known as “Pets” helped Penthouse find an audience in the U.K. and the U.S. At its peak in the 1970s, Penthouse reportedly sold nearly 5 million copies a month.

Penthouse also inflamed the public’s passions with its controversial offerings. Feminists and conservatives blasted its raunchy content. In 1984, the magazine ran a sexually explicit pictorial of Vanessa Williams, the first black woman to win the title of Miss America. The pictures cost Williams her crown, but generated $14 million in profit for Guccione.

A year later, Guccione offered the serial killer known as The Unabomber a monthly column in Penthouse if he promised to stop taking lives. Ted Kaczynski, a.k.a. The Unabomber, gave Guccione permission to print his unedited manifesto, but with one caveat: he reserved the right to murder one more person. Guccione refused to take the bait. A tip from Kaczynski’s brother led to his capture in 1996. Kaczynski later pleaded guilty to 10 counts of illegally transporting, mailing and using bombs and three counts of murder, and was sentenced to life in prison with no possibility of parole.

Penthouse began to lose readers in 1986 when U.S. Attorney General Edwin Meese’s Commission on Pornography issued a report attacking the adult entertainment industry, prompting newsstands and convenience stores to pull the publication from their racks. In the 1990s, sales took a hit as subscribers began to seek out free porn and X-rated video online.

Although Guccione was once listed in the Forbes 400 ranking of wealthiest people ($400 million net worth in 1982), bad investments and risky ventures eventually cost him much of his fortune. He spent $17.5 million producing an X-rated version of “Caligula.” The 1979 film, which starred Malcolm McDowell, Helen Mirren, John Gielgud and Peter O’Toole, tanked at the box office. He tried to open a $200 million casino in Atlantic City but a stubborn resident and a licensing issue stalled construction for years. Guccione was forced to pay $45 million in back taxes in 1985 and another $80 million in 1992. And in 2003, General Media, the publishing arm of Penthouse International, declared bankruptcy.

His personal life was no less tumultuous. Guccione’s third wife, Kathy Keeton, an exotic dancer who was entrusted with the financial management of his publishing empire, died in 1997 from breast cancer. Her death affected him deeply. He wed a fourth time in 2006, to exotic dancer April Dawn Warren, but spent much of their marriage battling throat and lung cancer. Relations with some of his children also fell apart over money matters. In recent years, soaring debts forced Guccione to sell off many of his possessions, including an impressive art collection and his 27-room mansion in Manhattan.

Guccione died on Oct. 20 of lung cancer. He was 79.