Hefner's Playboy Enterprises Was Always a Progressive, Family Business

Playboy was an enigma, a magazine that objectified women even as its CEO was Hugh Hefner's daughter and its politics were left-of-center.

Author:: Leon Lazaroff
Publish date:: Sep 28, 2017 10:20 AM EDT

Hugh Hefner took Playboy Enterprises Inc. private in 2011, a victim of Internet pornography.

The Chicago company, which held its initial public offering in 1971, had shrunk in size and stature as Hefner's core readers aged while younger readers, mostly male, gravitated to so-called lad magazines Maxim, FHM and Stuff, as well as porn.

Playboy was still the best-selling men's monthly in the U.S. when I covered the company at the Chicago Tribune in the early aughts. Hefner had long since decamped to the Playboy Mansion in Los Angeles, leaving his daughter, Christie in Chicago to run the publicly-traded Playboy Enterprises, housed in an elegant multistory brownstone on Michigan Avenue.

By the turn of the century, the magazine Hefner created in 1953 was no longer viewed as racy, edgy or provocative. It remained, much like Jann Wenner's Rolling Stone, a media company built around a single print publication. Wenner never took his company public, but like Hefner, he never expanded Wenner Media LLC much beyond its chief title. Earlier this month, the Wenners put their majority stake in Rolling Stone up for sale.

Hefner, who was born in Chicago in 1926, died on Wednesday, Sept. 27, at age 91 in Los Angeles. In a statement, Playboy enterprises said he died "from natural causes at his home, The Playboy Mansion, surrounded by loved ones."

Hefner's brilliance came from a calm audacity, a willingness to talk about sex, not as a taboo but as something that brings enjoyment to both men and women. His notions about sex were either too radical or simply not addressed in public, and certainly not in a magazine that featured scantily-clothed women. Hefner, though, didn't view living well as a man to run counter to feminism, whose advocates also found space in the magazine.

A monthly glossy that contained the trademark centerfold, Playboy was unlike any magazine before it, and arguably unlike anything since. At its height in the early-1970s, single newstand sales topped seven million.

In the 1990s and 2000s, though, Christie Hefner ran the company, gracefully assuming the seemingly impossible task of explaining the company's operations to would-be shareholders without making light of the fact that its content was centered around nude women, and discussions of sex.

Playboy, like Hefner, was something of an enigma. His apparent objectification of women was offset by progressive politics on race, the role of government, the American place in the world, and even women. Playboy was never Fox News.

Hefner famously published top-notch fiction and travel writing from writers including T.C. Boyle, John Edgar Wideman, Hunter S. Thompson, Margaret Atwood, Kurt Vonnegut, Ian Fleming and Ray Bradbury. His television show "Playboy After Dark" was a social trailblazer as Hefner hosted biracial parties featuring Nat King Cole and a young Nina Simone.

Playboy enthusiastically supported the Equal Rights Amendment and railed against the right-wing backlash to the social gains of the 1960s. Christie Hefner was example No. 1. When she was made CEO and chairman of Playboy Enterprises in 1988, there were few women CEOs of publicly traded companies, but Hefner himself never had doubts about his daughter's abilities.

By the turn of the century, much attention was given to Hefner's life, split among at least three girlfriends who lived at the mansion. Yet Hefner remained closely involved in the magazine's operations, routinely sending editors long emails, writing cartoon captions and contributing to the magazine's somewhat dated tradition of party jokes.

But Hefner always had a very particular vision for Playboy, and if adapting to modern norms and tastes required making substantive changes, he wasn't about to go there.

In 2002, Hefner hired Jim Kaminsky, a former Maxim executive editor, to take over the magazine's editorial operations. But that relationship quickly soured as Hefner resisted moves to remake Playboy with a contemporary redesign, graphics and expanded coverage of fashion and high-tech entertainment, notably video games and DVDs.

Kaminsky didn't fit into the magazine's culture, a company that retained a certain Midwest decorum despite content that focused on women's bodies and sex. Kaminsky was removed after two years and eventually succeeded by Christopher Napolitano, a 16-year Playboy veteran.

Though Playboy would acquire video-on-demand sites Spice Network and ClubJenna Inc., Internet porn had become too wide and too available by 2005 for the Hefners to take significant market share. Christie Hefner focused on licensing the Playboy brand, and its universally recognized bunny rabbit, to offset declines in subscription revenue and eventually, advertising sales.

Christie left Playboy Enterprises in 2009, a decision that she said at the time was motivated by the election of Chicago's own Barack Obama as president as well as her desire to do something different. By 2010, revenue had fallen to $250 million from $350 million in 1999.

After being taken private in 2011 in a transaction valued at $207 million, Playboy Enterprises moved to Beverly Hills, where it continues to publish the monthly print magazine that Hefner 64 years ago with centerfold of a nude Marilyn Monroe. These days, Hefner's son Cooper, 26, is chief creative officer.

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