The Sunset of Si: As the Conde Nast Chairman Fades Away, His Glossy Kingdom is Losing Some Sparkle

Is There a New Newhouse in the House?

THE ELDEST SON of self-made newspaper mogul Samuel Irving Newhouse, Samuel Irving Jr., aka “Si,” knew a thing or two about aspiration. Born rich but chronically unstylish (surrounded by clotheshorses, he favors a sweatshirt), he left something to be desired as an heir apparent. As a student at Horace Mann and Syracuse, he was ambivalent about journalism, introverted and angsty, according to Carol Felsenthal’s biography, Citizen Newhouse. Living in New York after dropping out of college during his junior year, Mr. Newhouse earned a reputation as the family’s “crowned prince,” racking up bills at 21 and the Stork Club while his younger brother, Donald, demonstrated an affinity for the family business at papers like the Newark Star-Ledger.

Condé Nast was an afterthought investment that Newhouse Sr. snapped up as birthday gift for wife Mitzi in 1959, and therefore not considered a suitable perch for junior. But it was there—under the influence of elegant and brilliant editorial advisers like Leo Lerman, the man of letters whose epic house parties earned him a spot on the Mademoiselle masthead, and Alexander Liberman, the Russian-born artist whose judgment even the most headstrong editors trusted—that Mr. Newhouse found his calling. Lerman and Liberman gave Mr. Newhouse access to the kind of artistic high society from which he’d previously felt excluded. Enthralled, Mr. Newhouse threw himself into the work, serving in positions at Glamour and Vogue, reading every line of the magazines, and to the chagrin of his colleagues, showing up before dawn.

When Liberman wasn’t tearing up his editors’ pages, he was teaching Mr. Newhouse what contemporary art to hang on his walls; the collection eventually earned Mr. Newhouse a spot on the board of MoMA. Liberman also imparted one of his signature managerial gifts: identifying talent. Mr. Newhouse watched Mr. Liberman lure Vreeland from rival Harper’s Bazaar with the promise of a bottomless expense account, then made a name for himself poaching Tina Brown, the young editor of Tatler for his revived Vanity Fair.

Mr. Newhouse learned to spot gifted editors practically in utero. “It was often at such an early stage that other people didn’t even realize it was talent,” Mr. Florio said, recalling the days before Tina was Tina. “She was not all fancy and fashionable but she was wickedly irreverent, super brilliant and funny.”

He then kept that talent on its toes by being selective and unpredictable with his attention.

“I always admired that in a board roomful of talking executives that he would quietly listen to what was not being said and then provide the most meaningful comment of the meeting,” former Details publisher Steve DeLuca, now the publisher of Departures, told The Observer.

But while Mr. Newhouse’s shifting affections made Condé Nast a hotbed of competition, where alpha salesmen (and tabloid regulars) like the late Steve Florio (Tom’s older brother), Ron Galotti and Richard Beckman thrived, a series of appointments and hires over the past two years have dramatically altered the character of the company’s leadership.

At the top, there’s Chuck Townsend. An operations-minded backslapper whom sources say earned major brownie points when he streamlined the company by moving its back offices to Delaware, Mr. Townsend ascended to CEO and president in 2004 when Florio, who suffered from heart problems, stepped down. (He died from a heart attack four years later.)

Two years ago, Mr. Townsend relieved himself of the president half of his job title, handing it off to Bob Sauerberg, Condé Nast’s top consumer marketer (thank him for the subscription cards all over your apartment floor), with whom Mr. Townsend had worked at The New York Times Magazine group in the ’90s. Mr. Sauerberg was tapped just as David Carey, a brainy publisher credited with turning The New Yorker around, departed for rival Hearst and dynamic personalities like Mr. Florio (Steve’s brother) and Mr. Beckman fled in search of CEO gigs.

According to insiders, Mr. Sauerberg promised the Newhouse family board that controls the company that he would bring in millions in non-advertising revenue, while magazine publishers would continue to report to Mr. Townsend. Mr. Sauerberg’s appointment signaled a sea change. In a 2010 internal memo, he foretold “a consumer-centric business model, a holistic brand management approach and the establishment of a multi-platform, integrated sales and marketing organization.”