When Did Socialite Become an Insult?

From Brooke Astor to Jill Kelley. How far they have fallen.

Also in Slate, see our exclusive trailer for the new Real Housewives of the Pentagon.

Jill Kelley leaves her home on Tuesday in Tampa, Florida.

Jill Kelley, socialite.

Photo by Tim Boyles/Getty Images.

The other other woman at the center of the Petraeus scandal, Jill Kelley, is broadly being described by the press as a “socialite,” for lack of a better word. What else do you call a woman with a glamorous lifestyle whose unpaid “job” it is to drink and gossip with powerful friends?

But socialites aren’t what they used to be. If Brooke Astor were still alive, she’d be scandalized by how much the breed has declined. Once upon a time, a socialite was a woman with money and power, a type you might gossip about but still be desperate to get invited to her parties. Now socialite is a hollow role aspired to by debt-addled pretenders and people who are angling to get their own reality TV show. Socialites nowadays are the Real Housewives of OC, living high on the verge of foreclosure, or Michaele Salahi, crashing a state party dinner and looking so much like she belongs that security just lets her in. Now, anyone can be a socialite if they can fake it long enough. What’s amazing is that anyone aspires to be one anymore.

Perhaps the best you can say of Kelley—whose FBI complaint led to revelations of spy chief David Petraeus’ extramarital dalliance with his biographer Paula Broadwell and whose own “potentially inappropriate” communications with Marine Gen. John Allen are now being scrutinized—is that she’s a self-made woman. One acquaintance labeled her a “Tampa Kardashian.” Among the city’s elite, she projected wealth and authority, even though her and husband Scott Kelley’s millions appear to have been a mirage, and her positions, without pay or responsibility, appear to have been primarily designed to coddle her ego.

In news stories, which offer richer detail by the day, Kelley, 37, comes across as a modern-day Becky Sharp, throwing “champagne-and-caviar” parties for Petraeus and other bigwigs even as banks filed suits against her and husband Scott, claiming they owed close to $4 million on their 5,500-square-foot home and a downtown office building. She and Scott, a cancer surgeon, as well as her twin sister, Natalie Khawam, founded a cancer charity and promptly bankrupted it. Khawam is in debt to the tune of $3.6 million and has filed for bankruptcy. And yeah, the sisters did a reality TV stint on the Food Network.

The new breed of socialite is rather more flashy than the old, less couture and more spring-break girl all grown up. The twins wear body-conscious dresses in bright colors, cropped short to shows miles of long, tanned leg. They pose almost identically in photographs, knowing how their images will play on the pages of Tampa Bay Magazine—bodies turned for slimmer profiles, chins down, heads cocked to the side. Never not ready for the camera.

This type of socialite builds her social credentials with the human-relations equivalent of a Ponzi scheme. She uses connections with important people to trade up to more connections with important people, hiding the fact that her initial ticket in is a fraud. Thus, Kelley went shopping with Holly Petraeus. She dined with Charlie Crist. (Natalie was no slouch, either—she name-dropped Sens. John Kerry and Sheldon Whitehouse.) Kelley had special permission to visit MacDill Air Force base in Tampa without an escort (now revoked). She was made an unpaid “honorary ambassador” to U.S. Central Command (and then tried to rope the command into assigning staff to help her organize parties). She was made an “honorary consul” of South Korea, a “largely symbolic” post that the Los Angeles Times reports she tried to milk for $80 million. Kelley also invoked this status when she called police Sunday to complain about people on her lawn, telling the dispatcher that she should have “diplomatic protection.” Even as the fraud was on the verge of collapsing, she was trying to trade up.

The term socialite has long carried a small whiff of derision. The term first shows up on the 1909 Oakland Tribune society page, describing one such creature, a “fair Nellie,” as the quintessence “of desirability”—“we bruised our shins to be in her proximity.” By the 1920s, professional models were complaining that socialite “rich girls” were taking their jobs for the fun of it. During the Great Depression, socialites were dropping thousands on polo-playing ponies.

Still, socialites did things. Gertrude Vanderbilt Whitney founded the Whitney museum. Alva Belmont was a suffragette. Packaged-food heiress Marjorie Merriweather Post was a savvy businesswoman. While some worked, many wielded more power through their wealth and connections than they would have at any day job. And being a socialite was not just about who you knew, but who you didn’t care to know. It meant having entrée to an exclusive club and controlling the invitations, forever scrutinizing outsiders whose money and names were not quite old enough.

And then things changed. Women started working, and the world respected them for it.  Having your own TV show (Oprah) or becoming an executive at a cool company (Sheryl Sandberg) is what allowed you to hand out first-class invitations. (Heck, even Paris Hilton works.) Sally Quinn, the hybrid reporter/socialite, declared the end of the Washington hostess in 1987, though as recently as this year she was still bemoaning the disappearance of the old social elite, writing that all the power had passed from the classy old guard (people like her) to people who merely had money.

The strangest thing about all these revelations is that the Kelleys and Khawam were able to form such close connections with two men whose bread and butter is intelligence, confidentiality, and careful judgment. Forwarding those “jealous” emails from Paula Broadwell was not the first sign that the sisters did not have the old guard socialite’s discretion and instinct to keep the secrets in the family. According to police records, the Kelleys were constantly calling to complain about “bike thefts, burglaries, prowlers and harassing callers.” Natalie Khawam once claimed that she was being threatened and videotaped by a “terrorist sympathizer” hired by her estranged husband. In a custody battle, a judge pronounced her “psychologically unstable” and described her as lacking “any appreciation or respect for the importance of honesty and integrity in her interactions with her family, employers and others with whom she comes in contact.” And meanwhile, Khawam managed to get Allen and Petraeus to both write letters on her behalf.

What was obvious to the judge was invisible to Allen and Petraeus—perhaps all they saw was the glamour. Perhaps they, too, were seduced by getting invited into the exclusive club.