Jill Kelley seen as a wanna-be in South Tampa society

Published Nov. 18, 2012

TAMPA — She wanted the Cattle Baron's Ball to go black tie.

But that just isn't how things are done in South Tampa society.

Tuxedos come out for Ye Mystic Krewe of Gasparilla's coronation ball, but the Cattle Baron's Ball is intractably Western — Stetsons, Tony Lama boots, pearl-button shirts. Black ties at the Cattle Baron's Ball would be as silly as Hawaiian shirts at the elegant Pavilion gala.

Jill Kelley might have known so, had she grown up south of Kennedy Boulevard, gone to Plant High School, come out as a debutante, paid dues to the Junior League and had a daddy who teed off at the Palma Ceia Golf & Country Club.

A decade ago, Kelley was an arriviste, a new-in-town doctor's wife looking to climb rungs on Tampa's social ladder.

The annual cowboy ball to raise money for cancer research could have been her way up.

She offered to chair the event if she could turn it into a formal affair. She went so far as to mail out save-the-date cards with a new dress code.

Thank you, no, organizers said. It would remain hoedown casual.

With that, Kelley had overstepped an invisible line in a city where boundaries were set so long ago no one need even discuss them.

• • •

She was a spirited, attractive, sexy-dressing socialite who partied with the powerful. She was also a name-dropper who wanted to be somebody in Tampa.

Though probably not like this.

As the world now knows, Kelley's complaint to an FBI friend about emails accusing her of flirting with then-CIA director David Petraeus ultimately exposed his extramarital affair. It also led to revelations that she traded personal emails with Marine Gen. John R. Allen, commander of military forces in Afghanistan. Those exchanges are now under government scrutiny.

And so, with her twin sister, Natalie Khawam, Kelley, 37, is near the center of a scandal that has everyone peering at Tampa society — with some national wags snarkily questioning its very existence.

In truth, this city has the sort of rigid social structure that is backbone to many a Southern town. Here it is born of families made rich by cigars, cattle and citrus and steeped in the tradition of powerful men who dress up now and again as pirates.

The old family names adorn tall downtown buildings, bridges and landmarks. Lykes. Frankland. Lowry.

And then there are the other layers.

"Most of South Tampa society," says former mayor Sandy Freedman, the first woman to run the city, "is the Gasparilla krewe, the Yacht Club, Palma Ceia. It's lots of people who have grandfathers, great grandfathers, third, fourth generation.

"Then there are people who move to town who are affiliated with banks and big companies, and they're immediately welcomed."

And then, the wanna-bes.

"There are some nice wanna-bes who behave properly and wanna-bes who are a real pain. I think these people" — Kelley and sister Khawam — "are, without question, wanna-bes.

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"Tampa's answer," Freedman says, "to the Kardashians."

• • •

South Tampa, the society whose approval Kelley sought, occupies a mere 15 square miles in a county of 1,000. Part of a peninsula, it allows views of two bays: Tampa Bay to the west and Hillsborough Bay to the south, from porches of grand mansions on Bayshore Boulevard.

Kennedy Boulevard, so named after the president's assassination, is its northern border and invisible boundary. People boast of living the bulk of their lives SOK, or South of Kennedy, center of the social universe.

"I would say South Tampa society is just like any Southern town society, except more extreme, more weird," says Patrick Manteiga, publisher of La Gaceta, Tampa's trilingual newspaper. "It's got more sex involved. It's got more cliques involved."

The roots for Tampa society were planted more than a century ago, when a newspaper society reporter set out to drum up interest in a ho-hum May Day festival. Lifting from a pirate tale, she teased readers to turn out for an impending invasion by a mutinous (and nonexistent) Jose Gaspar. Residents who came watched 50 businessmen persuaded to put on masks and play along.

Crowds have come ever since, making the annual march down Bayshore Boulevard one of America's biggest parades, a beer-soaked, bead-tossing tradition complete with a grand pirate ship.

The first Gasparilla king and queen were crowned that night in 1904, creating what remains Tampa's signature social club, Ye Mystic Krewe of Gasparilla.

Their descendents — bankers, lawyers, politicians — make up the current 800 all-male roster. Even now, their wives' social calendars revolve around krewe tradition, like the Captain's Ball (dress code: pirate formal).

Back then, women started a Junior League and later the Chiselers, so named when they helped chisel paint off tiles at the old Tampa Bay Hotel. They took off their white gloves to play bridge and golf. They sailed, played tennis and showed horses. Children who grew up watching their fathers paint on pirate scars became pages, debutantes and courtiers.

With piratehood largely inherited, integration was not a priority. The Latin community started its own krewe of prominent men, the Krewe of the Knights of Sant'Yago.

But in 1991, with the Super Bowl headed to town during Gasparilla, the NFL raised questions about the all-white Ye Mystic Krewe. Unwilling to bow to pressure, the krewe called off the parade that year.

A few black men were subsequently asked to join, and the pirate ship Jose Gasparilla sailed again. Since then, dozens of new krewes have stepped up to include gay, female, Hispanic and African-American revelers.

"The good thing is Tampa is a very different place than it was when I got here," says Mayor Bob Buckhorn. "It is far more embracing, far more diverse and far more open because of the influx of many new people."

• • •

Tampa society still means money — old money, new money, and people who lack it yet flaunt it nonetheless. The Kelleys hosted gatherings even as their mortgage went unpaid. They hired bartenders who poured soft drinks for kids' birthday parties.

And people notice. Too-eager excess stands out like a rhinestone toilet or a home decorated with all-new furniture. There should always be an ugly lamp handed down from Granddaddy or a secret room kept locked from guests.

"We were a small Southern city for a long time," Buckhorn says. "As a result of that, all the families grew up together and knew each other and had been involved for generations.

"I picked it up pretty quickly. You trace the pedigrees," he says. "You know who are posers and who are legitimate."

For a scorecard of the players, cast eyes on an invitation list to one of the galas.

When Gasparilla King David A. Straz Jr. hosted a formal dinner in October, the program's list of Ye Invited Guests placed a small asterisk beside every former king or queen. There were 87 invited royals.

They feasted on venison tenderloin, after a duck appetizer and baby arugula salad, listened to an opera diva, then retired to the Riverwalk for champagne and cigars beneath a sky lit up by fireworks just for them.

Some of the same faces appear at charity fundraisers. These deep-pocketed A-listers spend big at auctions and their attendance is courted. Some do not flash money but come through quietly when needed.

"If you are brand new to the community, and you want to get into that echelon, you do need to meet high charitable expectations," says Kasey Shimberg Kelly, a South Tampa native and member of the Shimberg clan that has donated millions to various causes. "It definitely requires a hefty commitment of time and or money. If you're able and fortunate to come in with an open checkbook, you're welcomed with open arms. With cash comes bigger exposure because everyone knows who you are — the diamond sponsor, not just a table host."

The 82-page book of auction items from the last Cattle Baron's Ball included a chance to fly off with the Tampa Bay Lightning on an away game, a wine tour to Italy, a Yankees weekend in New York, a trip to the 2013 Grammys and a week at the Jimmy Buffett house in Key West.

Caterers get $50 to $150 a head to feed crowds large enough to require arenas and party halls — TPepin's Hospitality Centre or A La Carte Event Pavilion — or small enough to take over homes and back yards.

"We've probably done parties at a good quarter of the homes on Bayshore," said caterer Kim Bailey, amid plans for a Thanksgiving fete for 80.

He recalls planning an event for a woman with more than 200 guests and asking her about renting dishes. "And she opens up a room, maybe 20 by 20, and she has everything we need, china, glassware, a full room of it."

• • •

Jill Kelley wanted to live with her doctor husband and three children on Bayshore Boulevard, a 4 1/2 mile waterfront ribbon of concrete and the city's prettiest and most prestigious address. For months she knocked on doors, even suggesting to some residents it was time to downsize.

The Kelleys bought a charming brick mansion. She attended teas, luncheons, fashion shows, cocktail parties and galas. But insiders didn't consider her one of them. They say she tried too hard. She should have gone slower.

The Times made several attempts to interview Kelley for this story. The inquiries were referred to a publicist, who declined requests for comment.

Kelley eventually turned her sights a half-dozen miles south of her Bayshore mansion, past the Yacht Club where everyone who's anyone has been served eggs Benedict or a Bloody Mary. There sits the tip of the Interbay Peninsula, home to MacDill Air Force Base.

Tampa's military presence is as much a point of pride as its thriving state university or its world-class international airport.

The base and its officers became a draw for Kelley. They weren't kings and queens, but they were generals. They ran the world.

Insiders say 99 percent of MacDill's big-name local boosters sincerely support the military in their midst.

"We've been there lots of times to parties and meets-and-greets at the base," says Beverly Austin, Tampa resident for 50 years and wife of pioneer developer Al Austin. "We try to be respectful and not overwhelm them. They're the greatest citizens we have."

Then there are people with money, or at least the appearance of money, whose status can only rise by forming friendships with four-star generals.

Mark Rosenthal — like Kelley, a civilian liaison to MacDill — enjoyed learning about the military from Petraeus and other officers. But Rosenthal said Kelley seemed more interested in talking about herself.

He thought it odd that she communicated with Gen. Allen directly instead of with his wife. That would have been proper protocol, which matters in the military, says the retired Tampa developer who has connected MacDill with Tampa residents for about five years.

The military officers remained polite to Kelley and her sister, Rosenthal says, even when the two women were loud and boisterous at parties and dressed inappropriately.

"It's a disaster what they've done to the military," he says. "The sad thing is, that military has been open to the people in Tampa and this one bad bunch could ruin it for everybody."

Staff writer Jessica Vander Velde and researcher Caryn Baird contributed to this report.