Prized Trophy Wives

Billy Joel and his famously young third wife, Katie Lee Joel, split last week. From Donald and Marla to Sarkozy and Carla, VIEW OUR GALLERY and read our guide to the art of marrying up.

Tammie Arroyo / AP Photo

Tammie Arroyo / AP Photo

Billy Joel and Katie Lee Joel

When she became Billy Joel’s third wife in 2004, Katie Lee was a fledgling food critic just four years older than Joel’s daughter. Katie has yet to reach foodie superstardom or marital bliss—she was fired after hosting just one season of Bravo’s Top Chef and the couple announced last week they were legally separating. There are rumors she cheated on the Piano Man, but then again, at just 27 years old, there’s plenty of time for her to marry up again.

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Donald Trump and Marla Maples

Donald Trump married actress Marla Maples in 1993 in a ceremony at the Trump Plaza Hotel so lavish it was immortalized on the Taj Majal $5 casino chips. Unfortunately for Maples, the couple’s prenup stipulated that the marriage must last at least five years for her to receive a dime—and Trump told her she was fired only weeks before their anniversary. Maples came out of the marriage with $1 million, property, and child support for their daughter, Tiffany.

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Larry King and Shawn Southwick

Seventy-five-year-old talk-show giant Larry King must have high standards for his trophy wives—half a dozen women have tried to make it last and failed. His current wife, Shawn Southwick, is 35 years his junior and has been picking out his suspenders for 11 years. Things may be getting rocky for the couple. They’re rumored to fight often—once publicly at a restaurant in L.A.—and Southwick entered rehab last year for prescription addiction.

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Paul McCartney and Heather Mills

The best thing ever to happen to Yoko Ono’s reputation as the least loved wife of a Beatle was Heather Mills. Nearly everyone was on Team Paul during the McCartney-Mills’ nasty divorce, but Mills had the last laugh. The former model walked away from the marriage with more than $38 million, plus $70,000 a year for their daughter. The sum is far from the $200 million she originally sought, but considering the pair’s eight-year marriage, $4 million for every year married to a rock star isn’t a bad haul.

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Fred Thompson and Jeri Kehn

In the early days of Fred Thompson’s presidential campaign, The New York Times posed the pressing question: “Is America ready for a president with a trophy wife?” Although we never got a chance to find out, we did have the opportunity to ponder the grandfatherly Law & Order star’s marriage to his second, much younger wife, Jeri Kehn. The couple met in 1996, at a Fourth of July party in Tennessee, Thompson’s home state, and quickly hit it off, marrying in 2002. Despite critiques of the bleach blond beauty on the campaign trail—MSNBC’s Joe Scarborough once compared her to a stripper—the couple weathered the storm together.

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Rod Stewart and Penny Lancaster

Penny Lancaster is in Rod’s heart, she’s in his soul—she’ll be his breath, should he grow old. (Well, older.) In 2007, 62-year-old Stewart married 36-year-old former lingerie model Lancaster, wife No. 3 for the rocker. The two dated for seven years and had a baby boy together in 2005 before they tied the knot. Last month, the happy couple announced that they’re expecting another child later this year. Stewart is father to five kids from his previous relationships.

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Nicolas Sarkozy and Carla Bruni

It’s hard to say which of these two is marrying up. The French president and the Italian tire heiress/model/musician married last year less than three months after they met—and less than four months after Sarkozy divorced his second wife. Since then, Carla’s transformed into a fashion icon and the duo have become the a shining example of political and marital bliss (save for the Obamas, of course).

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Hugh Hefner and Kimberley Conrad

Kimberley Conrad managed to childproof the Playboy mansion during her 10-year union with Hef—during which the couple had two boys—but the former Playmate of the Year could do little to quell the man’s wayward heart. Since they split, it’s been all pajama games for Hefner and his slew of girlfriends, but none will win the title of Trophy Wife: He and Conrad are still legally married.

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Sumner Redstone and Paula Fortunato

When Paula Fortunato married film tycoon Sumner Redstone in 2003, she signed a prenup that would entitle her to $1 million for every year the pair remained married. After divorcing last year, the schoolteacher may have realized she undersold herself. Redstone, the chairman of Viacom and CBS, is worth a reported $5.1 billion—and likely won’t miss that $5 million.

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Aristotle Onassis and Jacqueline Kennedy

Jacqueline Kennedy Onassis may have blemished her pristine reputation with the long-winded list of suitors she entertained after JFK’s death, but who could blame her? In the case of her union with shipping magnate Aristotle Onassis, their brief and troubled marriage came with a very lucrative silver lining. In exchange for marrying, Jackie O. reportedly received $2 million for herself and $10 million from the estate after his death.

Newscom

J. Howard Marshall & Anna Nicole Smith

Several years after meeting during her topless dancing days, 26-year-old Anna Nicole Smith married 89-year-old billionaire executive J. Howard Marshall, never lived with him, and collected $450 million following his death. Anna Nicole also managed to stretch her 15 minutes of fame into a modeling and reality TV career before her own death in 2007.

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President John Tyler & Julia Tyler

Following the death of his first wife, President Tyler met future First Lady Julia when she was in her early 20s and the undisputed darling of the Washington social scene. In 1844, he became the first president to marry while in office. And while some criticized their relationship—the president was more than 30 years older than his bride—the couple remained happily married until Tyler’s death in 1862.

Patrick McMullan

Saul Steinberg & Gayfryd Steinberg

When financier Saul Steinberg married Gayfryd, a former restaurant hostess, the couple had it all. Saul made millions and financed what was once the most expensive apartment in Manhattan and Gayfryd was known for throwing lavish parties—his 50th birthday party in 1989 cost a reported $1 million and featured models posing as Old Masters' paintings. But when Steinberg had a stroke and also lost most of his fortune several years ago, a curious thing happened: Gayfryd didn’t divorce him.

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Larry Ellison and Melanie Craft

In 2004, fetching romance fiction writer Melanie Craft (author of Trust Me and Man in Trouble) married billionaire tech mogul Larry Ellison—a plot twist straight out of one of Craft’s love stories. Although she is the Oracle founder’s fourth wife—and 25 years his junior—the couple’s marriage is reportedly strong. Maybe marrying the fourth-richest man in the world is the key to a happy ending.

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Kelsey Grammer & Camille Donatacci

Perhaps Frasier Crane is a relationship expert in real life, too. In the mid-1990s, Kelsey Grammer was set up on a blind date with Playboy model Camille Donatacci, sparks flew, and the two have been together ever since. Donatacci is Grammer’s third wife, and more than a decade younger than the Emmy Award-winning actor.

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Henry VIII & Catherine Howard

Alas, no trophy wife can stay on a pedestal forever. When Henry VIII first noticed Catherine Howard, the Catholic teen was working as a lady-in-waiting for the king’s fourth queen, Anne of Cleaves. The middle-aged Henry became enamored with Catherine—calling her his “rose without a thorn”—and before long, she became queen. “The king's affection was so marvelously set upon that gentlewoman [Catherine], as it was never known that he had the like to any woman,” Thomas Cranmer's secretary, Ralph Morice, wrote in 1540. Eventually, though, Catherine—who was more attracted to men her own age—betrayed the king, and on February 13, 1542, she was beheaded.