CHAPTER 5

The story of Paris Hilton’s colorful maternal roots begins in America’s heartland, Nebraska, then shifts east to the tony town of Manhasset, on Long Island’s “Gold Coast.”

Paris’s maternal great-grandfather, “Big Ed” Dugan, was an attorney in Omaha and during the Great Depression sought and won election to the Nebraska state legislature, where he later served as chairman of the judiciary committee, and sometimes sat in as Speaker of the House.

A gregarious politico and a shrewd lawyer, Dugan was a polished glad-hander who sported colorful suspenders. He was an avid golfer, a lusty drinker, a big, barrel-chested Irishman with a red face and a full head of sandy hair that turned white but never fell out. He had the deep voice and the enunciation of a screen actor. Everything about him was bigger than life. “He always looked like he was running against Huey Long,” says a longtime family friend. “He had the body of Fredric March playing Williams Jennings Bryan and the big—big—head of Spencer Tracy playing Clarence Darrow in Inherit the Wind.”

Everyone adored his attractive, bright, and winsome wife, Dorothy Callahan Dugan, nicknamed “Dodo,” a fast-moving, quick-witted, petite woman—birdlike compared with her husband. “She dressed sharp, always had on a great hat, her shoes looked fabulous. She was chic,” observes the family friend. Paris’s maternal great-grandmother was a staunch Irish Catholic who went to every conceivable Roman Catholic mass and gave her husband four children: two sons, the kind of vanilla Ed Jr., the firstborn, and the mischievous blue-eyed Chuck, the youngest of her brood; and two daughters, the appropriately named, pretty and prim Madonna, the older of the girls by three years; and, of course, the family’s flamboyant star, Kathleen.

Always vain, big Kathy lied about her age beginning in childhood, cutting off just one year, contending to lifelong friends that she was born on April 17, 1939, instead of her actual birth date of April 17, 1938. (Years later, in 2006, Kathy Hilton was shaving years off, too. She was heard to claim she was forty-four when she was really going on forty-eight.)

By the time big Kathy came into the world, her father had become a power broker as chairman of the Douglas County Democratic Committee, which encompassed Omaha, Nebraska’s largest city, then known for a haunted former bordello and a famous insurance company, Mutual of Omaha.

When Dugan was up for reelection in the August 1938 primary, the Lincoln State Journal reported, “A number of fellow Democrats are out to get his scalp….” A scandal of sorts ensued when cronies of one of Dugan’s opponents charged that “steamroller” tactics had been used to secure his victory. He later expressed his “regret” that ballots had been handled in a highly questionable manner. Politically liberal, at least for the Cornhusker State, he once called for “a more progressive, wideawake city government.”

Several years after the Second World War ended, when Kathleen was ten, the Dugans moved east, settling in Manhasset, where Big Ed established a law practice, and he and Dodo were partners in their newly opened real estate agency. Their specialty was buying fixer-uppers, renovating then flipping them for tidy profits. The Dugans chose Manhasset because that’s where the affluent Irish Catholics from the New York City boroughs headed when they had money, while nearby Great Neck had become the Promised Land for upwardly mobile Jews fleeing the Bronx and Brooklyn for the suburban good life.

A Manhattan bedroom community, Manhasset is among the fictional backdrops for F. Scott Fitzgerald’s The Great Gatsby, a novel of decadence and excess. By coincidence, the protagonist, Jay Gatsby, had some of the same twisted values that possessed hotelier Conrad Hilton and career stage-mother Kathleen Dugan Avanzino Richards Catain Fenton throughout their lives.

The Dugans were drinkers and party people, so Manhasset was a perfect setting. Bars lined one of the main drags, Plandome Road, a half-mile stretch in a town that consisted of only four square miles. The place even had a drink named after it—“The Manhasset,” which one wag described as a Manhattan with more alcohol. As Jane Hallaren, big Kathy’s closest friend from childhood, observes, “There wasn’t a parent in town that I can remember who wasn’t an alcoholic. Parents were saying terrible things about each other. They had nasty, vituperative relationships. There was animosity and cleverness. It was very Irish.”

The Dugans fit right in.

Dodo Dugan enrolled skinny, cute, precocious Kathleen, with her mop of spectacularly thick, frizzy-curly dark auburn hair, and her teasing green eyes, into classes at the newly opened grammar school at St. Mary’s Roman Catholic Church on Northern Boulevard.

Always in control, always in everyone’s face, the Dugan girl quickly became the leader of an A-list clique at St. Mary’s—a small group of snarky, sanitized grade-school “Heathers” who sported a uniform of blue jackets and skirts, white blouses, and blue-and-white saddle shoes.

When little Janie Hallaren, whose parents had moved to Manhasset from the mean streets of Brooklyn, showed up for her first day of school in the fourth grade, Dugan made it clear to her who ran the show.

“I’ll never forget our first meeting,” says Hallaren years later. “The nun tells me to go down the aisle. Kathy was sitting in the first seat in the aisle and had organized some girls behind her and they fluffed their hair and eyed me as I walked passed them. Kathy turned around and looked at me like, ‘You’re not going to make it here,’ and the four girls in succession behind her did the same thing. I was a very tough kid, so I waited for her outside after school and I said, ‘You’ll never do that again,’ and I beat the shit out of her. That was that.”

A few days later, Kathy, impressed with and respectful of Hallaren’s toughness, invited her into her gang.

On one occasion, the two new bosom buddies met at the Dugan house, and another neighborhood girl showed up. All three went down into the basement and were listening and dancing to Kathleen’s record collection.

“All of a sudden Kathy whispers to me, ‘Look, Janie…look, Janie…Look…’ And she’s pointing at the other girl’s beautiful curly brunette hair. And I look and Kathy had spit all over this girl’s hair. I could see gobs of spit. And Kathy was giggling. Still, today, I think of that scene and I get the willies. I went upstairs and said to Dodo, ‘I have to go home now,’ and I called my mother and told her to meet me at the top of the hill. ‘I’m not staying here.’”

The curious incident foreshadowed acts even more bizarre and violent that Kathleen would commit later in life—even against loved ones. If there ever was a real-life Rhoda Penmark—the evil child in The Bad Seed—in the making, it was Kathleen Dugan.

Because she was not much of a student academically and had behavior issues, the future maternal grandmother of Paris Hilton bounced from one school to another. From St. Mary’s the Dugans, who had a reputation as liberal parents—maybe too liberal—shipped her off to a Catholic girls’ boarding school, the Academy of Saint Joseph, in Brentwood, a town on Long Island further east from Manhasset. But she couldn’t abide by the rules or handle the rigid academic standards, so the next stop was Marymount, in Tarrytown, New York, where her sister, Madonna—called Donna—was also a student, though three years ahead. At Marymount, Kathleen’s singing and acting talent came to the fore, and she began thinking of herself as a future star. She took speech lessons and joined the drama club.

“She loved the movies and she sang beautifully and she loved to doll up,” says her sister. “We were both in The Mikado. Kathleen had a very nice voice and evidently mine wasn’t that bad, but it wasn’t as good as hers.”

Aside from her love of acting onstage, and acting out in public, Kathleen Dugan despised Marymount. She missed being home and having unlimited freedom to do as she pleased. As her sister notes, “Kathleen was very unhappy being away. She wasn’t used to being dictated to.”

Back home she enrolled at Manhasset High School, an archetypal suburban 1950s teen scene where she was reunited with Jane Hallaren, who had just come into the school herself after being expelled from St. Mary’s for participating in a beer party, an expulsion she claims was unfair. Kathleen was inducted into a tight-knit clique of Hallaren’s friends—Christina Demaitre, and preppy Martha Hanahan. “Janie introduced me to Kathy, who was a total lunatic,” says Demaitre, who was a cheerleader. “Kathy was different from everybody else.”

In an era when girls wore circle pins, Peter Pan collars, crinolines, bobby sox, and penny loafers, Kathleen Dugan was a dyed-in-the-wool fashionista, just like her granddaughter Paris would be. She wore cat’s eye sunglasses and lucite and rhinestone Springolators with four-inch heels, the kind Marilyn Monroe wiggled on. Kathleen had even introduced boudoir wear into her style.

“She goes out one day and buys this pink brocade bathrobe that’s zipped up the front and she bought a red waist cinch as a belt,” recalls Hallaren. “It was something you would wear for lounging. But she wore it out. She said, ‘Nobody will know. It looks like a gorgeous gown—and I’m wearing it!’ Everything she did was ballsy.”

Demaitre’s European-educated, intellectual mother pegged Kathleen as a study in shallowness and narcissism. “Kathy thought she was so glamorous. She was very outrageous, self-involved, interested only in what she was doing,” Demaitre says, still aghast years later.

Kathleen was invited to join Alpha Theta Alpha, the “Animal House” of sororities at Manhasset High, and most of the group’s soirees were thrown at the Dugans’ because no other rational-thinking Manhasset parent would have permitted a hundred or so beer-guzzling, scotch-swigging, hormone-seething teenagers to take over their gracious homes for an evening. “I’m sure many of us had too much to drink and were a complete danger to ourselves and the rest of the world as we drove away,” notes Hanahan.

“Her parents were remarkable,” says Demaitre, still dumbfounded at their permissiveness years later. “The whole house would be full of people, and they’d just go quietly up the stairs and go to bed. It was like Kathy was running the house.”

Now that she was in a public high school, Kathleen was surrounded by good-looking, strapping fellows from fine Manhasset homes. She felt as if she had died and gone to heaven, although anything to do with sex was verboten. Despite her outrageous demeanor and provocative style of dress, friends like Hanahan and Hallaren contend that Kathy was strictly a tease with boys and extremely inhibited about sex. However, one young man had caught her fancy, and she would pursue Bob Conkey relentlessly, albeit unsuccessfully, into adulthood, even while both were in marriages, even to the point where he began to think she was stalking him, even causing his wife, who was CBS anchorman Walter Cronkite’s secretary, to suspect hanky-panky.