out of a Chicago mobster with Kennedy ties getting shot in the head in January of ’46 in front of the Tradewinds on Rush Street.
That Joe’s middle son Bobby had made a name as a racket buster on the McClellan Committee was a source of amusement to cops and disgust to crooks. In fact, Zwillman’s 1959 suicide (or was it a mob rubout?) happened in the shadow of a Bobby Kennedy subpoena-ironic coincidence, or cause and effect?
Anyway, I knew Jack only slightly, although a job I did had made me popular with him-I was the guy Old Joe chose to “take care of” the president’s first marriage.
In ’47, the first-term congressman wed a Palm Beach socialite named Dulcie Something, a quickie justice-of- the-peace deal that was probably one part impulse and two parts gin, Gordon’s or otherwise. Within days, the marriage disintegrated, and Old Joe hired me to handle it. I found a local Palm Beach attorney with the right (wrong) reputation, and together-with money and matches-we gave Dulcie amnesia and made the wedding documents in the local courthouse disappear.
Shortly after, I got a nice phone call from Jack, thanking me, and he expressed his gratitude in person a few times, once in Chicago at a Palmer House event, again in Vegas when we were both guests of Sinatra at a show at the Sands. Later, Jack was on the Rackets Committee, too, but not involved to the extent Bobby was, and in that capacity never mentioned or even vaguely referred to what I’d done for him. And for two grand.
We’d most recently socialized not long before he won the presidency-September of 1960, when he was campaigning hard to win Illinois, which of course he did, thanks to Sam Giancana, Mayor Daley, and a bunch of people in graveyards around the greater Chicago area whose civic duty had them voting above and (from) beyond.
One of JFK’s biggest supporters in Chicago was Hugh Hefner, perhaps America’s most unlikely Horatio Alger story, a shy would-be cartoonist who became the sophisticated king of a twenty-million-dollar empire. Hef, only in his early thirties, was the scourge of moralists and the envy of thirteen-year-old boys of all ages.
He had basically taken the format of the slick men’s magazine Esquire, where he’d once held a lowly sixty- buck-a-month position, and to its big-name fiction and fashion tips and automotive write-ups and sexy cartoons added a younger, more rebellious touch…
… and a monthly nude pinup-the centerfold spread of supposed “girls next door,” the likes of whom would have kept most healthy men at home and not seeking fame and fortune in the big city like Hef.
The first “Playmate” had been Marilyn Monroe, but Hef had merely bought magazine publication rights to one of her infamous calendar photos. Nonetheless, Marilyn’s image on the cover-and in the sideways pinup-made the first issue a smash back in ’53. Now, less than ten years later, Playboy was outselling Time and Newsweek.
I take the liberty of calling Hugh M. Hefner “Hef” because we were friendly, if not friends. For five years now, the A-1 Agency had been on a fifteen-hundred-dollar-a-year retainer for Playboy, which got hit with threats, scams, and various lawsuits that required immediate access to the kind of investigative services we offered. Not a year had gone by that we hadn’t eaten up that retainer and more.
The Playboy Mansion, as Hef called it, was on North State Parkway, two blocks from Lake Michigan on the Chicago Gold Coast. The iron-fenced turn-of-the-century four-story brick-and-limestone structure, once a showplace of the rich and famous, had by the Depression become a shabby apartment house. Just a year before, Hef had shown me around the huge, unoccupied and quite dingy structure.
“Has possibilities, don’t you think?” Hefner-lanky, dark-haired, almost handsome, with a Lincoln-esque, awkward air-seemed always to be puffing a pipe. Otherwise he looked like a kid in an overcoat over lounging pajamas and slippers that were dangerous in this place. We’d jumped in a cab from his office, where he worked odd hours and had a bachelor apartment. It was a Sunday in December and cold as hell.
“It won’t be cheap to renovate,” I said. “It’s like a small hotel.”
“I love Rodgers and Hart,” Hef said with a grin. Pipe in his teeth, he looked like a skinny and very lost Mark Trail. “Let me show you the crowning touch.”
That turned out to be a second-floor ballroom with decoratively carved woodwork, a marble fireplace, massive French doors, open beams, pillars, and huge bronze chandeliers.
“Imagine this wonderful space,” Hef said, “ and forty rooms.”
“Enough for Ali Baba,” I said, “and all his thieves.”
He laughed, maybe even finding that funny. “So… can you fix me up with security, while we’re remodeling?”
“Sure. I have people we use.”
Within months, as the new decade began, the mansion took shape. He added suits of armor to guard either side of the entrance to the grand living room that the ballroom became, adorning its paneled walls with massive modern art pieces by de Kooning, Pollock, and others (seemed the boy cartoonist preferred abstract expressionism these days).
The bedroom and apartments were refurbished lavishly and most had fireplaces. Hef’s master bedroom had a round, rotating bed, its headboard home to controls for the latest in TV and stereo. He told me he got more work done there than the office; I said, “I’ll bet.”
Below the former ballroom he put in a palm-bedecked swimming pool, with a small, waterfall-protected, recessed grotto. A sunken bar whose primary light source seemed to be backlit framed centerfold photos provided a massive window on underwater swimmers, who were mostly shapely young women in-and sometimes out of- bikinis.
I was by no means a regular, but the weekly parties-starting in the spring of 1960-were attended by several hundred guests: show business types, upper-echelon magazine staff, pro athletes, plus occasional politicians, novelists, poets, journalists, and other liars.
And of course beautiful young women, Playmates who now worked for Hef’s company, some as receptionists and secretaries, others as traveling Playboy PR ambassadors, quite a few employed as “Bunnies” at his new, very successful Playboy Club, on nearby Walton Street, for key-holders only. The Bunnies wore one-piece satin swimsuit- like outfits, lots of bosom and thigh exposed, plus cute rabbit ears, bow tie, cuffs, and a tail fluffier than Bugs Bunny’s.
I picked up a few at these parties, and dated one or two. Some were stupid, some smart, some in-between, but all were lovely and most were cooperative-neither hookers nor nymphos, just girls looking for opportunities. Marriages and movie contracts and various other arrangements blossomed for them at the mansion and the club.
Though Hefner spent a fortune on food, drinks, and help at his weekly shindigs, the entertainment cost him nothing, coming courtesy of his showbiz guests-folksingers and stand-up comics from Mr. Kelly’s, always, big-name acts over from the mobbed-up Chez Paree, usually.
Right now, September of 1960, I was seated on a sofa next to Hef, who was in a continental-style tuxedo, pipe going, occasionally sipping a glass of something that might have been a mixed drink but was probably Pepsi.
“Just nine months ago, Nate,” Hef was saying with his wide thin smile, eyes as bright as these of a ten- year-old who just got a train set for Christmas, “my baby didn’t exist.”
“Nine months is about right for a baby,” I said.
I was in my own After Six tux, and most of the men here were similarly dressed, though a few were in business suits. The look for both sexes was fairly formal, though in a surrealistic touch, dripping-wet couples in bathing suits and towels would come sloshing through at will, laughing, presumably heading somewhere to dry off.
Sitting on the arm of the sofa with her arm draped around Hef was a lovely blonde girl in her early twenties wearing a sort of obscene pink prom dress, her full bosom half out, white-blonde hair in a sprayed bulletproof bouffant. She had a very innocent face, and he was calling her Cynthia; she wasn’t calling him anything-we’d been sitting ten minutes and she hadn’t spoken. But her smile was swell, and her laugh created memorable jiggling.
The music was a little loud-a black combo Hef had recruited from the South Side, in sky-blue tuxes with black lapels and cuffs, was playing and singing “The Twist.” Not long ago, rock ’n’ roll was a subject of much derision here. But “The Twist” had changed that. Or anyway the way Hef’s female guests did the Twist had changed that.
“You know some people look at this,” Hef said, waving his pipe like a wand, “and all they see is sex.”
I was watching a dark-tanned, busty brunette in a blue bikini, her hair a beehive tower, do the Twist with a
