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 fiftyish guy in glasses eyeing her the way a dog does a squirrel. He was some kind of associate editor at the magazine.
“How did they get that idea?” I asked.
He ignored my sarcasm, or maybe didn’t pick up on it over the loud music. There was considerable chatter, as well—we were near the endless buffet table. Food smells were pleasant. Bunnies were circulating taking drink orders.
I said, “I had a few people over the other night myself. Would have called you but I’m particular.”
“You don’t think I know I’m the luckiest human being in the world?” He painted the air with his pipe smoke. “But I’m also doing the world, this modern world, a favor—people who work hard should get to play hard. You get one time around this merry-go-round, and if you don’t make the most of it, who do you have to blame?”
“Now you’re a philosopher.”
“This is a new decade, Nate. Pretty soon we’re going to have a new president.” He grinned, and his eyes danced with manic delight. “I think we know who that’s going to be.”
“Nixon’s ahead in the polls.”
“Tricky Dick won’t win. What Playboy represented in the fifties was my personal dream—sexual pleasure, material abundance, without guilt. But now it’s time to break down other barriers—take civil rights, for example…”
Shrill, giddy laughter and applause rode over Hef’s speech, and “The Twist” ground to a halt. Tonight’s guests of honor had arrived, fresh from the Near North Side’s Chez Paree—Frank Sinatra, Dean Martin, and Sammy Davis, Jr. (Joey Bishop and Peter Lawford weren’t on the Chez bill), moving past the suits of armor down into the living room, stopping to talk to men they knew and girls they wanted to know. Somebody was doing the fingers-in-the-teeth whistle: Hef’s bouncy blonde.
Everybody crowded around a little performance area adjacent to a piano, bass, and drums, where a trio of musicians awaited, and without preamble, the Su
mmit (they didn’t call themselves the Rat Pack) went into an abbreviated version of its Vegas show.
First Dean went out to sing while the other two faded back to a nearby liquor cart. After drunkenly asking what all these people were doing in his room, the big well-tanned handsome crooner, in a tux with loose crossover tie, did a lighthearted “Volare,” then several song parodies (“You made me love you … you woke me up to do it”). He was delivering a straight “June in January” when Davis, sans tux jacket, strode over, mimicking Martin’s ex-partner Jerry Lewis (“Deeeeeeean!”) and Dino responded accordingly (“Jer—you’ve changed! But at least you’re still Jewish.…”). The two walked off arm in arm and Sinatra took their place.
It was always a surprise how small Frank was, and even more surprising how quickly you forgot that when he sang. His tux tie was still snugged in place, but he was loose as he did a jazzy “Chicago,” getting the expected wild response, then “Luck Be a Lady,” which played surprisingly well without a big band.
Then Dean carried Sammy out in his arms and presented him to Sinatra as a token of appreciation from the NAACP, and this got howls, particularly from Sammy.
The little Negro—and he made a giant out of Sinatra—was probably the most talented of them, and he sang a very earnest “Hey There” (a hit of his) and then “Birth of the Blues,” doing some flashy dancing. Finally he went into “The Lady Is a Tramp” and had lapsed into a Sinatra impression when the other two came out and shut him down.
The three together did a bunch of comedy that had most everybody in stitches, but I have to admit I would rather they’d kept singing. Maybe it was because I’d seen this act—with Bishop and Peter Lawford mixed in—three times, and knew all the “improvisation” was written.
And a lot of it played on Sammy being colored. Racial stuff that was so stupid, they were spoofing it, so hip and cool they could get away with it. Sammy laughed hard, bending over and slapping his thighs, at Frank and Dino’s darkie stuff (mostly Amos ’n’ Andy references), but I always noticed you didn’t actually hear Sammy laughing.…
They were doing a “Guys and Dolls” medley when somebody came pushing through the crowd—it was Peter Lawford, also in a tux.
“Fellas!” he said. “How could you start without me?”
Sammy said innocently, “We were gonna wait, Pete, but nobody could remember what it is you do.”
This got a big laugh, then Sinatra and Martin mugged while Lawford and Davis did a little soft-shoe bit—the expatriate Britisher had after all been a star in musicals at MGM—and finally Lawford held his hands up to the crowd.
“The real reason I waited to come on this late,” he said, with that barely there British accent, “was so I could introduce a new member to our little Summit.”
Sammy said, “Bobby Darin?”
Sinatra raised a fist and gave him a comic glare.
“No, no,” Lawford said, with that nice big winning smile of his. “Ladies and gentlemen, the next president of the United States—and I don’t mean Hugh Hefner.…”
Gasps blossomed everywhere as all eyes went to the presidential candidate gliding effortlessly through the crowd in a brown suit with a red tie, straight from some political event, tanned and handsome, his brown bangs slightly tousled. Everyone knew he was in town, campaigning for this crucial state, but his presence here was a surprise.
By the time he reached the little performing area, the applause was ringing in the big old remodeled ballroom. It was dying down when Kennedy said to the pianist, who was doing a jazzy “Hail to the Chief,” “I, uh, want to thank you for your positive outlook.”
When he finally spoke, in that distinctive halting Massachusetts way of his, he was casual and gracious. “I didn’t come around, uh, to spoil the party with a campaign speech. I just want to thank my friend Frank, for, uh, the great work he’s doing. You’ve heard his jingle?”
Laughter and clapping and a few whoops indicated they had—a specialty version of “High Hopes” that was running in radio and TV ads.
With a smile, the candidate turned to Sinatra and said, “You know, uh, Frank I think you may have a future in this recording business.”
Sinatra made a dismissive gesture, but he was beaming.
“And, uh, I have to thank our host, Hugh Hefner. He represents a breath of, uh, fresh air in our rather stale culture … but don’t quote me. Jackie doesn’t approve of the centerfolds.”
As laughter rang, front-row Hef grinned and shrugged, pipe in hand.
“And, uh, Hef … if I may, without embarrassing you … I’d like to thank you for your, uh, generous financial contributions. And all of you very, uh, prosperous-looking individuals, I know my campaign would be grateful for, uh, any help you might still give. We’re coming down to the wire now. And don’t miss the first of, uh, three televised debates, coming soon to a living room near you. Should be exciting. I understand, if things don’t go well for him, Dick Nixon may be, uh, reprising his famous Checkers speech.”
That got a huge laugh. He gave a little wave, and Sinatra and company sang the “High Hopes” rewrite as the presidential hopeful mingled. This was the kind of hip group that gave even the likes of JFK some space. I didn’t see a soul ask for an autograph, and soon he’d disappeared.
I spotted him with Lawford in the sunken bar, where the window on the swimming pool glowed hypnotically with subdued lighting and unsubdued female flesh. A lot of smoke swirled in here, and Lawford had lighted up, but not Kennedy.
The candidate was nestled in a booth, and I knew he had a terribly bad back—sometimes wore a brace—so I motioned for him not to get up, offering my hand to shake, which he did, flashing that famous smile.
“My favorite private eye,” he said. “Is it, uh, true James Bond was based on you?”
“No, it’s just the tux,” I said, and nodded to Lawford, exchanging smiles. “But I would like to get some of his action.”
Kennedy grinned. “Who wouldn’t?”
Absently, flicking ash into a tray, Lawford said, “You know, they offered me that part. Money was poor, and I turned it down. They’re going with an unknown.”
“Too bad for them,” Kennedy said. “Uh, Peter—could I have a word with Mr. Heller?”
“Most certainly,” the actor said good-naturedly, sighing smoke, then sliding out of the booth.
I took his place. A Bunny came over, but Kennedy already had a mixed drink of some kind going; me, too—a vodka gimlet.
“You know, Nate, I, uh, always look forward to seeing you.”
“Why’s that?” I didn’t figure we’d ever exchanged more than a dozen sentences.
“You’re not a bore,” he said, and twitched half a smile. “And you’re not a yes-man. I have so many of those.”
“That’s because you like it that way.”
Which made him laugh. “See? Exactly what I mean. You know, Bobby, uh, thinks the world of you.”
“I like him back. He’s a bulldog. Reminds me of a friend of mine.”
“Oh? Who’s that?”
“Late friend of mine. Eliot Ness.”
“On TV?”
“No, the real man. He was shorter than Robert Stack, but a better actor.”
Kennedy grunted a little laugh. “Funny to think of somebody like that—so much larger than life? Actually existing. Walking around. Just a man, like the rest of us.”
Like the rest of us.
“What can I do for you, Jack?” I felt I could take the first-name liberty—I mean, he wasn’t president yet; and anyway, I was the guy who made his first marriage go away. And I wasn’t even pope.
“You, uh, know how stubborn Bobby is about his, uh, his passion.”
“I’m not sure.” I should have known what he meant, but in my defense, half-naked Playmates nearby were bobbing up and down underwater.
“The, uh, issue you worked with him on, years ago.”
“Organized crime. Teamster corruption. I wouldn’t call it an issue. But your brothe
r’s passionate about it, all right.”
He sipped his drink; his eyes no longer met mine. “Bobby doesn’t always, uh, understand the waters we must swim in.”
Again, in this context, that could be taken wrong. Wasn’t that Miss January?
“What are you saying, Jack?”
Now his gaze rose. If his voice had been any softer, the piped-in jazz would have covered it. “I may need, uh, from time to time, the, uh, help of an intermediary … a liaison … with certain types of individuals.”
“Mobsters, you mean. Isn’t that what Sinatra is for?”
Kennedy’s smile was faint. “Frank’s a good friend, but he, uh … he’s a public figure, and he has a temper, and can be … controversial.”
As in, everybody from Hoboken to Hollywood knew Sinatra had mob ties. That hadn’t stopped the Kennedys from using Frank’s fame to their benefit in this campaign.
I said, “You’re saying you may need to get the occasional message to guys like Johnny Rosselli or Sam Giancana, and may need someone reliable to handle that.”
“Yes. But, uh, Nate, let’s not use specific names.”
I had a sip of gimlet. “If you win this thing, you’ll have the Secret Service, and the FBI, and—”
He held up a hand. “The Secret Service needs, I think, to steer clear of such matters, if possible. And the FBI, uh, well—you’ve had your own run-ins with J. Edgar Hoover, I, uh, understand.”
“Yeah. Told him to go fuck himself, back in ’34. Before that kind of thing was fashionable.”
He liked that.
“Jack, I’m glad to help, but if I could put in my two cents…?”
“Throw in as much as you like, Nate. The, uh, campaign coffers can use it.”
“I hear you got some help in West Virginia.”
The story was that Giancana had pulled strings in that state and pumped in money, some of it from a Teamster pension fund. That made Jack beholden to both Giancana and Hoffa, two of his brother’s least favorite people.
“It was a, uh, tough primary.”
“Not as tough as the general election’ll be. And if it’s Illinois that puts you over the top? And Giancana is, or even just thinks he’s the one who made it happen? Well … those are dangerous waters, Jack.”
Bye Bye, Baby Page 5