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Kup was far from conventionally handsome. He had a large nose and wore an obvious hairpiece. His garish wardrobe-wide lapels, gaudy plaids-made him look like “he had lost an election bet,” says Peggy Schatz. Yet she saw something “regal” about him. He was big but not flabby. He had football player shoulders and huge, powerful hands. He worked out regularly on an exercise bike. Steve Neal recalled Kup’s “swaggering presence, incredible vitality.”
“People pushed women at him all the time,” says one close friend. “Sometimes he succumbed.” In 1952 Joan Crawford asked Kup to join her at her home to watch the Oscars on television. She was up for a best actress award for Sudden Fear and did not want the cameras trained on her if she lost. Kup arrived to find the news crews camped on her lawn and Crawford in a gorgeous gown, her hair and makeup flawless. She didn’t win, and the crews quickly departed. “God damn it, come in my bedroom,” she barked at Kup, insisting in the most direct terms that he have sex with her. (The friend to whom Kup told this story says that Kup never revealed whether he had complied.)
Essee seemed proud that women were attracted to her husband-"Mae West really loved Irv,” Essee used to tell friends-and she seemed willing, to a point, to accept Kup’s girlfriends. She once confided to a friend that she had also strayed.
Essee raged, however, over what she suspected was an affair between Kup and a beautiful Chicago PR woman 20 years his junior, whose friendship he cherished to the end of his life. “That’s where the bitch lives,” Essee would hiss as she passed the woman’s apartment. The supposed lover denies that she ever “slept with Kup.” Not long before he died, Kup denied the affair, too, when his grandson, having heard the rumor so many times, asked if it were true.
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As Kup and Essee made their rounds, meeting friends and collecting items, he almost never paid their way-freeloading that would be barred by most major publications today. To the restaurateurs and club owners, however, a “Kup’s Column” mention of a new chef, a new show, or a celebrity sighting was worth a lot more than the food and drinks that Kup and his party consumed. Peggy Schatz says that neither Herb Lyon nor Kup ever paid at the Chez Paree. If the nightclub “could get that one little inch [of newsprint] advantage,” she says, “a $50 check, that was a cheap price.”
Kup certainly was not the only reporter accepting freebies in those days. Jeff Lyon recalls that his mother was strict about writing thank-you notes, mailing some 500 every holiday season to recognize the Scotch, bourbon, and fruitcakes sent to their apartment. “It’s not fair,” Lyon says, “to look at it through the lens of today.”
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Over the years, Kup expanded his roster of sources to include the underworld. He ran into “the boys” at clubs on Rush Street or at places like the Chez Paree. Kup treated them in his usual manner-a “Hi, buddy,” a slap on the back, and an expectation that they, like anyone else, would be a source of tips. And they were. Audri Adams, who handled publicity for the Pump Room, says Kup got items from Tony Accardo, Sam Giancana, and Gus Alex, all major Mob figures.
When Bugsy Siegel was shot to death in the Beverly Hills mansion of his girlfriend, Virginia Hill, in 1947, a True magazine reporter named Mike Stern called Kup. Hill had been hiding out, and Stern had heard she was living on money funneled to her by a local Mob bookkeeper. Stern guessed correctly that Kup might know him. Kup arranged a dinner at the Blackstone Hotel, and the bookkeeper mentioned in passing that Hill was staying in a small town in Montana. Stern found her and got his scoop. Why didn’t the mobsters retaliate against Kup? Stern, now 93, says they liked him. And by then he was too powerful to harm.
And he was very close to Sidney Korshak, the Los Angeles–based Mob lawyer, a childhood friend from the West Side. Korshak, who died in 1996, was an incomparable source of news for Kup, not only about Mob matters but also about Hollywood (he represented studios and studio heads) and labor (ditto unions and union bosses). In 1958, when the Sun-Times moved from its old building on Wacker Drive to its later home on Wa-bash Avenue and the river, Louis Spear faced a refusal by paper handlers to unload a shipment of newsprint that had arrived by water. Spear contacted Korshak, and with one telephone call, Korshak sent the paper handlers to work.
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