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“My mother lost the will to live after my sister died,” says Jerry. “She was a mess.” Within weeks of Karyn’s death, Howard Mendelsohn met Kup at Fritzel’s for lunch. Afterward, they parted to continue separately to their offices. When Mendelsohn turned to look back, he saw Kup in the middle of the Wabash Avenue Bridge, holding onto the railing and staring down at the water. “I know he was contemplating jumping,” he says.
Kup had his work to give structure to his days. Within a week or two of the funeral, he was broadcasting Bears games. Essee had nothing. She was drinking too much Jack Daniel’s, and she started taking pills. She flirted with converting to Catholicism for its belief in the afterlife, and she sent personal items of Karyn’s to psychics, hoping that they could help identify the murderer and also communicate with the dead young woman. “Irv was very attentive to her,” Stanley Paul recalls. “He was hurting, too, but he was just devoted to her.”
After a rough first year, Essee rallied. She focused on work that would keep Karyn’s memory alive and that would help high-school students find training and opportunities in the arts. Through the force of her personality, her contacts, and plugs in “Kup’s Column,” she raised the money to help found and support the private Chicago Academy for the Arts on West Chicago Avenue.
To those who didn’t know, Kup seemed not much different from before. He continued to be loyal to the Sun-Times, turning down offers from the Tribune. On Hedda Hopper’s death in 1966, the Tribune’s publisher, Don Maxwell, gave Kup the chance to move to Los Angeles, to take over her Tribune-syndicated column, as well as her house and office. “I don’t want to leave Chicago,” Kup told Mendelsohn. “Everything I love in the world is right here.” But the biggest reason was that Karyn had been murdered in Hollywood and, Kup wrote, both he and Essee thought the “memory was too fresh.”
Remarkably, though, Kup didn’t turn bitter. People noticed one subtle change: When he talked to old friends, he would never ask about their daughters.
But he was still capable of major acts of kindness. When Manny Skar, a Mob functionary and friend of Kup’s, was gunned down in 1965 near the garage of 3800 North Lake Shore Drive, newsmen converged on the luxury apartment building, tormenting the victim’s widow, Bea. In the next day’s column, Kup wrote a flattering description of Bea and distanced her from her husband, who had been indicted on charges of income-tax evasion. A couple of weeks later, Kup insisted that she accompany him to Fritzel’s. “A hush fell over the room as we walked in,” Bea recalls. As they moved toward their table, he whispered in her ear, “Walk and smile.” Waiting at the table was Kup’s lawyer. Both men, Bea says, “talked to the government [from a telephone] at the booth on my behalf.”
Kup and Essee wanted out of the Wellington Avenue apartment, with its memories of their daughter, and in the late 1960s they moved into The Carlyle, at 1040 North Lake Shore Drive, one of the first luxury condominiums to be built on the Drive. It was said that the developer, Kup’s friend Al Robin, gave Kup a steep discount because he would lend an air of celebrity to a venture that was somewhat risky. Jerry Kupcinet calls that charge “ridiculous.” The Kupcinets were original owners, and, Jerry says, they got the same deal as anyone else-four bedrooms, four and a half baths (about 3,100 square feet, including a terrace) for about $135,000. A recent search of Cook County records showed that no purchase price was recorded.
In the 1970s and 1980s, the ethics standards of journalists started to tighten, while Kup’s casual style remained largely the same. In 1980, Mayor Jane Byrne publicly called Kup and his counterpart at the Tribune, Bob Wiedrich, “two of the greatest freeloaders in the city.” A succession of Sun-Times editors grappled with the ethics nightmare that their popular columnist represented. Ralph Otwell, who was the editor from 1976 to 1984, tried gently to bring Kup up-to-date on changing standards. Among other things, he told Kup to curb the delivery to the Sun-Times of holiday “loot"-crates of gifts addressed to Kup that would sit on the loading dock for all to see. Kup “readily recognized that times had changed,” Otwell says. “He had the common sense to recognize that the paper came first.”
The embarrassments for the paper continued to erupt, however. In 1985, during the trial of Judge Richard LeFevour as part of Operation Greylord (an investigation of judicial corruption), a Cadillac dealer named Hanley Dawson Jr. testified that he had given free cars to Kup. Mike Royko, by then having left the Sun-Times for the Tribune, wrote that Dawson had given the Cadillacs “because he expected to receive favorable publicity in the column. Naturally, he wasn’t disappointed.”
By the 1980s, Kup was making about $300,000 a year from the column, and more from his work on TV and radio. His bosses at the paper knew they were getting a bargain. Kup and the advice columnist Ann Landers (who jumped to the Tribune in 1987) consistently topped readership polls, even outranking Mike Royko when they were all writing for the Sun-Times, says Ralph Otwell. Men especially bought the paper to read Kup, and, even in the 1990s, when both his heart and zest gave out, he still made the paper plenty of money. As always, his column ran toward the back, drawing readers-and thus advertisers-well into the paper.
Still, by the mid-1980s, there were undoubtedly many who read Kup more out of habit than in expectation of learning much. A new generation was coming into the media, and Kup began to look dated and even comic, with his cliché-laden items carrying updates on such aged stars as Bob Hope (“Ol’ Ski Nose") and featuring such press stoppers as who would “headline” this or that charity dinner and which local politician or grade-B actor was seen dining at which “eatery.”
In the WGN broadcast booth during Chicago Bears games, Kup sometimes dozed and had to be nudged awake before a commercial ended. “It was hilarious,” says his friend and Sun-Times colleague Ray Coffey. “[The announcers] couldn’t recognize the players.” PR man John Iltis recalls hearing about the time that Kup and Brickhouse were talking about a restaurant and they “missed a touchdown completely.” In 1976, the team’s general manager, Jim Finks, replaced both broadcasters.
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