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Though he wrote a gossip column, Kup thought of himself as a reporter first, and Dennis A. Britton, who became the editor of the Sun-Times in 1989, argues that Kup “had journalism skills as good as anyone I ever saw.” Kup had sources everywhere. In government, for instance, his weekly call list included the political heavyweights George Dunne, Neil Hartigan, Dan Rostenkowski, and Henry Hyde. (Kup was a Democrat-he loved Harry Truman and Hubert Humphrey most of all-but he had many friends besides Hyde in the GOP, including President Gerald Ford, a teammate on the 1935 college all-star football squad.) Britton says that Kup had “a corps of tipsters from federal judges to cops on the street. He called 30 to 40 people each week.”
And he got breaking news. He was the first to report President Harry Truman’s decision not to run in 1952-confided by the President himself. Around 1960, he broke the story that his friend Sammy Davis Jr. was about to present an engagement ring to Kim Novak. (The head of Novak’s movie studio decided marriage to a black man would decimate her at the box office, and he ordered Mafia thugs to warn off Davis. The romance ended.) When Britain’s Princess Margaret visited Chicago in 1979, Kup was the first to report her slur (“All Irish are pigs!") in a conversation with the city’s most prominent Irishwoman, Mayor Jane Byrne.
In the 1990s, even as Kup was fading, he continued to break stories. In 1993, Steve Neal was with him at Comiskey Park when Kup excused himself to talk to a young woman, whom Neal did not recognize. Kup got the scoop that Michael Jordan was retiring (for the first time). The woman was Juanita Jordan.
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Being plugged in helped Kup move into television in its infancy. He started in the early 1950s with a WGN-TV variety show, followed by a late-night news and interview show on WBBM, which lasted until 1957, when Kup became the Chicago anchor for NBC’s “America After Dark,” a precursor of “The Tonight Show Starring Johnny Carson.” In 1959 came “At Random” on WBBM, a talk show that started at midnight and continued until the host and the guests-some of whom wandered by after their nightclub acts-ran out of things to say, usually around three in the morning. “At Random” later became a more conventional, hourlong show on Channel 5, then 7, and, finally, 11. Guests over the years included Richard Nixon, Malcolm X, Muhammad Ali, Milton Friedman, Martin Luther King Jr., Jimmy Hoffa, Judy Garland, and University of Chicago president Robert Maynard Hutchins. What made the show work was Kup himself, says Todd Whitman, his producer in later years: “[His ability to] put together people from different walks of life . . . I don’t think anyone has done it like Kup. He sat back and let everybody else intermingle, didn’t hog the spotlight-common guy sitting and observing.”
Starting in 1953, Kup teamed with the veteran announcer Jack Brickhouse to provide color commentary on radio broadcasts of the Bears games. The job fit seamlessly with his column. One Sunday when Kup was new to the show, Brickhouse asked Kup if he needed help lining up guests for halftime. Kup said he thought he would be OK, and just before halftime Harry Truman, Bob Hope, and the middleweight boxing champ Carmen Basilio walked into the booth.
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