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After landing a job as a sportswriter for the Chicago Times in 1935, Irv Kupcinet switched to “columning"-any noun risked becoming a verb in Kup-speak-in 1943. The Times’s managing editor and man about town, Russ Stewart, had recognized the qualities that the affable six-foot-one, 200-pound-plus former football player would bring to the assignment. (In 1948, The Chicago Sun and the Daily Times merged to become what eventually was named the Sun-Times, and Kup stuck with the tabloid until the end, refusing offers from the bigger, richer Tribune-loyalty being one of his many attractive qualities.)
His main competition, Nate Gross of the Chicago American, had grown lazy, collecting his items over the telephone, and for ten years Kup, aggressive and tenacious, had the run of the town. Then a new rivalry heated up when Herb Lyon, a former press agent, took over the Tribune’s “Tower Ticker” column. Lyon saw Kup as “not a very good writer, not a particularly deep thinker,” says Lyon’s son, Jeff, deputy editor of the Chicago Tribune Magazine. But Lyon respected his rival’s ability to “extract stories from people.” Like Kup, Lyon went out almost every night, always accompanied by his wife, Lyle. Jeff Lyon says the two columnists had a friendly competition, but there was nothing friendly about the competition between their wives. Richard Christiansen, the former chief critic for the Tribune, says that Lyle and Essee were “very conscious of status.” At the all-important Pump Room, the Kupcinets emerged on top. Booth One was always theirs.
In the mid-1960s, shortly after the Pump Room hired Stanley Paul to lead the nightclub’s orchestra, Irv and Essee invited him to join them on their nightly rounds of Chicago hot spots. Paul was in his mid-20s; the Kupcinets were some 30 years older. The three started the evening with dinner at one of Kup’s favorites, Fritzel’s, on State Street-"the Midwest equivalent of New York’s Toots Shor’s,” Kup declared-and then hit the Conrad Hilton, where the Kupcinets introduced Paul to Mayor Richard J. Daley and his wife, Eleanor (“Sis"). After that, the party decamped to the hotel’s Boulevard Room for an ice-skating show, before moving to the Empire Room in the Palmer House to see Jimmy Durante, followed by a stop at Mister Kelly’s on Rush Street to watch the comedian Totie Fields. At about 2:30 in the morning, the Kupcinets, with Paul in tow, landed at the Singapore, also on Rush, for Kup’s adored barbecued spareribs. “‘I’m falling asleep,’” Paul says he finally admitted to his hosts. “I said, ‘I have to go.’ They just looked at me, like, ‘Why?’”
The Sun-Times columnist Steve Neal, in an interview shortly before his death last February, said he came to know Kup in 1987 and even then he was still the king of his world. Kup walking into any restaurant in town, Neal recalled, “was like the parting of the Red Sea.”
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