Caray was born Harry Christopher Carabina to an Italian father and Romanian mother in St. Louis. He was an infant when his father died. His mother remarried with a French-American, but after her death when Caray was eight, he went to live with his aunt Doxie at 1909 LaSalle Street in a tough, working-class section of St. Louis. As a young man, Caray played baseball at the semi-pro level for a short time before auditioning for a radio job at the age of 19.

Caray caught his break when he landed the job with the Cardinals in 1945 and, according to several histories of the franchise, proved as expert at selling the sponsor's beer as he'd been in selling the Cardinals on KMOX. Immediately preceding the Cardinal job, Caray announced hockey games for the St. Louis Flyers. Caray co-announced with Ralph Bouncer Taylor, former NHL player. On one occasion Taylor temporarily ended his retirement when he volunteered to play goalie for the Flyers in a regular season game with the team from Minnesota. (Caray and broadcast partner Gabby Street also called games for the St. Louis Browns in 1945-1946.) Caray was also seen as influential enough that he could affect team personnel moves; Cardinals historian Peter Golenbock (in The Spirit of St. Louis: A History of the St. Louis Cardinals and Browns) has suggested Caray may have had a partial hand in the maneuvering that led to the exit of general manager Bing Devine, the man who had assembled the team that won the 1964 World Series, and of field manager Johnny Keane, whose rumored successor, Leo Durocher (the succession didn't pan out), was believed to have been supported by Caray for the job. Caray, however, stated in his autobiography that he liked Johnny Keane as a manager, and did not want to be involved in Keane's dismissal. As the Cardinals' announcer, Caray broadcast three World Series (1964, 1967, and 1968) on NBC. In November 1968, Caray was nearly killed after being struck by an automobile while crossing a street in St. Louis; he suffered two broken legs in the accident, but recuperated in time to return to the broadcast booth for the start of the 1969 season. Cardinals' president Gussie Busch, then CEO of owner Anheuser-Busch, spent lavishly to ensure Caray recovered, flying him on the company's planes to a company facility in Florida to rehabilitate and recuperate. On Opening Day, fans cheered when he dramatically threw aside the two canes he had been using to cross the field and continued to the broadcast booth under his own power. Following the 1969 season, the Cardinals declined to renew Caray's contract after he had called their games for 25 years, his longest tenure with any sports team. The team stated that the action had been taken on the recommendation of Anheuser-Busch's marketing department, but did not give specifics. At a news conference afterward, where he drank conspicuously from a can of Schlitz, at that time a major competitor to Anheuser-Busch, Caray dismissed that claim, saying no one was better at selling beer than he had been. Instead, he suggested, he had been the victim of rumors that he had had an affair with Gussie Busch's daughter-in-law.

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