Moving On And Up
Caray went on to broadcast one season with the Oakland A's, but in 1971 began work with WFLD in Chicago as a broadcaster for the Chicago White Sox. He worked at Comiskey Park for eleven seasons. John M. McGuire of the St. Louis Post-Dispatch wrote, "Caray's firing was the best thing that could have happened to him. Because Chicago and Caray were made for each other." At one point during his tenure with the White Sox, the team's owner fired him because of his tendency to speak his mind on the air. When the White Sox were bought out months later, he was rehired. O'Neill stated, "Flaws in Caray's character are what made him so endearing."
Caray had made quite a name for himself in the broadcasting business. O'Neill explained, "For those who could not get to a game, listening was just as good, maybe better." O'Neill noted that throughout the years, "he became beloved as a symbol." Most people either loved him or hated him. He was one of a kind, and his broadcasts showed that style only he had. Not only that, but "he loved people from all walks of life," long time friend Otis Dunlap stated in an interview with McGuire. Dave Luecking with the St. Louis Post-Dispatch stated that "he considered all the fans his best friends." He never held back his disappointment with a player who made a bad move, nor held back praises when a home run was hit. In fact, he coined the phrases "It might be … it could be … it is! A homerun!" and "Holy Cow!" "Harry's passion for the game is so real. People identify with that," shared Bob Costas in an interview with Luecking.
Caray left the White Sox in 1982 to go across town to start broadcasting for the Chicago Cubs on WGN-TV. It was there he stayed until his death. In fact, according to Rod Beaton of USA Today, when asked when he was going to retire, Caray was quoted as saying, "I'll keep going until I die on the job someday." Caray endeared himself to the infamous Cubs fans immediately. One of the traditions was for him to sing "Take Me Out to the Ballgame" at the bottom of the 7th inning. That tradition started when he was singing in the broadcast booth one day and owner Bill Veeck got a kick out of his enthusiasm and turned on the PA system for everyone to hear.