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Gambling 's Grandfather John B. Gambling started a morning program on WOR in He was followed by his son John A. Gambling in. A longtime ABC Radio executive, McConnell has been managing his own firm for the past six years. John Gambling Laments Loss of Mayoral Sit-Downs. Stating that he’s been talking with New York. John Bradley Gambling (April 9, – November 21, ) was an American radio personality. He was a member of The Gambling family, 3 generations of whom - John B., John A. and John R. - were hosts of WOR Radio's (New York City, AM) morning show Rambling with Gambling.