Gambling's Grandfather John B. Gambling started a morning program on WOR in 1925. He was followed by his son John A. Gambling in 1959. He brought his son John R. Gambling to the microphone in 1985 as co-host, and then the solo host starting in 1991. WABC then brought Gambling over in 2000, and he returned to WOR in 2008, where he eventually retired in December of 2013. That retirement ended up being short lived.