The Kennedy name has always been both popular and synonymous with Boston and vicinity. Thus, the WRKO powers-that-be selected that powerful name for Tom (his real first name is Tom). Tom had a voice and charismatic personality to match the Kennedy name, and the aircheck (available below) was made during one of his first days at The Big 68.

Kennedy began his Radio career while in high school in Michigan, and finally arrived at WRKO in May of 1970 from WNHC/New Haven, Connecticut, also a Drake-type Top-40 station at the time. In August of 1972, facing WRKO's format switch to a hybrid AOR, Tom moved on to KFRC in San Francisco. Kennedy would eventually return to Boston and work at both WHDH and WBZ radio.

Today, Tom owns and operates The Kennedy Group, a successful coaching and public-relation agency.