Wrestling started for Jackie Kennedy in the eighth grade and it is also when his coach gave him the nickname “Pork Chop.” Later on, in high school, Kennedy invented a wrestling move that he called the “Pork Chop Roll” which he used throughout his career to pin opponents. He passed this move on over the years as he successfully coached high school grapplers.

Kennedy lettered in wrestling all four years Craddock High School, finishing third in the state tournament as a junior and going undefeated in dual meets as a senior. He also played football and was elected to the All-Tidewater, All- District and All-Foreman Field teams.

Wrestling, however, was his first love.

After high school, Kennedy attended prep school at Frederick Military Academy where he wrestled at heavyweight and was undefeated with a 20-0 record.

In 1964, Kennedy received a full scholarship to Virginia Tech for football and competed alongside his friend Ken Whitley on the football and wrestling teams. In his sophomore year, however, he broke his ankle and was unable to recover. Kennedy transferred to Elizabeth City State University where he played football and wrestled. Kennedy won the Central Intercollegiate Athletic Association three times, being named Outstanding Wrestler twice, and was also NAIA District 29 champion. In 1986, he was elected to the Elizabeth City State University's Hall of Fame.

In 1975, he was named head wrestling coach at Maury High School. Kennedy continues his support of Maury High School by providing scholarships for Maury athletes.

As a civilian, Kennedy coached the United States Navy World Wrestling team for four years and was selected athletic director for the U.S. Navy at Guantanamo Bay, Cuba in 1980. Kennedy was selected as the first civilian athletic director for the U.S. Marine Corps in Okinawa, Japan in 1984, and was selected Athletic Director of the Year for the U.S. Marine Corps worldwide in 1986.

Throughout his career, “Pork Chop” has had the support of his wife Margaret, his three children David, Jackie, and Leslie, and his eight grandchildren who have given him yet another nickname …”Big Daddy”.