Kenneally began his athletic career at Boston Latin High School where he played varsity football, baseball, and held the city record for the fifty-yard dash.

Kenneally had many positions in the franchise; that of part owner, assistant Coach, team captain and offensive end.

In 1933, Kenneally left Boston with Lud Wray to play for and assist with the newly formed Philadelphia Eagles franchise.

Kenneally was offered the position of head coach and general manager of the Boston Shamrocks of the newly formed American Football League.

In 1939, Kenneally accepted the position of athletic director, head coach, and history teacher at Revere High School.

In 1950, he left the Revere athletic program in a vastly improved state and became the line coach at Brandeis University for four years.