Prior to entering the police force he worked as a longshoreman, boxer, seaman, and was a secretary at U.S.

[8] When commissioner Francis W. H. Adams resigned to return to his law practice, he recommended Kennedy as his successor.

He opposed "curbstone justice" and instead instructed his officers to make arrests and have cases decided on by the courts.

[10] He was against the unionization of the NYPD and opposed the Police Benevolent Association of the City of New York's effort to become the force's official bargaining agent.

[11] In 1960, 2,000 officers petitioned the New York Supreme Court to arrest Kennedy after he defied an order to make promotions based on the civil service list.

He went all the way to the chief magistrate to see that the head of the PBA was fined for a parking violation and after a citizen's organization alleged police corruption in issuing cabaret permits, Kennedy had the group's leader investigated and unearthed a number of unpaid parking violations.

[10] In 1955, he refused to comply with Wagner's executive order granting a television crew headed by Theodore Granik access to the department's records, equipment, and manpower.

[12] In 1956 he was accused of being on "the verge of tyranny" by state assemblyman Anthony P. Savarese Jr. for refusing to turn over wiretapping data to a legislative committee.