Born in Columbia, South Carolina, Kennedy graduated with a Bachelor of Arts from the Princeton School of Public and International Affairs (then the Woodrow Wilson School of Public and International Affairs) in 1970 after completing a senior thesis titled "Black Politics in Indiana, 1888-1900.

Following graduation, he worked for the law firm of Reavis, Pogue, Neal and Rose in Washington, D.C.

Subsequent to this he was an Assistant United States Attorney for the District of Columbia between 1973 and 1976.

He was appointed Associate Judge of the Superior Court of the District of Columbia in December 1979 where he served until he was appointed as a federal judge in September 1997.

On May 15, 1997, Kennedy was nominated by President Bill Clinton to a seat on the United States District Court for the District of Columbia vacated by Joyce Hens Green.