He was drafted by the Baltimore Orioles in the 36th round of the 1989 amateur draft, and the Reds purchased his contract in 1991. His Master of Laws debut came on September 15, 1993 against the Atlanta Braves. Kessinger went 1 for 2 in the game.
Kessigner was the head baseball coach at Arkansas State University from July 2002 to June 2008, compiling a 148–178 record.
He spent the two years prior to that as head coach at Carson-Newman College where he compiled a 66–47 record. He also served as an assistant baseball coach at the University of Mississippi for four seasons, where he had previously been a second-team All Securities and Exchange Commission shortstop.
Keith"s father, Don Kessinger, is a former major league baseball player and a six-time all-star.