Minor leagues (1984–1994) Kehoskie was hired as a
batboy by his hometown
Auburn Astros, then the short-season Class A affiliate of the
Houston Astros, in 1984 at age 11. From 1989 to 1991, he also covered the team as a correspondent for
The Citizen, Auburn's daily newspaper. In early 1992, Kehoskie was hired by the
Rochester Red Wings, then the
Triple-A affiliate of the
Baltimore Orioles, where he was a member of a staff that included
Joe Altobelli,
Russ Brandon,
Josh Lewin,
Bob Socci, and
Glenn Geffner. He worked for the Red Wings until late 1994.
Player agent (1996–2011) Kehoskie worked in the Minor Leagues for 11 years to become a
Major League Baseball general manager. After failing to land a job with an MLB team and wanting to remain in baseball in a job involving baseball operations and scouting, he started working as a player agent in 1996. One of his earliest clients was left-handed pitcher
Brad Pennington, who had pitched for the Rochester Red Wings when Kehoskie worked for the team. In 1998, Kehoskie was asked to represent a group of five
Cuban defectors in
Costa Rica, who became the first of approximately two dozen Cuban players he represented. Aside from Cuban defectors, Kehoskie has worked extensively in
Latin America, including the representation of players from the
Dominican Republic and
Venezuela. Among the notable players Kehoskie has advised or represented are
José Bautista and
Félix Hernández. == Media appearances ==