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.

[24] 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.

Aside from Cuban defectors, Kehoskie has worked extensively in Latin America, including the representation of players from the Dominican Republic and Venezuela.

Since the late 1990s, Kehoskie has been quoted frequently in the media on baseball-related topics, including Cuban defectors,[11][14][27] baseball in Cuba,[28][29][30] and the use of PEDs in Latin America.

[26] In 2008, Kehoskie told author Michael Lewis, "There’s at least half a billion dollars of baseball players in Cuba right now and probably a lot more.

[36][37] After signing with the Cincinnati Reds for over $30 million, Chapman was moved to the bullpen before he had started a single game in the major leagues.