Coolbaugh attended Theodore Roosevelt High School and the University of Texas-Austin. In 1985 and 1986, he played collegiate summer baseball with the Chatham A's of the Cape Cod Baseball League and was named a league all-star both seasons. He was selected by the Texas Rangers in the third round of the 1987 MLB Draft.
Coolbaugh played for the Rangers in 1989 and 1990, for the San Diego Padres in 1991, and for the St. Louis Cardinals in 1994. He also played two seasons in Japan for the Hanshin Tigers in 1995 and 1996, and continued to play in the minor leagues until 1999.
In 1999, Coolbaugh played for the Triple-A Tucson Sidewinders and also was a player–coach for Double-A El Paso. In 2000, he was the manager of the High Desert Mavericks, and in 2001, he was the manager of the Lancaster JetHawks. In 2002, he was again the hitting coach for El Paso. Coolbaugh served as El Paso's manager from 2003–2004. From 2007–2008, he was the hitting coach for Double-A Frisco in the Rangers' organization. On December 29, 2008, he was named the hitting coach for the Triple-A Oklahoma City RedHawks. On June 8, 2011, the Texas Rangers brought him in from their Triple-A affiliate, Round Rock, to replace hitting coach Thad Bosley.

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