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From 1994 to 2002, Hollingshead was an assistant to R. C. Slocum at Texas A&M University, coaching tight ends and special teams. Prior to that, he served as head coach at famed Permian High School of Odessa, Texas, guiding the Panthers to a Class 5A State championship in 1991 and amassing a 43–4–2 record in four seasons. He had previously been an assistant coach at Permian, including the 1988 season covered in the book Friday Night Lights: A Town, a Team, and a Dream by H. G. Bissinger.
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