High School and College
Headley graduated as valedictorian from Fountain-Fort Carson High School in Fountain, Colorado, in 2002. He distinguished himself in two sports, receiving four varsity letters in both baseball and basketball. In baseball, he was a three-time Colorado All-State player, and was named to the South Metro All-League team for all four of his seasons. Other high school honors included being named 2002 Player of the Year by the Colorado Springs Gazette, 2002 Male Scholar-Athlete of the Year by Rotary International/KRDO-TV, and 2002 Male Athlete of the Year by the Fellowship of Christian Athletes. He was selected to play in the 2002 Colorado Rockies Senior All-Star Game, in which he hit a home run in his first time at bat. He also played two seasons with the Colorado Rockies Select Scout Team, and in the National Baseball Congress World Series. In basketball, he was named to the All-Conference squad for two seasons.
Headley continued to play baseball in college, playing shortstop for the University of the Pacific in Stockton, California, and only transitioning to third base, which would become his primary position, when he transferred to the University of Tennessee in 2003. His sophomore year at Tennessee was difficult for him, as he had meniscus surgery on his knee, and a hamstring injury. He recovered, however, and worked out 62 walks (breaking Todd Helton's 1995 school record), approached the college's single-season mark for on base percentage, and was named the 2004 team Most Valuable Player. He also did not neglect his studies, becoming an Academic All-American with a 3.63 GPA, majoring in Sports Management. He was drafted by the San Diego Padres in the second round of the First-Year Player Draft in June 2005.
Headley was a high school class valedictorian and academic All-American.
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