Gillespie was born in Portland, Oregon and raised in West Linn, Oregon, attending West Linn High School, the alma of former MLB pitcher Mitch Williams. For West Linn, Gillespie was a three-year letterman and won All-State honors as a shortstop and was also a standout pitcher. Gillespie also competed in football and basketball at West Linn, and later attended Oregon State University. After redshirting his freshman year at Oregon State, Gillespie won the Most Improved Player award his junior season and then later became a captain of the team. As a senior captain, Gillespie helped lead the Beavers to the 2006 Division I National Championship over the North Carolina Tarheels and was also named the Pacific-10 Conference Player of the Year.\n', '

Gillespie was drafted by the Milwaukee Brewers in the third round of the 2006 Major League Baseball Draft. After going pro in 2006, Gillespie played for their Rookie league Helena Brewers. He was promoted to the Class A-Advanced Brevard County Manatees in 2007. Gillespie spent the entire 2008 season with the Double-A Huntsville Stars. In 2009, he was promoted to the Triple-A Nashville Sounds.\n', '

In late July 2009, he was traded to the Arizona Diamondbacks with Roque Mercedes for Felipe López and assigned to Triple-A Reno. Following the season, he was added to the 40 man roster to protect him from the Rule 5 Draft, and made his major league debut in a pinch hitting opportunity on April 21, hitting a double and later scoring a run.\n', '

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