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.
San Francisco Giants
On December 21, 2012, Gillespie signed a minor league contract with the San Francisco Giants. On July 5, 2013, the Giants purchased his contract and he joined the big league club.[4] After going hitless in 10 plate appearances, he was designated for assignment on July 9, 2013.
Chicago Cubs
On July 13, 2013, the Chicago Cubs claimed Gillespie off waivers. He was activated on July 14, and got a pinch hit single that night in the eighth inning against the St. Louis Cardinals. He was designated for assignment on September 4, 2013.
Seattle Mariners
Gillespie signed a minor league deal with the Seattle Mariners in December 2013. He was added to the 25 man roster, starting in left field for the Mariners on April 25, 2014. Going into a June 10 game against the New York Yankees, Gillespie was batting .327 with four multi-hit games, and batted in the cleanup spot for the first time in his major league career.[5] He was designated for assignment on July 4.
Toronto Blue Jays
On July 5, 2014, Gillespie was claimed off waivers from the Seattle Mariners by the Toronto Blue Jays. Kenny Wilson was designated for assignment to make room for Gillespie.[6] He made his debut with Toronto on July 6 against the Oakland Athletics. He was assigned outright to the Triple-A Buffalo Bisons on August 3. He elected free agency after the season ended.[7]
Miami Marlins
Gillespie signed a minor league contract with the Miami Marlins on December 6, 2014.[8]
He had his contract purchased by the Miami Marlins on June 27, 2015.
Pericos de Puebla
On February 27, 2017, Gillespie signed with the Pericos de Puebla of the Mexican League.[9] In 41 games he hit .296/.368/.401 with 2 home runs, 26 RBIs and 4 stolen bases.
Acerceros de Monclova
On May 20, 2017, he was traded to the Acereros de Monclova for first baseman Nate Freiman. He was released on June 4, 2017. In 10 games he hit .222/.282/.306 with 0 home runs, 3 RBIs and one stolen base.
Sugar Land Skeeters
On June 16, 2017, Gillespie signed with the Sugar Land Skeeters of the Atlantic League of Professional Baseball. He became a free agent after the 2017 season. In 47 games he hit .302/.385/.479 with 5 home runs, 26 RBIs and 12 stolen bases.
San Diego Padres
On February 28, 2018, Gillespie signed a minor-league contract with the San Diego Padres.[10] He was released on May 3, 2018.
