A star at the University of Tennessee, Chase Headley parlayed his run as a Volunteer to a Second Round Pick in the 2006 Amateur Draft.  Headley would make it briefly to the Majors (with San Diego) the following season.

Headley began 2007 in the Minors, but by June, he was back in San Diego and would become a starter before long.  Headley showed gradual improvement over the next four years, first playing in Leftfield but moving to Third Base, where he played most of his career.  In 2012, Headley would have the season of his life, posting career-bests in Home Runs (31), RBIs (115), and OPS (.875) while winning the Gold Glove, Silver Slugger, and the RBI Title.  Headley was also fifth in MVP voting, the only year he ever received a vote.

After slipping back to his regular production in 2013, Headley was traded mid-year in 2014 to the Yankees.  New York would send him back after the 2017 Season, and Headley played back in San Diego briefly before he was released in May.

With the Padres, Headley contributed 87 Home Runs, 879 Hits, and batted .263.