Chase Headley, a third baseman known for his steady presence on the field, began his Major League Baseball career with the San Diego Padres. Drafted by the Padres in the second round of the 2005 MLB Draft, Headley quickly rose through the minor league ranks, making his MLB debut on June 15, 2007. His early years with the Padres were marked by a gradual development as he transitioned from the outfield to his more familiar position at third base.

In 2012, Headley had a breakout season that would define his career. He led the National League in RBIs with 115 and hit 31 home runs, earning him a Silver Slugger Award and a fifth-place finish in the National League MVP voting. That year, he also won a Gold Glove Award, highlighting his defensive prowess. This standout season showcased his ability to excel both offensively and defensively, solidifying his reputation as a reliable player.

Following his peak season, Headley continued to be a consistent performer for the Padres, although he never quite replicated his 2012 success. In July 2014, he was traded to the New York Yankees, where he provided stability at third base. His tenure with the Yankees was marked by solid defense and occasional offensive contributions. In 2015, Headley committed a career-high 23 errors, but he worked diligently to improve his defense, reducing his errors significantly in subsequent seasons.

Headley's time with the Yankees also saw him taking on a leadership role, often mentoring younger players. In 2016, he hit .253 with 14 home runs and 51 RBIs, contributing to the Yankees' efforts to remain competitive in the American League East. The following year, he batted .273 with 12 home runs and 61 RBIs, helping the Yankees reach the postseason.

In December 2017, Headley was traded back to the Padres, but his second stint with the team was short-lived. After struggling at the plate, he was designated for assignment in May 2018 and subsequently released. This marked the end of his professional playing career.

Throughout his time in MLB, Chase Headley was known for his work ethic and professionalism.