Chris Bootcheck's journey in professional baseball began when he was selected by the Anaheim Angels in the first round of the 2000 MLB Draft. A right-handed pitcher, Bootcheck made his Major League debut with the Angels on September 9, 2003. Over the next few years, he would spend time moving between the major league roster and the minors, honing his skills and gaining experience.

During his tenure with the Angels, Bootcheck primarily served as a relief pitcher. His time with the team saw him appear in various roles, including middle relief and spot starts. In 2007, he had his most active season with the Angels, appearing in 51 games and posting a 3-3 record with a 4.77 ERA. Despite showing promise, Bootcheck struggled with consistency, which led to fluctuations in his performance.

After his stint with the Angels, Bootcheck signed with the Tampa Bay Rays in 2009. However, his time with the Rays was brief, as he only appeared in three games before being designated for assignment. Following his release, Bootcheck continued to pursue opportunities in professional baseball, signing minor league contracts with several teams, including the Pittsburgh Pirates and New York Yankees.

Bootcheck's career also took him overseas, where he played in Japan for the Yokohama BayStars in 2010. This international experience provided him with a new perspective on the game and allowed him to continue competing at a high level. Upon returning to the United States, Bootcheck continued to play in the minor leagues, striving to make it back to the majors.

In 2013, Bootcheck achieved a brief return to the MLB with the New York Yankees. He was called up in June and made two appearances for the team. Although his time with the Yankees was short-lived, it marked a significant moment in his career, as he had successfully returned to the major leagues after several years.

Throughout his career, Bootcheck demonstrated perseverance and adaptability, navigating the challenges of professional baseball.