Bootcheck played collegiately for the Auburn Tigers of the Southeastern Conference. He attended Michigan City (Rogers) High School for two years and Louisiana Porte High School for two years. He made his major league debut with the Anaheim Angels on September 9, 2003.
He has played in Major League Baseball, Nippon Professional Baseball, and the of Korea Baseball Organization. College Anaheim/Los Angeles Angels On May 2, 2006, Bootcheck was hurt while running from the bullpen to the mound during the Angels" brawl with the Oakland Athletics. He was placed on the disabled list with a hamstring injury and missed most of the season.
Pittsburgh Pirates He became a free agent after the 2008 season and signed a minor league contract with the Pittsburgh Pirates.
Yokohama Bay Stars In 2010, he played for the Yokohama Bay Stars of Nippon Professional Baseball. Tampa Bay Rays In 2011, he returned to Major League Baseball, signing a minor league contract with the Tampa Bay Rays.
On July 2, he was granted his release by Tampa Bay. He later played for the Lotte Giants in of Korea.
Detroit Tigers On December 11, 2011, he signed a minor league contract with the Detroit Tigers.
New York Yankees Bootcheck signed a minor league contract with the New York Yankees for the 2013 season. The Yankees called him up to the major leagues on June 14. He was designated for assignment on June 18, 2013.
Bootcheck opted to become a free agent, but re-signed with the Yankees shortly after.
The new contract includes an August 15 opt-out date. Philadelphia Phillies Bootcheck signed a minor league deal with the Philadelphia Phillies in December 2013.
He became a free agent after the 2014 season.
