Ensberg was drafted in the 9th round of the 1998 Major League Baseball Draft. In spring training of, Ensberg and five of his teammates were in their hotel room when two gunmen burst in. Aaron Miles was in the next room and wrestled one of the gunmen to the ground before the other one fled, only to be caught later on. The other players involved were: Derrek Nicholson, Keith Ginter, Mike Rose, and Eric Cole. Ensberg enjoyed a stellar season, and was among the league leaders in home runs. He was also named Team MVP for the World Series Astros team. Ensberg was named to the National League All-Star team at the last minute in 2005, replacing the injured Scott Rolen. Ensberg had a career year in 2005, batting.283 while hitting 36 home runs and compiling a career high 101 RBI. Other than Barry Bonds, Ensberg was the only major league player to record at least 100 walks and have fewer hits than walks in 2006. On July 31, 2007, the Astros traded Ensberg to the San Diego Padres. This was only days after the Astros traded pitcherDan Wheeler to the Tampa Bay Rays for utility man Ty Wigginton. Houston paid the remainder of Ensberg's $4.35 million salary. Ensberg hit two home runs and a single in his Padres debut. Ensberg was not offered a new contract by the Padres and became a free agent on December 12, 2007. On January 31,, he signed a minor league contract with the New York Yankees with an invitation to spring training, anticipating to compete for the first base position. On March 22, Ensberg was added to the Yankees 40-man roster. In 2008, Ensberg hit.203 with a home run and 4 runs batted in for the Yankees. The Yankees designated him for assignment on June 1, and released him on June 8. On June 17, Ensberg signed a minor league contract with the Cleveland Indians. He became a free agent at the end of the season. On February 9,, Ensberg signed a minor league deal with the Tampa Bay Rays and was invited to the major league camp. However, he was released at the end of spring training. After the 2009 season, Ensberg decided to retire from baseball. Ensberg started a public blog and announced his intent to transition into a broadcasting career. Ensberg is the only MLB player in history to have won championship rings in college, rookie league, single A, AA, AAA, and to have played in a World Series.
Coaching career
For the 2011-2012 baseball season, Ensberg was hired as a hitters and infielders coach for the UC San Diego Tritons. Beginning in the 2013 season, Ensberg rejoined the Houston Astros organization as a developmental specialist at Class A Lancaster. The Astros announced his new role as a Minor League special assignment coach in 2014. On January 9, 2017, Ensberg was named manager of the Tri-City ValleyCats, Class A Short Season affiliate of the Astros in the New York–Penn League. On January 19, 2018, Ensberg became the manager of the Buies Creek Astros, Class A Advanced affiliate of the Astros in the Carolina League. Ensberg was named 2018 Best Managerial Prospect in the Carolina League by Baseball America. The Buies Creek Astros won the 2018 Carolina League with a record of 80-57. On January 18, 2019, Ensberg became the manager for the Tampa Bay Rays AA affiliate, the Montgomery Biscuits. Ensberg led the Biscuits to a club record 88-50. Ensberg was named 2019 Southern League Manager of the Year and also awarded 2019 Tampa Bay Rays Employee of the Year.