After his junior year of college, the San Diego Padres selected him in the 26th round of the 2008 Major League Baseball draft.[2] On June 15, 2008, Anna signed with his Padres and began his professional career with the AZL Padres. In 43 appearances between the AZL Padres and the Low-A Eugene Emeralds, Anna slashed .232/.341/.351 with 5 home runs and 24 RBI. The next year, Anna split the year between Eugene and the Single-A Fort Wayne TinCaps, posting a .280/.380/.440 slash line with 5 home runs and 31 RBI. In 2010, Anna returned to Fort Wayne and posted career-highs in both home runs (6) and RBI (32). He split the 2011 season between the High-A Lake Elsinore Storm and the Double-A San Antonio Missions, batting .277/.391/.419 with 5 home runs and a career-high 41 RBI. In 2012, Anna spent the season in San Antonio, hitting .271/.377/.393 in 129 contests. In 2013, Anna spent the season with the Triple-A Tucson Padres, slashing .331/.410/.482 with 9 home runs and 73 RBI.
On April 19, Anna pitched the eighth inning in a 16–1 loss to the Tampa Bay Rays, giving up two runs on three hits.[9] The next day, he drew a game-winning bases-loaded walk in the 12th inning against Rays' pitcher C. J. Riefenhauser.[10]
Anna was designated for assignment by the Yankees on July 3, 2014.[11]
Pittsburgh Pirates
Anna was claimed off waivers by the Pittsburgh Pirates on July 5, 2014,[12] and was assigned to the Triple-A Indianapolis Indians. He was designated for assignment on August 3 when Jayson Nix was signed by the Pirates.[13] He was outrighted to Triple-A Indianapolis and finished the year with a .235/.398/.338 slash line with the team.
St. Louis Cardinals
Anna signed a major league contract with the St. Louis Cardinals on November 11, 2014.[14] Anna spent most of the 2015 season with the Cardinals Triple-A affiliate, the Memphis Redbirds, but did appear in one at-bat for the Cardinals in an April 23 game against the Washington Nationals. In 125 games for Memphis, Anna slashed .272/.382/.355 with 3 home runs and 44 RBI. Anna returned to Memphis in 2016, slashing .266/.344/.341 with 2 home runs and 39 RBI in 106 games for the team. On September 4, 2016, Anna was designated for assignment by the Cardinals.[15] He was released by the organization on September 7.
Kansas City Royals
Anna signed a minor league contract with the Kansas City Royals organization on January 21, 2017. He was assigned to the Triple-A Omaha Storm Chasers, where he batted .285/.364/.376 with 5 home runs and 33 RBI in 114 games. He elected free agency on November 6, 2017.[16][17]
Philadelphia Phillies
On January 24, 2018, Anna signed a minor league contract with the Chicago White Sox organization.[18] On March 28, Anna was traded to the Philadelphia Phillies organization and was assigned to the Triple-A Lehigh Valley IronPigs.[19] In 122 games for Lehigh Valley, Anna posted a .271/.367/.341 slash line with one home run and 34 RBI. He elected free agency following the season on November 2.[20]
Minnesota Twins
On December 11, 2018, Anna signed a minor league contract with the Minnesota Twins organization.[21] On February 18, 2019, Anna announced his retirement from professional baseball.[22]