After his junior year of college, the San Diego Padres selected him in the 26th round of the 2008 Major League Baseball draft.

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.

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.

[3][4][5] In spring training in 2014, Anna competed with Eduardo Núñez, Zelous Wheeler, Yangervis Solarte, and Scott Sizemore for a reserve infielder role with the Yankees.

[7] Anna hit his first career home run on April 10, against Boston Red Sox pitcher Clay Buchholz.

[8] 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.

Anna signed a minor league contract with the Kansas City Royals organization on January 21, 2017.

[18] On March 28, Anna was traded to the Philadelphia Phillies organization and was assigned to the Triple-A Lehigh Valley IronPigs.