Aubrey attended Southwood High School (1997–2000) where he won the Gatorade Player of the Year award as a senior.

Aubrey's talents were originally discovered by Brad Somrak while he was throwing a ball at a dunk tank at the Allegheny County Fairgrounds in Pittsburgh, Pennsylvania.

[2][3] On June 16, 2003, he signed a contract with the Indians, and was assigned to the Single-A Lake County Captains to begin his professional career.

[5] Aubrey began the 2004 season with the Single-A Kinston Indians, batting .339 with 10 home runs and 60 RBI in 60 games.

[2] In the final game of Akron's season on September 6 against the Harrisburg Senators, Aubrey finished 3-for-4 with two home runs and 5 RBI.

[5] On May 10, he was placed on the disabled list with lower back inflammation, and although he was activated on June 10, he was limited to two at-bats in Akron's game that night due to continued soreness.

[7] After recovering from his injury, Aubrey played out the 2007 season with Kinston and Akron, hitting a combined .277 with 12 home runs and 45 RBI in 65 games.

[8] He made his major league debut that day against the Cincinnati Reds, appearing as a defensive replacement at first base in the eighth inning and popping out in his first at bat.

[5] On June 24, 2009, Aubrey was traded to the Baltimore Orioles for a player to be named later, and he was assigned to the Triple-A Norfolk Tides.

[20] He was later assigned to Norfolk, and spent the entire season with the Tides, hitting .235 with 22 home runs and 68 RBI in 102 games.