Drafted by the Chicago White Sox in the 9th round of the 2007 MLB Draft from DeSoto High School (TX). Started his pro career in 2007 with the Bristol White Sox of the Appalachian League, appearing in 26 games and hitting .203 with seven RBIs in 74 at bats. In 2008, he spent the entire year with Bristol, playing in 43 games and hitting .272 with four homers, 31 RBIs and 11 doubles. Struck out 43 times compared to just six walks. In 2009, Gilbert started the year with the Great Falls Voyagers of the Pioneer League and played in 12 games, hitting .277 with three RBIs. The White Sox released him in July of 2009 and he signed with the Evansville Otters. He played 25 games with Evansville, hitting .277 with eight RBIs and five doubles in 101 at bats.
In 2010, he signed with the Laredo Broncos of United League Baseball and appeared in 55 games. Gilbert hit .363 with the Broncos, tallying four homers and 55 RBIs with 16 doubles in 212 at bats. His stellar 2010 season earned him a contract with the White Sox and he was sent to single-A Kannapolis in 2011. With the Intimidators, Gilbert hit .257 with one homer and 26 rBIs and eight doubles in 183 at bats and 56 games. In 2012, Gilbert signed with the Fort Worth Cats of the North American League, playing in July and August and appearing in 27 games, hitting .212 with 11 RBIs and two doubles.