From 1998 to 2008, he was a sole practitioner, representing individuals and companies in litigation before both Federal and State courts.

From 2009 to 2015, he served as the Presiding Judge for the 61st Civil District Court of Texas.

From 2010 to 2011, he served as the administrative judge for the Harris County Civil District Courts.

[2][3] On September 18, 2014, President Barack Obama nominated Bennett to serve as a United States district judge of the United States District Court for the Southern District of Texas, to the seat vacated by Judge Kenneth M. Hoyt, who assumed senior status on March 2, 2013.

[4] On December 16, 2014, his nomination was returned to the President due to the sine die adjournment of the 113th Congress.