As of July 2018, he was serving as deputy director of the United States Army National Guard.

[3][4] Whittington later received a master of strategic studies degree from the United States Army War College.

During Operation Desert Storm, he served in Kuwait and Iraq as a battery executive officer.

Since joining the Maryland National Guard in 1993, he has commanded and held staff assignments at the battery, battalion and brigade levels.

In March 2007, Whittington deployed to Camp Victory, Iraq as deputy commander, 58th Infantry Brigade Combat Team.