Askew, a 2005 graduate of the U.S. Military Academy at West Point, started his career as an armor officer with the 1st Armored Division and served two tours in Iraq. On December 18, 2011, he commanded the final serial, or convoy, of combat vehicles to leave Iraq. The convoy crossed the border with little military fanfare, but remarkable media coverage. Just moments after the last vehicle crossed the line, the border gates closed, ending U.S. Forces Iraq mission after nearly nine years.