Stewart was born the son of a retired Air Force lieutenant colonel and Vietnam War veteran, and, from a young age, he desired to follow in his father's footsteps.

[1][2] He graduated with a bachelor's degree in sociology and criminology from Auburn University, where he was also a member of the school's Air Force Reserve Officer Training Corps.

Following his retirement from the Air Force Reserve, Stewart moved to Charlotte, North Carolina.

He was appointed to the North Carolina Military Affairs Commission by Governor Pat McCrory in 2015.

[4] President Donald Trump tapped Stewart to be Assistant Secretary of Defense for Manpower and Reserve Affairs in January 2018 and was confirmed by the Senate on October 11.