Herbert enlisted in the Army in Shelbyville, IN on 3 November 1943.

On 29 September 1944 Pvt Maddox was transferred to Service Company from Hq 82d Airborne Division as one of the replacement for losses suffered in the Holland Campaign. 

Pvt Maddox was subsequently transferred to Company A on 9 December 19044 and went into combat on 18 December 1944 in Belgium.  He was promoted to Pfc on 1 January 1945.

Exactly one month later he was wounded in action and evacuated to a field hospital.  He was placed on permanent assignment to that hospital's Department of Patients as of 31 May 1945.

It does not appear that he returned to the regiment although it is known that he re-enlisted on 12 June 1945.

Herbert's military decorations include the Purple Heart and the Combat Infantryman Badge awarded for action during the campaign, 18 Dec 1944 to 20 Feb 1945.