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Choosing to attend the United States Military Academy at West Point, he captained and played quarterback on Army's football team in the 1984 season, in which he helped the team achieve one of its best recent records, exceeding all expectations with an 8-3-1 record. In a heralded victory in the annual Army-Navy Game, Sassaman ran for 154 yards and two touchdowns, and later led Army to a rare post-season appearance with a win over Michigan State in the Cherry Bowl, and reportedly, for much of that 1984 season, Sassaman played with three cracked ribs.
Colonel Sassaman was awarded a Bronze Star Medal with 'V' for VALOR device, which he earned for his actions when his patrol came under attack in August 2003.
In this engagement, Colonel Sassaman dragged one of his wounded soldiers from his vehicle under heavy machine-gun and R.P.G. fire, after which he then chased down the Iraqi insurgents and killed them. At that time, aged 40, Sassaman was considered to be "the most impressive American field commander in Iraq." 
An incident in which some of his troops forced two Iraqi civilian detainees to jump into the Tigris River, one of whom allegedly drowned, led to a reprimand which then effectively ended his military career and he retired in 2005.
Colonel Sassaman is a recipient of the Bronze Star Medal with 'V' for VALOR device; the Defense Meritorious Service Medal; the Meritorious Service Medal with 2 Oak Leaf Clusters; the Joint Service Commendation Medal; the Army Commendation Medal with 2 Oak Leaf Clusters; the Army Achievement Medal with Oak Leaf Cluster and is entitled to wear the Combat Infantryman Badge, the Ranger tab and Army Parachutist Wings.
He currently consults nationally to corporations, public agencies and small businesses.