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Capt. Riggle left active duty in the summer of 2000 and immediately joined the Marine Corps Reserves. In the fall of 2001 Capt. Riggle was in New York City. His reserve unit, MTU-17, stationed in Manhattan, were among the first military responders to the attacks on the World Trade Centers. Capt. Riggle was activated from Sept. 12th through the 30th, 2001, where he worked at ground zero moving rubble by hand in the bucket brigades. On November 10th (the Marine Corps birthday) Capt. Riggle received orders back to active duty for one year. He was assigned to Central Command (CENTCOM) in Tampa, Florida.
Riggle is a Lieutenant Colonel in the United States Marine Corps Reserve and served in Liberia, Kosovo, and Afghanistan. He is currently a public affairs officer with the New York City Public Affairs unit and is a recipient of the Combat Action Ribbon. He has referred to his military experiences on The Daily Show, often when acting as the show's "Military Analyst", sometimes stating he could kill any other member of the show. He is the only Daily Show cast member to have been in the U.S. military.
In August 2007, Riggle went to Iraq to report for The Daily Show as well as entertain the troops under the purview of the United Service Organizations.
On April 15, 2009, The Daily Show announced that Riggle had been promoted from Major to the rank of Lieutenant Colonel.