Following a battalion command position in the
25th Infantry Division in Hawaii in the mid-1990s, Caldwell was sent to Haiti to work as political-military liaison in the U.S. Embassy during
Operation Uphold Democracy. After his tour in
Haiti, he commanded the 1st Brigade,
10th Mountain Division, at
Fort Drum, New York. He worked in the Office of the Director for Strategic Plans and Policy on the
Joint Chiefs of Staff at
the Pentagon, and later served as the executive assistant to the
Chairman of the Joint Chiefs of Staff. Caldwell was serving as deputy director for operations,
U.S. Pacific Command,
Hawaii, at the time of the 9/11 attacks, when the command's focus shifted from regional war plans to the Global War on Terrorism. In July 2002 Caldwell was assigned as senior military assistant to the deputy secretary of defense,
Paul Wolfowitz. In this position he served his boss during the preparation, execution, and follow on for the
Iraq War's
Operation Iraqi Freedom and other aspects of the Global War on Terrorism. From May 2004 until June 2006 Caldwell served as the Commanding General of the
82nd Airborne Division. As the division commander, Caldwell oversaw deployments by the units under his command to both Afghanistan and Iraq, as well as disaster-relief efforts following
Hurricane Katrina in New Orleans. Following his command of the 82nd, Caldwell was assigned as Deputy Chief of Staff for Strategic Effects and spokesperson for the
Multi-National Force – Iraq, a position he held for 13 months.
United States Army Combined Arms Center Caldwell was promoted to the rank of
lieutenant general in June 2007 and served as the Commanding General of the
Combined Arms Center at
Fort Leavenworth, Kansas. As the Commanding General for the Combined Arms Center, he has responsibility for the Command and General Staff College and 17 other schools, centers, and training programs throughout the United States.
NATO Training Mission-Afghanistan/Combined Security Transition Command-Afghanistan Caldwell assumed command of the
NATO Training Mission-Afghanistan (NTM-A)/Combined Security Transition Command-Afghanistan (CSTC-A) on November 21, 2009. Prior to the activation of NTM-A at that time, CSTC-A was a two-star command headed by then Major General Richard Formica. Elevating the Afghan training mission to a three-star command reflected the increased priority placed on training the
Afghan National Security Force (ANSF) as part of President
Barack Obama's Afghan "
Surge." Caldwell's efforts in Afghanistan received praise from figures in the military and government, including Senator
Carl Levin,
United States Secretary of Defense Robert Gates, and Admiral
Mike Mullen. During this assignment Caldwell was investigated after a subordinate claimed Caldwell directed him to use psychological operations in order to influence U.S. political leaders to support the military effort in Afghanistan. Doing so would be a violation of the
Smith–Mundt Act. However, an investigation cleared Caldwell of wrongdoing.
Dawood Military Hospital Three U.S. military officers testified that Caldwell tried to prevent the U.S. Department of Defense from investigating sub-standard conditions at an American-funded Afghan military hospital in Kabul. Caldwell's reasoning, according to Colonel Mark Fassl, was that there was "an election coming." However, Kenneth Moorefield, Deputy Inspector General for Special Plans and Operations, dismissed these allegations, claiming that there as no "attempt...to delay our investigation...or turn it off." The Department of Defense Office of Inspector General (DoDIG) conducted an investigation into the allegations and determined that Caldwell and his deputy Major General Gary S. Patton sought in 2011 to restrict contact with a team of investigators probing allegations of corruption and sub-standard patient care at Dawood National Military Hospital. The Inspector General recommended that the Secretary of the Army take appropriate action against Caldwell and his immediate subordinate, Major General Patton. An Army spokesman stated that, following the investigation, Caldwell "requested that he be retired, knowing that these substantiated allegations would directly prevent any future promotion or assignment to a position of importance and responsibility."
United States Army North (Fifth Army) Caldwell's final military command was
United States Army North, also known as the Fifth Army, which was also his father's final military assignment. Caldwell turned over command of U.S. Army North to Lieutenant General
Perry L. Wiggins on September 4, 2013.
Dates of rank ==Awards and decorations==