General Caldwell has served as the President of Georgia Military College since November 1, 2013, during which time several new campuses were opened, growing the GMC footprint in Georgia to include the Main Campus in Milledgeville, 11 community college campuses, and the Global Online Leadership College.
Georgia Military College Preparatory School (K-12 grades) has also experienced growth under General Caldwell's leadership, having added third grade in 2019, and grades K-2 in 2021. With the addition of the elementary grades, GMC Prep School also expanded its campus footprint with the historic preservation and restoration of Jenkins Hall, and now Wilder Hall, and new construction of the Prep School Annex. These buildings now house grades K- 5 in the Prep School.[8]
Military career
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.
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.[9]
Caldwell walks in Eastern Baghdad in April 2007.
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
New York City policemen are greeted by Caldwell as he visits the Times Square Military Recruiting Station on March 10, 2008.
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'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.[12][13]
^Abi-Habib, Maria. (2011). "Neglect at Afghan Military Hospital, Graft and Deadly Neglect" from Abi-Habib, Maria (3 September 2011). "Neglect at Afghan Military Hospital". Wall Street Journal. Archived from the original on 2015-02-08. Retrieved 2015-02-08.
^Abi-Habib, Maria. (2012) Pentagon Is Pressed on Afghan Inquiry from Abi-Habib, Maria (18 June 2012). "Pentagon is Pressed on Afghan Inquiry". Wall Street Journal. Archived from the original on 2015-02-08. Retrieved 2015-02-08.
^Congressional Testimony. (2011). Defense Authorization Request for Fiscal Year 2012 and the Future Years Defense Program. Retrieved February 19, 2011, from "Untitled Document". Archived from the original on 2011-03-04. Retrieved 2011-02-20.
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