Col. Derek Oakley is commander of the 28th Bomb Wing, Ellsworth Air Force Base, South Dakota, the largest B-1 combat wing in the United States Air Force, with more than 12,000 active-duty military, civilian employees, and family members. He provides combat-ready aircraft, crews and associated combat support for global engagement taskings.
Col. Oakley received his commission from the United States Air Force Officer Training School in May 2000. He graduated from pilot training at Columbus AFB, Mississippi, and was operationally assigned to the B-1B.
He has served in a variety of flying squadrons as an instructor and evaluator pilot in the B-1B, T-6, and T-38. He commanded a T-6 squadron at Columbus AFB and served on the Joint Staff as the Director of the Joint Targeting School, Dam Neck Naval Air Station, Virginia.
He served as the director of the B-21 Integration and System Management Office where he liaised between Air Force Global Strike Command and the Department of the Air Force Rapid Capabilities Office, supporting development of the B-21 Raider, the Air Force’s Top 3 priority acquisition program.
Prior to his current assignment, Col. Oakley commanded the 28th Operations Group at Ellsworth, the largest operational B-1B group in the U.S. Air Force with one operations support squadron, two bomb squadrons and management of the Powder River Training Complex.
Col. Oakley is a command pilot with over 3,400 flight hours in the B-1B, T-38, T-6, and T-37, including 991 combat hours in support of Operation Enduring Freedom.
EDUCATION
1996 Bachelor of Arts, Secondary Education, Judson College, Elgin, Ill.
2006 Squadron Officer School, Maxwell Air Force Base, Ala.
2007 Masters of Arts, Management, American Military University, Charles Town, W.Va.
2009 Air Command and Staff College, Maxwell AFB, Ala., by correspondence
2013 U.S. Army Command and General Staff College, Fort Leavenworth, Kan.
2014 Joint and Combined Warfighting School (JPME Phase II), Joint Forces Staff College, Norfolk, Va.
2019 Air War College, Maxwell AFB, Ala.
ASSIGNMENTS
1. December 2000-December 2001, Student, Undergraduate Pilot Training, Columbus Air Force Base, Miss.
2. April 2002-October 2002, Student, B-1B Initial Qualification Course, Dyess AFB, Texas
3. October 2002-October 2004, B-1B Pilot, Executive Officer, 9th Bomb Squadron, Dyess AFB, Texas
4. March 2005-March 2009, T-38 Evaluator Pilot, Flight Commander, Wing Flight Safety Officer, 50th Flying Training Squadron, Columbus AFB, Miss.
5. July 2009-December 2012, B-1B Evaluator Pilot, Director of Operations, 34th Bomb Squadron, Ellsworth AFB, S.D.
6. December 2012-December 2013, Student, U.S. Army Command and General Staff College, Fort Leavenworth, Kan.
7. December 2013-December 2015, Director, Course Manager, Joint Targeting School, Dam Neck Naval Air Station, Va.
8. June 2016-June 2018, Commander/T-6 Evaluator Pilot, 41st Flying Training Squadron, Columbus AFB, Miss.
9. June 2018-June 2019, Student, Air War College, Maxwell AFB, Ala.
10. July 2019-June 2021, Director, B-21 Integration and System Management Office, Joint Base Anacostia-Bolling, Washington D.C.
11. June 2021-June 2023, Commander, 28th Operations Group, Ellsworth AFB, S.D.
12. June 2023-Present, Commander, 28th Bomb Wing, Ellsworth AFB, S.D.
FLIGHT INFORMATION
Rating: command pilot
Flight Hours: more than 3,400 hours, including 991 combat hours
Aircraft Flown: B-1B, T-38, T-6, T-37
MAJOR AWARDS AND DECORATIONS
Defense Meritorious Service Medal
Air Force Meritorious Service Medal with two oak leaf clusters
Air Medal with two oak leaf clusters
Aerial Achievement Medal
Air and Space Commendation Medal with oak leaf cluster
Air and Space Achievement Medal with three oak leaf clusters
Legion of Merit with oak leaf cluster
DATES OF PROMOTIONS
Second Lieutenant May 26, 2000
First Lieutenant May 26, 2002
Captain May 26, 2004
Major Dec. 1, 2009
Lieutenant Colonel Jan. 1, 2015
Colonel Dec. 1, 2020
(Current as of June 2023)