Chief Master Sergeant Joseph O. Caulfield is the Command Chief of the 105th Airlift Wing, Stewart Air National Guard Base, Newburgh, New York. He serves as the wing’s senior enlisted leader and principle advisor to the wing commander on matters impacting the health, morale, welfare, readiness, professional development, and effective utilization of the enlisted force. 

Chief Caulfield enlisted in the Air Force on September 1, 1983. As a jet engine mechanic, he was initially assigned to the 49th Fighter Interceptor Squadron at Griffiss Air Force Base (AFB), New York. In 1994 he became a member of the New York Air National Guard at Stewart 
Air National Guard Base (ANGB), New York. Shortly after joining the wing, he cross-trained to the loadmaster career field, ultimately achieving evaluator status on both the C-5A and, later, the C-17A aircraft. Prior to his current position, Chief Caulfield served as the 105th Operations Group Superintendent. 

Chief Caulfield has accumulated over 6,500 flight hours. He has flown special assignment, and combat missions in support of Operations NORTHERN WATCH, DESERT STORM II, IRAQI FREEDOM, ENDURING FREEDOM, NEW DAWN, UNIFIED ASSISTANCE, RESOLUTE SUPPORT, FREEDOM’S SENTINEL, and INHERENT 
RESOLVE. Chief Caulfield has a law enforcement background, operating in a civilian capacity as a correctional sergeant and police officer.

1986 Noncommissioned Officer Preparatory course, Griffiss Air Force Base (AFB), N.Y. 
2001 Bachelor of Science, Cum Laude, Organizational Management, Manhattan College, Riverdale, N.Y. 
2002 Noncommissioned Officer Academy, Maxwell AFB, Ala., by correspondence 
2004 Senior Noncommissioned Officer Academy, Maxwell AFB, Ala., by correspondence 
2016 Associate of Applied Science, Air Operations, Community College of the Air Force, Maxwell AFB, Ala. 

1. September 1983 – October 1983, Basic Military Training, Lackland Air Force Base (AFB), Texas 
2. October 1983 – January 1984, Jet Engine Technician School, Chanute AFB, Ill. 
3. January 1984 – April 1987, Aerospace Propulsion, Griffiss AFB, N.Y. 
4. September 1994 – October 1995 Aerospace Propulsion, Stewart Air National Guard Base (ANGB), N.Y. 
5. October 1995 – February 1996, C-5 Loadmaster course, Altus AFB, Okla. 
6. February 1996 – February 2011, C-5 Loadmaster, Stewart ANGB, N.Y. 
7. February 2011 – May 2011, C-17 Loadmaster course, Altus AFB, Okla. 
8. May 2011 – October 2014, Noncommissioned Officer in Charge, Current Operations Scheduler, 137th Flying Squadron, Stewart ANGB, N.Y. 
9. October 2014 – June 2019, Flight Chief, 137th Flying Squadron, Stewart ANGB, N.Y. 
10. June 2019 – November 2019, Superintendent, 105th Operations Group, Stewart ANGB, N.Y. 
11. November 2019 – Present, Command Chief Master Sergeant, 105th Airlift Wing, Stewart ANGB, N.Y. 

Rating: Senior Enlisted Aircrew 
Flight hours: more than 6,500, including 960 combat hours 
Aircraft flown: C-5A and C-17A 

Meritorious Service Medal 
Air Medal with three oak leaf clusters 
Aerial Achievement Medal with three oak leaf clusters 
Air Force Commendation Medal with two oak leaf clusters 

1983 Honor Graduate, Aircraft Jet Engine Technical School 
1992 New York State Department of Correctional Services Academy 
2002 New York State Department of Correctional Services Sergeant’s Academy 
2006 Charlotte Mecklenburg Police Academy 
2017 SNCO of the quarter, 137th Flying Squadron 
2017 FEMA certified, chaplains disaster response course 
2019 SNCO of the quarter, 105th Operations Group 

Chief Master Sergeant June 1, 2019

(Current as of March 2021)