John Cherrey was born in 1966 in New Jersey. He was commissioned a 2d Lt through the Air Force ROTC program at the Stevens Institute of Technology in New Jersey on May 27, 1988, and went on active duty beginning March 4, 1989. Lt Cherrey completed Undergraduate Pilot Training and was awarded his pilot wings at Vance AFB, Oklahoma, in March 1990, and then completed lead in fighter training and A-10 Thunderbolt training before serving with the 74th Tactical Fighter Squadron at England AFB, Louisiana, from October 1990 to April 1992. His next assignment was as an OA-10 pilot and training officer with the 19th Tactical Air Support Squadron at Osan AB, South Korea, from May 1992 to September 1993, followed by service as assistant chief of Stan/Eval with the 52nd Operations Group at Osan AB from October 1993 to May 1994. Capt Cherrey next served as a project manager and A-10 operational test and evaluation pilot with the 422nd Test and Evaluation Squadron at Nellis AFB, Nevada, from July 1994 to March 1997. During this time he in support of Operations Southern Watch from 1995 to 1997. He attended the USAF Weapons Instructor Course at Nellis AFB from July to December 1996, and then served as assistant director of operations for the 81st Fighter Squadron at Spangdahlem AB, Germany, from April 1997 to May 2000, flying in support of operations in Kosovo during 1999. After attending Army Command and General Staff College at Fort Leavenworth, Kansas, Col Cherrey served with Headquarters U.S. Air Force at the Pentagon from June 2001 to April 2003. He served as assistant director of operations, operations officer, and then commander of the 81st Fighter Squadron at Spangdahlem AB from April 2003 to June 2006, and then attended National War College at Fort McNair, Washington, D.C., from August 2006 to June 2007. During his time with the 81st FS, he flew combat missions in Afghanistan in support of the War on Terrorism. Col Cherrey then served as director of the Air Force Element at Army Command and General Staff College at Fort Leavenworth from June 2007 to May 2009. He served as commander of the 451st Expeditionary Operations Group at Kandahar Airfield, Afghanistan, from June 2009 to June 2010, and then as Commander of the 355th Fighter Wing at Davis-Monthan AFB, Arizona, from June 2010 to June 2012. His next assignment was as Chief of Concepts, Strategy and Wargaming in the Directorate of Operations, Plans and Requirements, at the Pentagon from June 2012 to July 2013, followed by service as Deputy Director of Intelligence, Operations and Nuclear Integration for Flying Training at Headquarters Air Eduction and Training Command (AETC) at Joint Base San Antonio-Randolph, Texas, from July 2013 to October 2014. Brig Gen Cherrey's final assignment was as Director of Intelligence, Operations and Nuclear Integration with Headquarters AETC from October 2014 until his retirement from the Air Force on November 1, 2017.

His Silver Star Citation reads:

Captain John A. Cherrey distinguished himself by gallantry in connection with military operations against an armed enemy of the United States near Novi Sad, Serbia, from 27 March 1999 to 28 March 1999. During this period, as overall Combat Search and Rescue Task Force Mission Commander and Sandy flight lead, Captain Cherrey courageously and repeatedly risked his life to rescue a fellow American pilot, shot down over hostile Serbian territory. With minimal time for mission planning, Captain Cherrey flew into the teeth of the Serbian air defenses, battling constant communication jamming and intrusion, deteriorating weather, repeated illumination by deadly SA-3 and SA-6 surface-to-air missile systems, and the threat from enemy aircraft only a few miles from the downed pilot's location. At extreme risk to his life, Captain Cherrey overflew unknown Serbian territory, fully exposed to surface-to-air threats, until he positively identified the pilot and his location. Captain Cherrey then orchestrated a plan to bring the rescue helicopters to the pilot's position, while providing them maximum protection. He deceived enemy radar and concealed the intended pickup site by maneuvering his formation away from the downed pilot's position and into the SA-3 and SA-6 lethal ranges, valiantly risking his life. Now critically low on fuel, Captain Cherrey refused to abandon his post. With impeccable courage, he stayed in an increasingly aggressive environment to be near the downed pilot until minutes before his rescue. By his gallantry and devotion to duty, Captain Cherrey has reflected great credit upon himself and the United States Air Force.