Colonel William James "Greg" Gregory

Colonel William James “Greg” Gregory, U.S.A.F., retired, was born in Smith County, Tennessee on August 5, 1920. Growing up in middle Tennessee he was part of the inaugural year of Middle Tennessee State University’s aviation program (1940/41); a first flight that would begin an extraordinary flying career.

In the summer of 1941, Gregory joined the Army Air Corps’ aviation program as a Cadet Pilot, just three months before the start of World War II. After completion of flight training at Randolph Field, San Antonio, he was assigned to the 49th Fighter Squadron (P-38 Lightning, “Mr. 5x5”), as part of the North Africa Campaign, completing 50 combat missions by 1943.

Master Pilot: As a Command pilot, Col. Gregory is also a combat veteran of the Korean War and served two tours in Viet Nam, with a 35-year military career spanning some of the most significant chapters of the development of aviation. He piloted 55 different airplanes while in the Air Force, including a number of aircraft flown with the US Navy. Col. Gregory is one of a few Air Force pilots to attain Aircraft Carrier Qualification, earned from the deck of the USS Lexington, and later commanded a classified U-2 project with U-2 deploying from the deck of the USS Ranger. It was during this mission that he earned his “Shellback card” upon crossing the equator.

High Altitude Reconnaissance: In the late 1950s Gregory commanded Lockheed’s classified RB-57 squadron, the “Black Knight Project,” flying missions along the border of Russia during the early stages of the Cold War, and later overflights of VietNam. Gregory was among the first pilots to fly above 65,000 feet, a group of pilots referred to as “Stratonauts.”

The Cuban Missile Crisis: An important chapter of Col. Gregory’s career followed the shoot down, capture and conviction of U-2 pilot Francis Gary Powers in Russia. In 1960, after the Powers incident forced the relocation of his next high-altitude assignment, Greg was sent to Edwards Air Force Base where he was selected to Command WRSP-IV (Weather Reconnaissance Special Project); the Air Force/CIA collaborative U-2 squadron located in the remote North Base at Edwards, in the Mojave Desert. This squadron, under Gregory’s command, provided the first photographs proving the presence of Soviet SAM missiles and Soviet build-up in Cuba. The photographs resulting from these missions provided President Kennedy and his cabinet with the evidence needed to successfully pursue a diplomatic path to resolving a situation in which the US was fully within the range of the nuclear ICBMs’ reach. These photographs were shared on the floor of the United Nations, bringing an end to the Cuban Missile Crisis.

During this period of his career, Col. Gregory worked closely with Kelly Johnson, the highly revered Lockheed aeronautical engineer and designer of the U-2 and SR-71. Gregory and his pilots provided frequent feedback contributing to the refinement of this high-altitude reconnaissance aircraft and its photographic capability.

As a result of Col. Gregory's command of this U-2 project, he was awarded the CIA's Medal of Merit* by CIA Director, Lt. General Marshall Carter, his second (of four) Legion of Merit**, and a personal letter of commendation from President John F. Kennedy. Following the award presentation in a secure ceremony, the medal was taken to CIA Headquarters in Langley, and was returned to Col. Gregory when his involvement in the Cuban Missile Crisis was de-classified in 1975.

Col. Gregory's continued command of top secret U-2 missions provided surveillance images detailing the mounting tension in Viet Nam.

Upon completion of his assignment with WRSP-IV, Col Gregory was selected as one of only 30 joint-services senior officers identified each year for The National War College at Ft. McNair, Washington DC; the senior service educational program for the joint services. Earning his Master’s degree in foreign affairs at George Washington University during this same period, Col. Gregory was assigned to the Pentagon following course completion. During his assignment to the Pentagon from 1966-71, Col. Gregory worked in the area of research and development, focusing on the design of the first drone concepts while serving as Chairman of the United Nations Committee on Reconnaissance, in Brussels, Belgium.

Col. Gregory’s final Air Force assignment was as Vice-Commandant of the Air Force Institute of Technology at Wright-Patterson Air Force Base, retiring from active duty in 1975.

Col. Gregory holds the rare distinction of being awarded four Legions of Merit** throughout his career for his exceptional service to the Air Force.

Following his retirement from the Air Force, Col. Gregory and wife Helen moved to Austin where he worked for the State of Texas for 15 years as the Deputy Director of Workers Compensation and remained active in a number of military organizations including, Daedalions, The Eagles Association, and The Retired Officers Association.

In the year 2000, at the age of 80, Col. Gregory became a licensed glider pilot and enjoyed this new chapter of flight for the next 8 years. From the age of 72 to 94 Greg cycled around the world, crossing a different country every two years.

His community activities included 20 years of weekly Meals on Wheels deliveries, service to the Board of the Scholarship program he founded at the University of Texas at Austin through the LAMP Program, the Finance Committee of Highland Park Baptist Church, and a number of other professional and educational organizations.

In 2016, Greg assisted author Robert Richardson in writing the book entitled, The Jagged Edge of Duty about the World War II era of the 49th Fighter Squadron, of which Greg was the oldest remaining member. In 2018 author Robert Richardson completed the writing of the book Eagle 5 X 5 that is a biography of Greg’s life. In March 2020 Robert Richardson wrote a second biography on Greg, focused on Greg’s military career entitled, Spying from the Sky (Amazon).

Col. Gregory was married to the late Helen Dwire Gregory for 47 years until her death in 1990. He was a man led by his faith, optimism, integrity, commitment to his country and his deep love for his family. While an extraordinary and decorated pilot, he was also a loving and devoted father, grandfather and great-grandfather.

Col. Gregory is survived by his two daughters Gretchen Gregory Davis (husband Dr. Gene L. Davis, son Gregory A. Davis) and Cookie Gregory Ruiz (husband Lt. Col. Philip E. Ruiz, USAF, Ret., daughters J.R., husband Jaxson Warrick, children Parker and Wade; and Boo, husband Kyle Wong).

The memorial service for Col. Gregory will be held on Tuesday, October 19th at 10:30am at The Church at Highland Park (5206 Balcones Drive, 78731), with burial to follow at Austin Memorial Park. Visitation will be held on Monday, October 18th from 3-5:30pm at Weed, Corley, Fish Funeral Home (3125 N. Lamar, 78705)

For those wishing to make a donation in Col. Gregory’s honor: Central Texas Food Bank or Meals on Wheels Central Texas.