Dick O'Grady was born on December 2, 1937, in Waterloo, Iowa. He was commissioned a 2d Lt in the U.S. Air Force through the Air Force ROTC Program at Drake University in Des Moines, Iowa, on June 6, 1960, and went on active duty beginning on August 3, 1960. Lt O'Grady attended Primary Pilot Training at Bartow AB, Florida, from August to December 1960, and Basic Pilot Training at Reese AFB, Texas, from January to September 1961. His first assignment was as a C-130 Hercules pilot with the 345th Troop Carrier Squadron at Sewert AFB, Tennessee, from November 1961 to May 1962, and then with the same squadron based at Naha AB, Okinawa, from June 1962 to January 1963. He then served as a C-130 pilot with the 35th Troop Carrier Squadron at Naha AB from January 1963 to December 1964, followed by service with the 6315th Operations Group at Naha AB from December 1964 to September 1965. During this time he was attached as an Air Liaison Officer with the 1st Special Forces Group at Camp Sukiran, Okinawa, and also participated in the Dominican Civil War. Capt O'Grady attended Pilot Instructor Training from October to December 1965, and then served as a T-37 Tweet Instructor Pilot with the 3641st Pilot Training Squadron at Laredo AFB, Texas, from December 1965 to November 1966. His next assignment was as a Flight Examiner with the Stan/Eval Division, Headquarters, 3640th Pilot Training Wing at Laredo AFB from November 1966 to May 1967, followed by service as a T-37 Flight Training Instructor, Stan/Eval Board Member, and Flight Examiner with the 3251st Flying Training Squadron at Perrin AFB, Texas, from June 1967 to June 1971. He next attended Army Command & General Staff School at Fort Leavenworth, Kansas, from June 1971 to June 1972, followed by service as an A-37 Dragonfly pilot, A-37 Advisor with the South Vietnamese Air Force in Saigon, South Vietnam, from July 1972 to March 1973. Major O'Grady next served as an Staff Officer with 13th Air Force at Udorn Royal Thai AFB, Thailand, from March to December 1973, and then as a T-38 Instructor Pilot with the 86th Flying Training Squadron at Laughlin AFB, Texas, from January 1974 to November 1975, and then as a T-38 Stan/Eval Officer with Headquarters Air Training Command at Randolph AFB, Texas, from December 1975 to April 1977. Lt Col O'Grady next served as Operations Officer for the 560th Flying Training Squadron at Randolph AFB from May 1977 to July 1979, followed by service as Commander of the 560th Flying Training Squadron from July 1979 to July 1980. He served as Director of Pilot Training at Headquarters Air Training Command at Randolph AFB rom August to December 1980, and then as Director of Operations with the 47th Flying Training Wing at Laughlin AFB, Texas, from January 1981 to May 1982. Col O'Grady next served as Commandant of the Squadron Officer School at Maxwell AFB, Alabama, from June 1982 to July 1985, followed by service as Vice Commander of Keesler AFB, Mississippi, from August 1985 to May 1986. He served as Director of Stan/Eval at Headquarters Air Training Command at Randolph AFB from June 1986 to August 1987, and then as Assistant Deputy Chief of Staff for Operations and Readiness at Headquarters Air Training Command from September 1987 until his retirement from the Air Force on February 1, 1989. Dick O'Grady Flew West on July 15, 2018, and was buried at the Grand River Cemetery in Grand River, Iowa.

His 1st (of 2) Legion of Merit Citation reads:

Colonel Richard E. O'Grady distinguished himself by exceptionally meritorious conduct in the performance of outstanding services to the United States as Commandant, Squadron Officer School, Air University, Maxwell Air Force Base, Alabama, from 1 June 1982 to 1 July 1985. During this period, Colonel O'Grady's exceptional leadership directly influenced over twelve thousand Air Force officers. He directed sweeping changes in the Squadron Officer School curriculum to provide company grade officers with the writing, speaking, and leadership skills they need in today's Air Force. Most significantly, his creative improvements allowed our students to focus on examples of courageous leadership while reinforcing their unique heritage as American warriors. The superior initiative, outstanding leadership, and personal endeavor displayed by Colonel O'Grady reflect great credit upon himself and the United States Air Force.