Dave Winn was born in Austin, Minnesota, on July 20, 1923. He enlisted in the Aviation Cadet Program of the U.S. Army Air Forces on March 24, 1942, and was commissioned a 2d Lt and awarded his pilot wings on February 16, 1943. Lt Winn flew 54 combat missions in B-26 Marauder bombers with the 319th Bomb Group and 13 combat missions in P-38 Lightning reconnaissance aircraft with the 32nd Photo Reconnaissance Squadron in the Mediterranean Theater between November 1943 and October 1944. He then transferred to Williams Field, Arizona, where he served as a gunnery instructor until leaving active duty on November 12, 1948. Winn then joined the Minnesota Air National Guard, and was recalled to active duty on March 1, 1951. He served with the 109th Fighter Interceptor Squadron at Snelling AFB, Minnesota, from March 1951 to August 1952, and then with the 526th Fighter Bomber Squadron (later redesignated the 526th Fighter Interceptor Squadron) at Landstuhl AB and then at Neubiberg, West Germany, from September 1952 to August 1955. Capt Winn then transferred to the 94th Fighter Interceptor Squadron at Selfridge AFB, Michigan, in September 1955, where he served until November 1957, when he entered the Bootstrap program to earn his degree. He graduated with a Bachelor's degree in Journalism from the University of Minnesota in July 1958, and then served with the 94th FIS until September 1958, when he transferred to Headquarters Air Defense Command at Ent AFB, Colorado. Maj Winn served there until July 1962, when he went to England to serve as an exchange pilot with the Royal Air Force. Col Winn returned to the U.S. in May 1964, and served at Headquarters U.S. Air Force in the Pentagon from June 1964 to June 1966. He attended National War College from July 1966 to June 1967, and then completed F-105 Thunderchief Combat Crew Training before being assigned as Assistant Deputy Commander for Operations of the 355th Tactical Fighter Wing at Takhli Royal Thai AFB, Thailand, in March 1968. Col Winn was shot down on April 15, 1968, and was rescued, but was shot down a second time on August 9, 1968, and was captured by the North Vietnamese. After spending 1,678 days in captivity, he was released during Operation Homecoming on March 14, 1973. He was briefly hospitalized to recover from his injuries at Scott AFB, Illinois, and then served as Vice Commander of Sheppard Technical Training Center at Sheppard AFB, Texas, from August 1973 to August 1974. He was Deputy Commander of the 22nd North American Aerospace Defense Command (NORAD) Region at Canadian Forces Base North Bay in Ontario, Canada, from August 1974 to August 1976, and then served as Chief of Staff at Headquarters NORAD, Peterson AFB, Colorado, from August 1976 to May 1977. Gen Winn's final assignment was as Commander of the NORAD Combat Operations Center in Cheyenne Mountain, Colorado, from May 1977 until his retirement from the Air Force on July 1, 1978. Dave Winn Flew West on September 25, 2009, and was buried at Lakewood Cemetery in Minneapolis, Minnesota.

His 1st (of 2) Silver Star Citation reads:

For gallantry in connection with military operations against an opposing armed force as the Pilot of an F-105D Thunderchief of the 357th Tactical Fighter Squadron, 355th Tactical Fighter Wing, Takhli Royal Thai Air Base, Thailand, on 23 June 1968. On that date, Colonel Winn was instrumental in effecting the rescue of his wingman, downed by hostile ground fire, in the Gulf of Tonkin. With complete disregard for his own safety, he continued to make numerous aggressive passes up and down the extremely well-defended coast of North Vietnam until the safe recovery of his wingman could be effected. By his gallantry and devotion to duty, Colonel Winn has reflected great credit upon himself and the United States Air Force.