Winning a Super Bowl is something that very few people have ever, and will ever, accomplish. Even fewer people can say they were an Air Force pilot who saw combat and flew over 40 sorties before winning the big game.
In fact, defensive tackle and Air Force Captain Chad Hennings is likely the only combat Air Force pilot to win multiple Super Bowls.
Hennings was with the Cowboys for their Super Bowl victories in games XXVII, XXVIII, XXX. Before that, Hennings went to the Air Force Academy and was set to be a pilot. After a standout college football career, Hennings was drafted by the Cowboys in the 11th round, despite the fact that it looked like he was going to be serving eight years.
According to Wikipedia:
After graduating from the U.S. Air Force Academy in June 1988, Hennings entered undergraduate pilot training at Sheppard Air Force Base, Texas, as part of the Euro-NATO Joint Jet Pilot Training (ENJJPT) Program conducted by the 80th Flying Training Wing. The ENJJPT was considered an elite program, and when his ground training studies faltered (he had been an honor student at AFA), his squadron commander isolated him from all contact regarding the Dallas Cowboys, who had drafted him in April 1989. After UPT, Hennings completed Lead-In Fighter Training and because of his size, was eligible only for F-111, F-15 Eagle, or A-10 Thunderbolt II RTU. He became an A-10 pilot and was assigned to the 92d Tactical Fighter Squadron, a unit of the 81st Tactical Fighter Wing based at RAF Bentwaters in the United Kingdom, in June 1990.
While with the 92d TFS, Hennings deployed twice to the Persian Gulf. From April to June 1991, and October 1991 to January 1992, based at Incirlik Air Base, Turkey, Henning flew 45 A-10 missions in support of Operation Provide Comfort, an effort that helped provide relief and humanitarian aid to Kurdish refugees in northern Iraq. He was twice awarded the Air Force Achievement Medal, a humanitarian award and an Outstanding Unit Award for his actions in the service. He was promoted to captain on June 1, 1992.
After the conclusion of the Gulf War, Hennings was permitted to waive his remaining years of service due to a massive decrease in the size of the United States military.
Hennings was able to play for the Cowboys, and the rest is history. Hennings continued to serve his country in the US Air Force Reserve for another nine years while he played football.