Robert Friend, a retired U.S. Air Force pilot who participated in 142 combat missions during World War II as a member of the illustrious Tuskegee Airmen, died of sepsis last Friday, June 21, at the age of 99. Friend’s daughter, Karen Crumlich, told local CNN affiliate station KCBS that her father—among the last remaining members of the country’s first group of all-black military aviators—was surrounded by friends and family when he died at a Long Beach, California, hospital.

Col. Friend, a veteran of World War II, the Korean War and the Vietnam War, enjoyed a distinguished 28-year military career. According to Harrison Smith of the Washington Post, he applied to join the newly created African-American aviation program at Alabama’s Tuskegee Institute in 1942, then went on to serve with the 301st Fighter Squadron of the 332nd Fighter Group in the North African and European theaters, accruing honors including the Bronze Star Medal, the Air Medal and the Distinguished Flying Cross. Following the war’s conclusion, Friend acted as an operations officer in Korea and Vietnam; worked on early rocket programs; and led Project Blue Book, a classified Air Force study of unidentified flying objects.

Born on February 29, 1920, in Columbia, South Carolina, Friend had dreamed of being a pilot since childhood. Undeterred by the military’s refusal to accept black airmen, he took aviation classes at Pennsylvania’s Lincoln University and earned his private pilot’s license through the Civilian Pilot Training Program. When the so-called “Tuskegee Experiment” began, Friend was quick to enlist, becoming one of around 1,000 black aviators (in addition to almost 14,000 black navigators, bombardiers, instructors, aircraft and engine mechanics, control tower operators, and miscellaneous maintenance and support staff) involved in the initiative. As History.com notes, the Tuskegee Airmen participated in more than 15,000 sorties across the European and North African theatres, earning a collective 150 Distinguished Flying Crosses and paving the way for wider integration within the military.

Per CAF Red Tail Squadron, a non-profit dedicated to preserving the Tuskegee Airmen’s legacy, Friend was a combat operations officer tasked with planning and organizing his squadron’s strategic and tactical air missions. Skilled at flying both P-47s and P-51 Mustangs—his, complete with the red rudder, nose and wing tips commonly associated with the elite group of airmen, was nicknamed “Bunny” in honor of his then-girlfriend—he served as a wingman for Benjamin O. Davis Jr., a Tuskegee commander who later became the Air Force’s first black general.

The Post’s Smith writes that Friend narrowly escaped disaster twice in the span of just two weeks: On December 14, 1944, a German oil barge he had targeted sparked an enormous explosion that almost grounded his own aircraft—an experience he told the Pittsburgh Courier “was sort of like being in hell.” Days later, he was forced to jump ship due to poor weather and mechanical problems and soon found himself parachuting straight toward a knife-wielding woman roaming the Italian mountains. Luckily for Friend, she was not a Nazi sympathizer, but rather a desperate local hoping to take his silk parachute.

After the war, Friend completed his studies at the Air Force Institution of Technology. Between 1958 and 1963, he oversaw the U.F.O.-centered Project Blue Book, which he unsuccessfully campaigned to have moved under the purview of a non-military government agency such as N.A.S.A. At a 2012 lecture in Las Vegas titled “Military U.F.O.s: Secrets Revealed,” the lieutenant colonel commented, “I, for one, also believe that the probability of there being life elsewhere in this big cosmos is just absolutely out of this world,” adding, “I think the probability is there.”

According to the Desert Sun’s Sherry Barkas, Friend started an aerospace company upon his retirement from military service. He worked there until about a year ago and spent his free time appearing at speaking engagements around the area. One of his favorite local hang-outs was the Palm Springs Air Museum, which holds a restored P-51 Mustang painted to mimic the “Bunny” plane flown by Friend during World War II.

Friend worked to keep the memory of the Tuskegee airmen alive until the end. At age 98, he still traveled to between 20 and 30 locations per year to speak about the two-pronged battle the Tuskegee airmen faced, as well as how he fought fascism overseas and racial segregation at home. At one speaking event, a teenage boy posed a question Friend had been asked many times before: “Why would you go and fight for a country that didn’t fight for you?”

According to Dennis McCarthy of the Los Angeles Daily News, Friend replied, “Because I’m an American, and it was the right thing to do.”