Oscar L. Kennedy
February 9, 1926 – February 8, 2023
Class: 43-F-SE
Graduation date: 6/30/1943
Rank at time of graduation: 2nd Lt.
Unit: 477th Bombardier Group
Service # 2nd Lt.
From: Chicago, IL
Oscar Lawton Wilkerson, Jr., better known as “Wilk,” grew up in Chicago Heights adoring planes and went on to become one of the first African American pilots in the United States Armed Forces.
Mr. Wilkerson was a senior at Bloom High School in Chicago Heights when he registered for the Army Air Force. He passed a test and 10 days after graduation found himself on a train to Tuskegee, Alabama, to start training.
He rode a Pullman sleeper car but upon crossing the Mason-Dixon line was directed to a Blacks-only car. Mr. Wilkerson called that his “first real hard taste of segregation,” during an interview with Chicago’s Pritzker Military Museum & Library.
He had a similar experience on a bus in Alabama despite being in uniform.
“It was pretty devastating for him that he had gone through all this training as a pilot and was ready to put his life on the line for his country, and he was told to go to the back of the bus,” Rapier said. “He got emotional at retelling that story.”
Despite his training, job options were limited upon returning to Chicago.
“After the war, we were not able to go into commercial aviation,” Mr. Wilkerson told the military museum. “Blacks weren’t accepted at that time. I couldn’t fly commercially. So, I became a bus driver in Chicago.”
The Chicago chapter of Tuskegee Airmen Inc. was named after the extinct dodo bird because its aviators “had their wings but could not fly,” Rapier said.
“The Tuskegee Airmen was his heart because that’s who he was. He was an original Tuskegee Airman,” said Ken Rapier, who is dedicated to preserving Wilk’s and the group’s legacy as president of the Chicago “DODO” Chapter of Tuskegee Airmen.
Until Wilk’s last moments, he served as the second vice president for the “DODO” chapter. Rapier said Wilk took pride in visiting schools and attending community events to introduce the young generation to aviation.
“Wilk would have the kids reciting the Tuskegee Airmen slogan with him: ‘With courage and determination, I can come adversity,’” Rapier said.
While Wilkerson is best known for being a bomber pilot during World War II, he couldn’t get a job as an airline pilot right after the service as Black airmen faced discrimination.
But he still broke barriers when he returned home.
“He was the first African American to be hired as a bus driver for Safeway bus company,” Rapier said.
Afterward, Wilkerson gravitated to his love for radio and jazz music and was behind a program called “Weekend Wilkie.”
While Wilk was a man of many talents and interests, Rapier told WGN News that the Tuskegee Airman will always be remembered as someone who served his country and helped pave the way for others.
“He was a very intelligent man and the constant gentleman,” Rapier said. “Everyone who knew Wilk loved him. He was just a wonderful person.”
Sources:
Chicago Sun Times
WGN9.com
Findagrave.com
