Biographies of Local Legends

John W. Rogers, Sr. Tuskegee Airman and Judge

By April 13, 2022 No Comments

September 3, 1918 – January 21, 2014

John W. Rogers, Sr., was a Chicago area Attorney, Judge and an original Tuskegee Airman. He was born in Knoxville, Tenn. while the Great War waged in Europe. And he grew up there during a time of segregated water fountains and Jim Crow rules that barred people who looked like him from using whites-only restaurants or drinking fountains.

John’s mother died of pneumonia when he was only 4 and later when he was 12, his father, a barber and minister, died of kidney problems.

He and his sisters then moved to Chicago to live with an uncle, Henry Turner. Mr. Rogers graduated from Tilden Technical High School and earned a bachelor’s degree in education from what is now Chicago State University in 1941.


Aviator, Community Leader, Legal Scholar, Role Model, Mentor and Gentleman

After graduating from Tilden High School, Mr. Rogers attended community college and earned a teaching certificate from Chicago Teachers College. He taught in the Chicago Public Schools until war broke out, then he volunteered, his wife said.

“He always wanted to be a pilot, from when he was a little boy,” she said. “He used to make little airplanes from matchboxes.” From a young age, Rogers dreamed of flying planes and attended the Civilian Pilot Training Program at the former Harlem Airport on the South Side of Chicago. He earned his pilot’s license before enlisting in the U.S. Army Air Corps., and in 1941, became part of the famed 99th Pursuit Squadron of the Tuskegee Airmen.

Before World War II, African-Americans had been barred from flying for the U.S. military. Civil rights groups and black newspapers persuaded the government to create an African-American flight program based in Tuskegee, Ala., and Mr. Rogers became part of the Tuskegee Airmen’s 99th Pursuit Squadron. He was one of the original 28 airmen in the first group to go overseas.

Mr. Rogers was promoted to captain and flew 120 missions in Europe. Years later he was part of a group of about 300 Tuskegee Airmen to be honored with the Congressional Gold Medal. And in January 2012, Mr. Rogers was one of a group of Tuskegee Airmen who came to the White House as a special guest of President Barack Obama to view the movie “Red Tails,” which is a dramatized depiction about the pioneering African-American aviators who served their country with courage and daring despite racism in the military and at home.

Mr. Rogers returned from flying 120 often-dangerous missions for his country to be turned down for admission to the University of Chicago Law School, relatives said. Instead of taking no for an answer, he returned the next day decked out in his captain’s uniform and offered to take any test to get in.

As a member of the 99th Pursuit Squadron, he was one of the first Tuskegee Airmen to go overseas, said Mark Hanson, curator of the Chanute Air Museum in Rantoul, where the 99th Squadron was activated. Based in North Africa, members of the 99th flew over Italy, he said, performing bomb missions and escorting white pilots.

With keen eyesight and steady nerves, Mr. Rogers had a reputation for meticulous preparation and precision. “He was one of the best dive-bomber pilots in that squadron,” Hanson said. Others said, “He could drop a 500-pound bomb through the window of a building.”

He viewed “Red Tails” a few times. His grand-daughter, Victoria Rogers, remembers that when he watched, he moved his hands like he was still flying. “He said he could remember the tension,” she said.

After the war, Mr. Rogers practiced law, eventually partnering with attorney and future judge Earl Strayhorn, as well as Mr. Rogers’ first wife, the former Jewel Stradford, the first AfricanAmerican woman to graduate from the University of Chicago Law School. He later shared office space with prominent attorney Earl Langdon Neal, and he was a trustee of what would become the Metropolitan Water Reclamation District, his wife said. He then served 21 years as a juvenile court judge, Gwen Rogers said. He rose to become a supervising judge.

A number of the youths who appeared before him later wrote him letters thanking him for giving them a second chance, his wife said. One straightened out and formed a church, she said.

Mr. Rogers and his first wife divorced when John Jr. was about 3 years old.

When their son was about 12, “instead of giving him a toy, they invested in some stock for him,” said Chief Judge Timothy Evans of Cook County Circuit Court. Their son later founded Ariel Investments.

“I used to thank Judge Rogers for giving him the stock. I would tell him he gave birth to Ariel, which created an opportunity for me,” said Ariel President Melody Hobson, who in 2013 married filmmaker George Lucas, executive producer of the movie, “Red Tails.”

Mr. Rogers was active with the NAACP, the Urban League, and he sponsored scholarships for law students. In 2007, he and other Tuskegee Airmen were honored at the Capitol and awarded the Congressional Gold Medal. “He was a wonderful, wonderful role model,” Evans said, “moving forward, while giving back, every step of the way.”

“From his service as a Tuskegee Airman to his appointment as a distinguished judge, he was a leader,” said Michael H. Schill, dean of the University of Chicago Law School. “He was so honest,” his wife said. “He was so dependable. He was so generous.”

He stressed punctuality, dependability and aiming high. And he wasn’t above telling family members “You’re a Rogers” as he exhorted them to excellence.

Mr. Rogers enjoyed lamb chops, playing bridge and swimming, as well as travel to Alaska, China, Russia and South Africa. His favorite singers were Johnny Mathis and Luther Vandross.

John W. Rogers, Sr. is buried at Oak Woods Cemetery.

John W. Rogers Sr.’s skill as a pilot for the pathbreaking Tuskegee Airmen was well known. William Thompson, an armament officer and Rogers’ friend, took this photo of Rogers in his P-40 Warhawk—he called Rogers “the best dive-bomber pilot in the business.



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