EDGEWATER — Edgewater's David James has many stories to tell.
Raised in Woodlawn, James served as a World War II fighter pilot, met the woman of his dreams at a Walgreens lunch counter sit-in, worked for Mayor Harold Washington and became Winnetka's first black homebuyer.
Though his extraordinary 92 years of life are peppered with intimate brushes with celebrities and historical figures, James says his wife and children are what give him the most pride.
On a crisp and sunny afternoon, James sat down with DNAinfo at The Breakers senior community in Edgewater to share some of the many incredible tales that make up his legacy.
From talking civil rights with Louis Armstrong over breakfast, to driving Martin Luther King Jr. to a famous speech in Winnetka, here are a few of James' amazing stories.
1. Being the Only Man of Color at Lane Tech: James was the second person in his family to go to Lane Tech Academic Center; his brother had graduated in 1938. Holding a 1941 Lane Tech yearbook in his hands, James said that year only two people of color were featured in the book. He opened it and proudly identified a young man with a wide smile and parted hair as himself. As he flipped the bookmarked pages to point out the second person of color, he landed on a student-drawn cartoon and laid his finger on the last frame.
"There's the other one," James said, pointing to the cartoon.
In the back of the Lane Tech Academic Center's 1941 yearbook is a cartoon that features an African-American stereotype, whom James referred to as the only other person of color in the yearbook aside from himself.
Though the cartoon is racially insensitive, James said of the cartoonist: "He's a very good friend of mine. He said he'd never seen any blacks, except at the train station ... [He was the] sweetest guy, didn't have a prejudiced bone in his body. But at that point, he had no contact, it was his first time seeing black people."
2. Flying in a Segregated Military During World War II: After James entered his freshmen year of college at Loyola University, he was drafted and joined the Tuskegee Airman, piloting fighter planes and later bombers during World War II for the Army. Stationed in Italy, James flew his single-seater plane alongside only some of his fellow countrymen. At the time, the majority of military units were segregated. He said he never interacted with white comrades. He's been known to wear a shirt that reads, "In 1941 The Military Didn't Want Us To Fly, By 1945 Only The Nazis Didn't Want Us To Fly," he said.
"We knew exactly what we were fighting for," James said. "If Hitler had won the war, where would you be today, and where would I be today?"
In 1946, his tour ended and he returned to Chicago, where he re-enrolled at Loyola.
3. Meeting His Wife at a Downtown Walgreens Sit-In: In 1949, James graduated from Loyola with a bachelor's degree. Soon thereafter he bumped into his eventual wife, Mary, while she was on her way to a sit-in at a State Street Walgreens lunch counter. She asked him to join. Mary was a member of the Congress of Racial Equality, or CORE, a politically influential organization leading sit-ins across the country — some of the first of which were held in Chicago. James said Mary taught him about the group's mission and persuaded him to join.
They spent the remainder of their day at the lunch counter, being ignored by staff and other patrons until the store eventually closed and everyone was asked to leave. Later, she'd inspire him to go to law school, and the couple had six children together.
"My wife was way ahead of me in every regard. She was a lawyer before I met her," James said. "In fact, I went to law school to try to figure out what she was talking about. She had all the brains in the family, she was way ahead of her time in every respect."
4. Eating Breakfast and Talking Politics With Louis Armstrong: In 1963, James was out on the road in Downstate LaSalle-Peru working as a newly minted lawyer tasked with educating federal employers and their contractors that they could no longer discriminate against employees based on race, ethnicity and other personal factors. Two years earlier, President John F. Kennedy had signed Executive Order 10925, effectively creating the Equal Employment Opportunity Commission.
One morning while staying at the local Holiday Inn, James said he was stunned to see a familiar face walking down the corridor toward him.
"Oh my God, Mr. Armstrong!" James said he exclaimed, before offering to buy Louis Armstrong breakfast. The famous jazz musician wanted to pay, but James insisted it would be "his honor" to pick up the tab.
The two talked about everything from Armstrong's performance at a local gym, to the work James was doing promoting integration and civil rights. They both believed there was still much to be done to achieve racial equality, he said.
David James' mother was the first generation on his maternal side to be born free and not into slavery. James holds a picture that shows his mother, aunt, uncle and grandfather in St. Louis, 1900. [DNAinfo/Linze Rice]
5. Driving Martin Luther King Jr. to a Winnetka Speech: On July 25, 1965, Martin Luther King Jr. was due to speak in Winnetka at its Village Green. James' job was to pick up King and bring him to the park. Unsurprisingly, they arrived to protesters. But James said there was something that struck him more than that: 8,000 people, predominantly white, had gathered to hear the reverend speak and support his ideals. A plaque now marks the spot in Winnetka where King delivered his speech, along with the quote, "History has presented us with a cosmic challenge ... We must now learn to live together as brothers, or we will perish together as fools."
James said he and King struck up a friendship after that, and eventually the reverend persuaded James to move to the North Shore suburb. Inspired by the openness of the Winnetka's people during King's speech, and taking the advice of his friend and mentor, James and his family moved to Winnetka in 1967, becoming the city's first black homeowners.
6. Becoming the First African-American Attorney for the American Bar Association: In 1967, James was hired by the American Bar Association — the first black man ever to be an attorney for the organization. The man who gave him that chance, Lewis F. Powell Jr., later served on the U.S. Supreme Court beginning in 1971.
Though James said of Powell, "He was gentle, brilliant, kind, just a delight to know him," he admits he had initial reservations because of Powell's anti-integration efforts in the Brown V. Board of Education case.
James worked at the bar association for 25 years, during which he championed diversity, recruiting racial minorities and helping launch the Council on Legal Education Opportunity. He now considers his tenure as a civil rights lawyer one of his life's greatest professional accomplishments.
His biggest regret, he said, was that he doesn't believe he will "live to see the day" when America will be "a nation binding up people's wounds," when it comes to equality.
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