Proving Them Wrong: Leadership Lessons from a Tuskegee Airman

Col. James Harvey and other Black WWII veterans provide insights for local government leaders about public service and resilience

Today’s newsletter is 1,359 words, a 5-6 minute read.

Diversity, Equity, and Inclusion (DEI) initiatives are under fire across the country, facing scrutiny and political pushback. But let’s be clear — embracing diversity isn’t about checking a box. It’s about recognizing talent, fostering opportunity, and valuing the full humanity of those who serve. And that has always been a mark of great leadership.

At the 2024 Servant Leadership Conference,¹ we heard from Colonel James Harvey, one of the last surviving Tuskegee Airmen, and SGR’s Wendle Medford, whose grandfather, a Black Navy veteran, served during World War II and the Korean War. Their stories remind us that true leadership is tested in adversity — and that those who rise above barriers often transform institutions from the inside out.

Col. James Harvey

Harvey and his fellow Tuskegee Airmen weren’t supposed to succeed. The system was designed to see them fail. Yet they outperformed expectations at every turn, forcing the military to recognize their excellence — even if it took decades.

For today’s leaders in local government, the lesson is clear: Progress doesn’t happen by accident. It happens when people, in the face of resistance, choose to lead with conviction, integrity, and belief in the worth of others.

Fighting Two Wars: The Battlefield and the Homefront

During World War II, Black service members weren’t just fighting against the Axis powers abroad — they were also battling racism and segregation at home. The Double V Campaign, launched by the Pittsburgh Courier, one of the leading African American newspapers of the time, captured this dual struggle: Victory abroad against fascism, and victory at home against Jim Crow.

For Col. Harvey, the motivation to serve was simple: He wanted to fly.

“I was 10 years old at the time, and I was in my front yard,” he recalled. “We lived in a rural area in northeastern Pennsylvania, and I heard this noise. I looked up — it was a flight of P-40s (from a nearby base). And I said, ‘I’d like to do that one day.’ That was it.”

Becoming a pilot in the segregated U.S. military was anything but simple. Wendle cited a 1925 Army War College report that openly doubted the capabilities of Black soldiers, claiming they were “inferior in mentality” and “weren’t fit for duty.”

Harvey and the Tuskegee Airmen proved them wrong.

“The white cadets, all they had to do was demonstrate they could get the aircraft off the ground and back on safely. Not us,” Harvey said. “We had to learn to fly the aircraft, different maneuvers. Everything had to be perfect for us because they were trying to wash us out. But we proved them wrong. We did it.”

While the Tuskegee Airmen fought in the skies, Black service members in other branches faced their own struggles. Matthew Caldwell, Wendle’s late grandfather, was relegated to dangerous, labor-intensive support roles.

“One of his first duties was to gather remains of U.S. sailors and package them, prepare them for burial,” Wendle said. “He was relegated to support roles, not combat roles.”

Black sailors were given high-risk assignments without proper training, a reality that led to catastrophic consequences, most notably the Port Chicago disaster of 1944, where hundreds of Black sailors were killed in a munitions explosion.

Wendle Medford, right, and Mike Mowery at the 2024 Servant Leadership Conference.

Despite the discrimination, these service members excelled. The Tuskegee Airmen’s performance in combat was unmatched.

“We knew what the aircraft could do, and we knew what we could do in the aircraft,” Col. Harvey said. “So, you can’t beat that combination.”

Their success forced the military — and eventually the country — to acknowledge a truth that should have been obvious all along: Talent and leadership aren’t limited by race.