Dr. Janis Prince, associate professor of sociology and chair of the Department of Social Sciences, celebrates the resiliency and valor of Roy Caldwood during his speech at Saint Leo University. Prince served as moderator for the discussion with Caldwood. Funding for this symposium was made possible in part by a Sociological Research Grant from Alpha Kappa Delta International Sociology Honor Society. (Photo by A.J. Colson, Saint Leo University.)

I had the great honor of joining a presentation featuring legendary 101-year-old WWII veteran Roy Caldwood — the last of the renowned Buffalo Soldiers in the state of Florida — as the keynote speaker, who shared his storied life with an assembly at Saint Leo University (SLU). It was exciting to hear about Caldwood’s experiences from the man himself.

Saint Leo is a “university who has deep ties to our military brothers and sisters, with over 50 years of educating our nation’s military personnel,” stated SLU President Dr. Edward Dadez, who said it was an honor and a privilege to welcome the attendees to an event featuring such a distinguished guest.

Caldwood served our country in Italy from 1943-45 during World War II in the 92nd Infantry Division Reconnaissance Troop 2nd Platoon of the U.S. Army, who were named the Buffalo Soldiers after the 19th-century African American cavalrymen. On April 5, 2023, Tampa Mayor Jane Castor proclaimed that day to be Roy Caldwood Day. Additionally, he’s a recipient of the New York City Department of Corrections Medal of Honor and the U.S. Army Bronze Star.

At the presentation, Caldwood, joined by his daughter, Diane Royer, and other family members, began with how he felt about getting drafted: “So, I thought about it, and I said, ‘Would I be better off if Hitler and Mussolini’ — they called them the Axis back in those days — ‘if they won the war?’ … I said, ‘Hell no. … I’m putting my bet on this country, and I’ll do what I can to help,’ so I went into the Army.”

“I was a premed student, so they took me and 12 others and they put us in what they call a medical sanitation outfit,” said Caldwood.

He was first sent to Henry Patrick, Virginia. He was disappointed, as there was no training to fight in the war there, but he got his chance to do more with the Army when he saw a recruitment ad for the Buffalo Soldiers in the Stars and Stripes military newspaper. He signed up immediately.

“What attracted me was that they’re the Buffalos, guys who are going to be really trained to be real soldiers, and it was an outfit that anyone looked up to,” said Caldwood. “I mean, just the thought of joining the Buffalos really lifted our spirits.”

He told of times where he faced racial prejudice in Henry Patrick, like being forced to move to the last row of a theater by military police, despite his and others’ complaints, and getting put in train seats next to a smoke-filled engine on the way to training in Fort Huachuca, Arizona.

“It was pretty bad. But we didn’t care,” said Caldwood, “because we knew we were going to have a much better life.”

His determination was so great that not even having diarrhea and being stuck in a hospital stopped him from getting out and passing the fitness test to join the 92nd Infantry Division.

When stationed overseas in Italy, was assigned to a reconnaissance troop to track down a batch of Germans. Among Caldwood’s most memorable experiences involved the ‘Purple Heart Stretch,’ where German soldiers hid in the mountains and killed Americans who passed through. When he, two other soldiers, and local women were forced to travel this route for food, they came under fire by mortars. The first mortar missed, but Caldwood assumed the next ones meant death — then the situation became incredible. The next 30-40 mortars all strangely missed, and he realized they were missing on purpose. Their attackers, it turned out, were telling Caldwood’s group they wanted to surrender.

“And about a couple hours later, that last batch of Germans did peacefully surrender to our platoon,” he said.

He has lived a storied life, one where the excitement didn’t end after the war, such as his time at the New York City Department of Corrections on Rikers Island as an assistant deputy warden and program director from 1955-76 — during which he survived a hostage situation by the Black Panthers. At 101 years old, he’s still physically active, doing things like dancing on a yacht and helping train his grandson in 2023. And he’s not done yet.

If you’d like to learn more about this hero, check out his book, Making the Right Moves: Rikers Island & NYC Corrections.

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Taylor Wells
Taylor Wells is a relatively recently hired news reporter for the Osprey Observer, having been with the paper only since October 8, 2018. Aside from writing articles, he helps edit and upload them to the Osprey Observer site, and is always available to help other staff members in his spare time. He graduated from Saint Leo University with a bachelor’s degree in professional writing and lives in Valrico.