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HomeAt Home & BeyondRoy Caldwood: A Living Legend

Roy Caldwood: A Living Legend

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On Thursday, Oct. 26, Saint Leo University held a symposium to honor Bronze Star recipient Roy J. Caldwood. He was a soldier in the 92nd Infantry Division of the United States Army during World War II, which was comprised entirely of African-American soldiers. His division was known as the “Buffalo Soldiers” in reference to the 19th-century African-American cavalrymen. Staff and students met at the Student Community Center to pay tribute to and hear stories from the 101-year-old veteran.

Earlier this year, Caldwood received the Mayor of Tampa Proclamation declaring April 5, 2023, as Roy Caldwood Day and was awarded the New York City Department of Corrections Medal of Honor. The legend received introductions from various faculty members at the university, including Dr. Janis Prince, chair of the Department of Social Sciences and Saint Leo President Dr. Edward Dadez.

“Mr. Roy Caldwood, at the remarkable age of 101, stands as a living testament to the values of resilience and valor…” Dr. Dadez said. “Mr. Caldwood’s journey, like that of the buffalo soldiers of the 19th century, is one of unyielding courage and sacrifice… It’s not only his accolades that bring him here today, it’s his spirit, his indomitable will, and his dedication to the principles of duty and honor.”

Anthony DeSantis, the Associate Vice President of Student Affairs at Saint Leo, echoed Dr. Dadez in noting that the university has been serving student veterans for the last 50 years and is one of the “top military-friendly schools.” Saint Leo has an entire month of events like the one on Thursday that display this sort of dedication. Caldwood was a speaker of particular note to DeSantis as his grandfather served in the same branch in Italy as the 101-year-old veteran.

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Caldwood was recognized by the National Buffalo Soldier Organization as the last known Buffalo Soldier in the state of Florida and wrote his own book titled “Making the Right Moves.” Caldwood’s biographical novel focused on his time as an assistant deputy warden at Rikers Island and his experience during some of the riots at the infamous correctional facility. There were tables set up along the walls of the room for a book signing after the event and some with memorabilia and information regarding the war, the buffalo soldiers and Caldwood. The living legend delved into some of these topics once he stepped up to the microphone.

Buffalo soldiers of the 25th Infantry, some wearing buffalo robes,
Ft. Keogh, Montana, 1890. [Public domain photo]

The World War II veteran began talking about his early days in the army when they had him as part of a medical sanitation unit due to his background as a pre-med student. He noted some moments of difficult treatment he faced due to the color of his skin, which included having to move seats in a theater and sitting in a train car nearest to the engine room.

The first was during his time at the military base in Patrick Henry, Virginia and the second was while traveling with other soldiers to Fort Huachuca, Arizona. Despite the smoke blowing in the windows making him and his colleagues look “like walking bags of coal,” Caldwood was an optimist. “We didn’t care. We knew we were going to have a much better life,” the veteran said.

Caldwood recounted a humorous anecdote where he almost “missed the boat” figuratively and literally after he was hospitalized with diarrhea. The 92nd Division was approved for combat and was ready to be deployed. Considering he had joined the army to be a part of the Buffalo Soldiers, he was not going to miss this opportunity.

“I’m lying up in the hospital,” said Caldwood. “Uh-oh, I’m going to miss the boat. I took off! They wouldn’t discharge me, so I left. They said to me, ‘You have to pass, be fit to fight, in order to get on the boat…’ Oh, I passed it all right. I was in bad shape, but I made it.”

The Buffalo Soldier then delved into his experiences in Italy. One of the most poignant of his stories involved the Purple Heart Stretch. This was a road leading out of an Italian mountain village where the Germans would lie in wait to shell Allied forces with mortars. It was so nicknamed for the road’s penchant for resulting in the wounding or killing of many of these soldiers. Caldwood was leading some local women into town to buy some groceries, and to do so, he led them on foot down the Purple Heart Stretch. After finding the town devoid of supplies, Caldwood, the women and the other soldiers started to make their way back. That is where the story reached its crescendo.

“We get halfway back, and a mortar drops on us, everybody hits the ground…” Caldwood said. “When I thought that enough time had passed, they didn’t drop the second one on me, I raised up my head and I saw a partial wall not far from where we were… We got behind the wall, then 30 or 40 mortars came down… I said to myself, ‘They are not trying to kill us, they are telling us something.” The Germans were trying to tell them that “we’re not going to kill you guys. Instead, we are going to peacefully surrender to your platoon.”

The hero has a multitude of stories and a lifetime of lessons to teach the world and he is not done yet. He keeps himself spry and active and told the crowd on Thursday that he can do as many as 30 pushups. Those wishing to learn more about the “rule breaker and humanitarian” would be well-served to pick up Caldwood’s book, “Making the Right Moves.”

Dr. Janis Prince and Roy Caldwood at the St. Leo presentation.

Austyn Szempruch
Austyn Szempruch
Austyn Szempruch is a Graduate with Distinction, University of Florida College of Journalism and Communications. He's written numerous articles reporting on Florida Gators football, basketball, and soccer teams; the sports of rugby, basketball, professional baseball, hockey, and the NFL Draft. Prior to Hernando Sun he was a contributor to ESPN, Gainesville, FL and Gator Country Multimedia, Inc. in Gainesville, FL, and Stadium Gale.
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