Category: Featured

The first time I met World War II veteran and Grand Hampton resident Roy Caldwood, his 101st birthday was being celebrated at Grace Episcopal Church in Tampa Palms (the church Roy and his daughter Diane Royer attend) in Aug. 2023. 

After that encounter, I told Roy I was excited to buy his book entitled Making The Right Moves: Rikers Island & NYC Corrections; Being Calm in the Storm about his harrowing experience as an assistant deputy warden who was held hostage during a riot at the notorious Rikers Island prison in his native New York City in 1972 (more than two decades after he completed his military service). 

I also said that the next time I interviewed Roy, I wanted to talk about not only the two Rikers Island riots he survived but also his experiences as a “Buffalo Soldier” during WWII. In fact, today Roy may be the last surviving member of that 92nd Infantry Division, which was the only Black regiment that saw combat during the war. 

I say “may be” because, according to the AI response I received during a Google search, the last surviving Buffalo Soldier was a man named Robert Dixon, who passed away in Nov. 2024 at the age of 103 — the same age Roy Caldwood is today. (So, for those of you who believe everything AI tells you, try doing some research on your own sometimes.) 

But, Roy is not only still very much alive, he is a vibrant man who can still do “probably 40” pushups (although he says 20-30 is his usual limit) and who loves recounting his stories of the Second World War and his century-plus-long lifetime of amazing stories. If you ever get the chance to meet him, ask him to tell you one story and you will end up being regaled by many tales of bravery, heroism and true evidence of why the members of the American military who fought in — and ultimately won —WWII have been dubbed “The Greatest Generation.” 

From Humble Beginnings 

Roy J. Caldwood was born in New York City on July 10, 1922. Although his parents never divorced, he says they were separated because his mother, a devout Christian, could not deal with his father’s gambling. 

“My father didn’t live very far from us,” Roy says. “He worked as an elevator operator and when I became a teenager and wanted to take a young lady on a date, I would visit my father at work and he’d give me a dollar. But I was raised without a father and the discipline that many of my buddies had growing up.” 

In fact, Roy says, when he was picked on by bullies at school — which happened a lot because he was small and slight — he had to run home to get his “sister” (actually a cousin that Roy’s mother raised) to help him fight his battles. “If I went home and got my sister,” he laughs, “those boys would be scared.” 

Eventually, a much larger classmate at the Parochial school he attended, “even though we weren’t Catholic,” took pity on him, “and taught me how to box. After a couple of lessons, I didn’t need my sister to fight my battles for me anymore.” 

He admits that the nuns at the Catholic school were the only ones who ever really disciplined him. “If our teacher left the room and came back, she’d ask, ‘Who was talking while I was out?’ and some of the kids would rat on each other,” which could cause them to get whacked on the knuckles by a ruler. “That was enough to keep me from getting out of line too often.” 

He also recalls an incident where, “I guess I did something bad. I don’t remember exactly what I did, but one thing I’ll never forget was that the nuns called for a bigger guy, an older student, and he picked me up and stuffed me in the dumbwaiter. I’ll never forget that. But, it was actually good for me. I learned how to control myself.” 

On To The Army 

After high school, Roy says he went to his draft board and mentioned that he was interested in medicine. “They put me in the Army, with 16 other Black guys, and said they were going to put us in a medical outpost or something, but they sent us to Camp Patrick Henry in Virginia and we formed a basketball team. And we were good. But then, I heard about this guy they called ‘Sweetwater’ Clifton, and I said, ‘We gotta this guy,’ so we drafted him and we played against colleges in the south…and beat the hell out of them.” (Note-Nat “Sweetwater” Clifton went on to become one of the first Black players in the then-fledgling NBA after serving in WWII from 1942-45.) 

When they weren’t shooting hoops, Roy says that all he and his basketball buddies did at Patrick Henry was kill mosquitoes, “and we all hated it. But then, I read an article in Stars & Stripes magazine that the 92nd Infantry Division was badly in need of more help, so I got two of my buddies to go with me and we were sent off to Fort Huachuca in (southeast) Arizona,” which was the base of operations for the Buffalo Soldiers of the 10th Regiment from 1913-33 and was home to 25,000 soldiers during WWII. 

“So, they put me and my two buddies in the medical unit and we had to pass a test to become Army medical/surgical technicians, and we all passed, no problem.” 

But then, Roy says he got diarrhea and ended up in the hospital. He says the Army was “breaking down Black combat outfits and making them into labor battalions. They had already done that with the only Black division that they had before — the 93rd — and they sent them to the Pacific. They were going to do the same thing with the 92nd, but the Black leaders fought them. So, they came to a compromise. They said, ‘We’ll allow one infantry unit to go to Italy and go into combat and see how they do. In the meantime, I’m in the hospital trying to get out, and they wouldn’t let me out, so I just left.” 

Roy says he went to the Day Room and spoke to the clerk there, who said, “Well, you have to pass the ‘Fit to Fight’ test, so you can qualify if the 92nd Infantry Division does go overseas.” 

But, even though he had just left the hospital, “I’m dragging, you know, but I still passed. The only problem was that they made my two buddies corporals, but not me. They made me a private.” 

Off To War 

So the 370 Regiment (which participated in the Allied assault on the Gothic Line, including the capture of Lucca, Italy, as part of the 92nd Infantry Division) did just fine in battle. 

“But, you read nothing about us in the American papers, while the European papers were full of news about the ‘Buffalos.’ But they said, ‘O.K., the rest of the 92nd division can go over.” 

In 1944, as the European campaign was winding down (Note – In Sept. 1943, Italy was no longer allied with Germany, after fascist dictator Benito Mussolini was ousted), Roy says he and the rest of the 92nd went in zigzag on a boat, “because the Germans were right there and, as we were approaching Italy, the boat tried to stop at one island, but they asked , ‘Do you have Blacks on board?’ They said, ‘Yes,’ so they said, ‘Well, then you can’t stop here.’” 

But then, the boat pulled up into Naples, where there were a lot of black longshoremen, “and oh, were they happy to see us,” Roy says. “They said, we are having a horrible time here because of the ‘Ugly Americans.’ The Italian longshoremen called White Americans ‘Ugly” because they looked down their noses at every other country. So, they were happy as hell to see us and they said, ‘We’ve been following you guys, so you won’t be having any problems anymore.’” 

After spending that one night in Naples, the 92nd proceeded on to Viareggio. 

“I think it was maybe the first morning, and I hear us firing our mortars,” Roy says. “I go outside and I see the lieutenant and the squad, and they’re practicing their mortars. They say, ‘If the Germans come, they can come two ways — over the mountain, and we have a platoon up there, and we’re protecting down below.’” 

Roy says he said to himself, “They should be warning the people where these mortars are falling. And then, I hear the sergeant say, ‘I think we hit one of their mules.’ I wanted to do something to warn the people in the village, but I can’t tell the lieutenant what to do. I’m just a medic. But, I can go warn these people myself. So, I said to the sergeant, ‘I am going over there to tell the people that we’re practicing our mortars and it’s a dangerous area, so they should take precautions — go in their houses and safeguard their animals.’ 

“The sergeant said to me, ‘You can go over there, but I am not going to stop firing the mortars.’ So, I said to him. ‘I’m going over there. You can keep on firing those mortars over there. But, if you don’t kill me, do not be here when I come back.’” 

He adds, “Then, the lieutenant says to me, ‘You don’t talk to my sergeant like that.’ I said, ‘OK, fine.’ But, I still went over there to warn them and came back and nobody said anything.” 

But then, over the next couple of days, one of the soldiers came to Roy and said he had a rash on his back. “I looked at it and said, “I’m sending you back to the rear. You need treatment. I can’t help you here [on the front lines]. 

“But, the lieutenant said, ‘Private, I don’t have enough soldiers up here now. You can’t send anybody back to the rear.’ 

“But, I didn’t pay him any attention,” Roy says. “I sent [the soldier] back to the rear anyway. I knew when he was supposed to be going out on patrol. And, when that day came, I picked up a rifle and took off my gear and I took his place. The lieutenant was surprised.

“But, that started it. From then on, any suggestion I made to the lieutenant, he’d say, ‘O.K.’ And yes, I made all kinds of suggestions.” 

For example, Roy got the lieutenant to agree to allow the soldiers to have a dance — “Even the lieutenant danced the night away — because I said I thought it would be a good idea for morale, and it was. That was the first of many ‘O.K.s’ I got from him.” 

The ‘Purple Heart Stretch’ 

As the American troops were moving through Viareggio, they were notified about a dangerous stretch of road known as the “Purple Heart Stretch.” 

“When we got into this village,” Roy says, “the lieutenant called for a meeting of the townspeople and told them, ‘You will not be allowed to leave this village for any reason whatsoever. Nobody leaves this village.’ And this guy, he’s like the mayor of the village, or whatever, says to the lieutenant, ‘We have not been able to buy food. I don’t know why. And we are all really getting hungry. We need food very badly.’ 

“But then, the lieutenant says, ‘I told you, nobody leaves!’ But, I’m always trying to solve problems and I’m thinking, ‘I gotta help these people,’ but what can I say? The captain already gave the lieutenant his orders — ‘Nobody leaves the village.’ So, what can I say?” 

So, Roy says to the lieutenant,“What if I escorted them myself, since I speak Italiano. And again, the lieutenant says, ‘O.K.’ So now, he’s defying his captain’s orders, and he’s gonna listen to a private — me — instead! 

“I said, ‘O.K., but I’ll have to take two volunteers with me. And right away, guys are saying, ‘I’ll go.’ I say ‘We leave in the morning.’ But, next morning. No stores. I know, great. That takes care of that. But, I hear a lot of noise — we were upstairs and there’s a lot of noise downstairs. And I say, ‘The women are there. My guys are there. I gotta be there. I cut downstairs and I said, let’s go. We’ll let the women lead the way. I didn’t want it to look like I’m walking behind these women’s skirts, so I let them walk way ahead. We weren’t walking very long when I looked where we were and I damn near fainted. I said, ‘We’re on the Purple Heart Stretch!’ 

“The Germans can look down from the mountain and see us. They can kill us right now. I gotta make a decision what the hell to do. I’m not gonna try to run out of there. I have to convince the Germans that we’re humanitarians — that we’re trying to help people who are starving. I gotta convince them. That’s my only hope. I’m gonna walk with my head straight up, like I don’t give a damn. Like I don’t care if I die. I said, ‘Let’s go’ to my two guys. It’s a good little walk but we get to the store. The women went in. And, when I went in, I saw the store was in complete blackness. I can’t see anything. I said, ‘There’s no getting any food in here. There’s nothing.’ So now, I walked the Purple Heart Stretch for no food, nothing.” 

He adds, “Now we gotta go back. So we started off. We got maybe a little more than halfway there and a mortar drops. Boom! So now, I’m lying in the mud there ‘cause they had rain. And I said, ‘It looks like I made a big mistake, but I’m not gonna be able to apologize to these people because I’m gonna be dead.’” 

But, Roy says he realized, “Germans don’t generally miss with their mortars — they’re very accurate. So, I’m lying there, waiting for the next one to finish me off, but nothing. So I raise my head up, I look around and I see a partial stone or cement wall and I said to my guys, ‘We’re gonna get behind that cement wall’ and I hollered to the group of women up ahead, ‘To the wall! To the wall!’ And they all get up and they start running and my guys are running. So then, I get up and I run. And, when I get behind the wall, the women had their prayer books and their Rosary beads out and they’re all just crying. 

“Just as I made it to the wall, the Germans increased the mortars. They must’ve thrown 30 or 40 of them, and they’re going ‘Boom, Boom, Boom!’ It looked like the more the women prayed, the worse it got. I said to myself, ‘Maybe I should tell them that it isn’t helping. Stop praying.’ But of course, I said nothing to them. 

“So then, I’m lying on the ground there, and the mortars are still dropping. And I said to myself, ‘Wait a minute. These mortars are not even falling close enough to kill us. They’re not trying to kill us. They’re talking to us! They’re telling me something.’ 

“So, I start trying to interpret the mortars. I figured out that the Germans are telling me that they figured out that I’m a humanitarian. I’m actually deciphering what this all means. It’s like they said, ‘We had decided earlier that we will fight to the death.’ But then they said, “Now, we’re not going to kill you.’ So, I said to everyone there, ‘They’re not gonna kill us. I am going to move outside very quickly. If I got it right, I’m alive. If I got it wrong, I’m dead.’ 

“So I moved outside, and I stood there. And suddenly, no mortars. That’s the God’s honest truth. So I said, ‘Let’s go back.’ And my guys and the women came out, and we all headed back.” 

Then, when Roy and his group went back, he says, “The lieutenant was standing outside up there waiting for me. When I met him, he told me, ‘The Germans sent a detachment to the village. They wanted to find out what the hell you were doing there — and our outpost saw them.’ 

“The men called the lieutenant and told him, ‘We see Germans coming into the village.’ The lieutenant called his captain who told him, ‘I want you to establish new quarters in the town.’ And, the lieutenant, said, ‘I can’t leave now because the doctor’s not here yet.’ So, the captain said to the lieutenant, ‘Don’t bother those Germans. Leave them completely alone.’ ‘Cause he knew if they did, me and my group were dead. The captain says, ‘When he gets back, then you reestablish.’ 

“So now, I’m back with the lieutenant and we’re hurrying to get to the new quarters down below. So, we get down below and we moved right in because we believed that the Germans were coming to peacefully surrender to us. So, we had to hurry.” 

The Surrender Of The Germans 

“So now, were back in the house, and we walk in the front room and one of our soldiers yells out to us, ‘The Germans are peacefully surrendering to us!’ So, he and I are running now to help with whatever. I see the lieutenant and the German soldiers lined up in twos, with no Americans standing guard over them. We don’t even have enough guys. They’re busy upstairs processing the other guys…the other Germans… that are still coming. It’s just one big, long line. And I can see what the Germans are saying. 

“They said, ‘We have to thank that man for what he is doing. He’s a humanitarian. He has saved our lives. We were going to fight to the death. But now, we are not fighting to the death anymore. We owe our lives to that man now, because we are going home and we are going to do humanitarian work, just like he’s doing.’ 

“It was like 40 or 50 German soldiers and we only had twelve. All we had was just one platoon. There may have been others behind us, but we didn’t know for sure. And, I don’t really know how many guys the Germans had, but they believed they were gonna die. They said, ‘We have him to thank. He has saved our lives.’ 

“So now, they’re all lined up and what I want to see now is the guy in charge who didn’t kill me. The one responsible for me still being alive. I just wanna see him. And, as I walk down the line looking, I hear some talking and I’m listening and there are two guys speaking English. And, you know what they’re saying? ‘There he is!’ A couple of times. I could look at them, I could even go over and shake hands with them. But, I said to everybody, ‘Right now, things are going a hundred percent. The Germans are cooperating. There’s nothing I could do now to make this situation any better. I could mess it up by saying or doing something wrong, but I’m not gonna do it.’ We didn’t even have enough guys to stand there and watch them. The lieutenant is saying, ‘I don’t have enough men,’ which was true. The captain knew he didn’t have enough men. So, the lieutenant called for an Italian civilian, a guy who helped us with our supply mules. ‘We need Joe,’ the lieutenant said. ‘I want Joe to escort these prisoners.’ 

“The Germans had plenty of men and ammunition. More American and allied forces for sure would have died if the Germans had decided to fight to the death. But, one or two days after that, the Army issued an announcement saying that, ‘The Italian campaign is over.’ 

On Celebrating The Army’s 250th 

On June 15, Roy posted on his Facebook page, “So grateful for being honored and invited to the 250th Army Anniversary Ball by Gen. Butler. An awesome evening of giving a toast, cutting the official Army cake and sitting in the Army war jeep behind the steering wheel.” 

He adds, “I had no idea how I would be received and my friend, General Butler, also said he had no idea. He said, ‘Roy, you’ve got so many people here!’ 

“It was great — Generals, their wives…All sitting at the same table! General Butler’s wife was sitting next to me.” 

Roy says if he never moved to Florida, he probably would never have met Gen. Butler. 

Diane agrees, although she also credits Viera with making the introduction. 

“Councilman Viera is who really made the connection. It was at least a year or two in the making. Luis kept saying, ‘Oh, Roy — I’ve got to connect you with the General. And it’s been a fantastic bond and relationship and like a love without them ever knowing each other before.” 

As to why the native New Yorker made the move to the Sunshine State, Roy says, “I ended up moving to Florida because my wife, Muriel, was very sick, and we moved in with my daughter, Diane. It was the best move I ever made.” 

Diane adds, “They were being considerate of my husband (Donald) and myself, because we moved to Tampa in 2001 and we were having to travel back to New York every time to check on them, even though they were very independent. And then came the pandemic. They decided to move here at the end of 2020 for our sake.” 

In our Aug. 19 New Tampa issue, I’ll tell you about Roy’s 21-year career in corrections, including his book about being held hostage on Rikers Island. Thank you, Roy & Diane!