A Tale of Two Brothers

“The conversations were great and I think that’s where I got my knowing there’s two sides to every story. And I’ve carried that up through my kids and my grandkids.” 1 David Caldwell Jr.

Since the time of the founding of UNC, the nation’s first public university, Caldwells have lived in Chapel Hill: white Caldwells and black Caldwells, initially bound together through the institution of slavery. The white Caldwell family owned much of the land on which UNC’s sprawling main campus now sits; the enslaved Caldwells helped to build and maintain the university.

After the Civil War, many of the newly emancipated Caldwells stayed on to serve UNC’s white, male presidents, students, and professors. These Caldwells moved to the surrounding area and many ended up, along with other descendants of slaves, building their own houses in the Northside neighborhoods in segregated Chapel Hill.

My interviews with Mr. David Caldwell Jr., whose grandparents moved to Northside from nearby Chatham County, began with a few photographs.

The cover of Jim Wallace’s Courage in the Moment, a collection of images from the civil rights movement in Chapel Hill in the early 60s, features a tall black man leading a protest march past a white police officer. Other pictures in the book feature another tall black man, a police officer on the scene to patrol the protests.

It turns out, these men were brothers. One of them was David Caldwell Sr., one of the first black policemen in Chapel Hill. The other was his brother, Hilliard Caldwell, who is widely credited with organizing many of Chapel Hill’s civil rights marches and smoothing the way to integration at Chapel Hill High.

How could you not want to know what Caldwell family get-togethers were like? I sure did, and David Caldwell Jr. was kind enough to sit down and answer my questions:

Mr. David Caldwell Jr.: “It always made things very interesting for family gatherings …with my father being on one side and Hill on the other. And I don’t think you’ll see my father arresting anyone in these pictures but he was there as far as helping people. The comment was made that when he had one of them, that he only stood up against the wall and did not participate….”

Me: “How did he get away with that?”

DC: “He just didn’t do it. … He showed up and did everything but what they’re doing.”2 [He points to a picture of police officers hauling demonstrators to be arrested.]

David Caldwell Sr. did not pull out a baton or drag demonstrators into paddy wagons, though he did assist with carrying some. The story is different for his colleagues. Often white officers attempted to humiliate demonstrators not just by using unnecessary force but also by crossing boundaries, for example, when officers arrested Euyvonne Cotton, she remembers, the white officer reached under her dress.3 This would have been unthinkable to an officer like David Sr. In another photo he can be seen gently reaching his arm behind a young black kid taking a photo of policemen arresting protestors, a gesture that appears protective. He was a presence—watching, but also watching out.

And he was being watched, tested by his fellow officers. His self-respect was on the line whenever he went to work, and his dignity had to be sacrificed more than once. In David Jr.’s words, “Dignity was good but it didn’t put food on the table. So you had to do a lot. You had to eat a lot of straw to just make sure things didn’t go wrong.” For David Jr. and his three brothers, that meant not getting involved in marches, demonstrations, or riots.

His father’s influence, however, did get him out of a few difficult situations, usually when he was in the wrong place at the wrong time. Like the time he and his buddies were crossing campus after dark when the police were answering a sexual assault call and stopped to question them. Or the time David Jr. was pulled into a student demonstration at Chapel Hill High and was handed a rock to hold. On these occasions, he felt the relief that came from his father’s hard-earned respect in the larger community. Once police recognized “Big Dave’s” son, they eased up on him. But David Jr. knew he wasn’t off the hook just because the cops stopped questioning him. He feared the thought of coming home and having to answer to his dad.

So, what really happened at those Caldwell family gatherings? Here’s how David Jr. tells it: “You just kind of sat back and listened to their discussions. And they would talk about things that weren’t right and things that weren’t done and … they had always been a hard working group. They all had two, three jobs at one time. And to talk about things they would, you could hear them go through on their jobs, was just amazing to me, to listen and say, okay so this is—I didn’t know what it was called then. I knew it wasn’t right. … It was racism.”

He told me about how his father took him to Black law enforcement conventions where he heard stories of injustices they suffered on the job. He saw his father address young white men with, “Sir.” But he also told me about how, later on, when his father owned a garbage collection business, he would pay for his trucks in cash, stunning the condescending white salespeople who assumed they would need to work out a considerable loan. These were the small triumphs, but they clearly made an impression on young David.

And he told me about how his uncle Hilliard, who worked as a truant officer, faced similar challenges and dangers. Hilliard realized that truancy was often linked to poverty. He made house calls and found that kids often stayed home because they didn’t have a shirt, shoes, or money for lunch. I had heard that in the early 70s, Hilliard had been a sort of liaison between protesting students and resistant faculty at newly integrated Chapel Hill High, and so I assumed he had somehow earned the trust of both sides. As David Jr. put it: “I’m not going to say that that administration had any trust in him. This is my opinion. Because the people that were there were put there because they had to be put there. They didn’t want them. I’d be surprised if you could find anybody there that could say, ‘This administration wanted us there.’”

No doubt, David Jr. learned some memorable social studies and civics lessons by listening to the older generation talk. One thing he remembered is that no matter where they worked, they always had stories of prejudice and the frustration that comes with having to swallow “straw.”

Initially, when I asked about the differences between his father and uncle’s responses to the protests, David Jr.’s answer surprised me: “It didn’t affect the chemistry of the family at all. I mean, it was just like sitting down and talking about football. It did not affect anything. We just, you know, sat and listened and learned. It made it easier for us to identify, to think on our feet when things were going down.”

And things were definitely going down. The pictures featuring his father and uncle were taken during the numerous demonstrations, protest marches, and sit-ins of the early 60s. David Jr. describes his experiences with race at the time: “The town was very divided. I loved growing up and seeing so many Black people. It was unbelievable up on Graham Street and Merritt Mill Road and the black businesses and the Black theater, Black stores. You know it was just a huge deal. And you had a line that you didn’t cross, that was understood. We had a time limit that when that time came you needed to be back on that side of town. And I was just young but I was old enough to see it and recognize it, that something wasn’t right.” After the inaugural wave of protests in the first years of the 60s, the town was forced by the Civil Rights Act of 1964 to desegregate businesses. The daily fight to desegregate schools, however, continued. Despite the 1954 Brown v. Board of Education Supreme Court ruling, the state and the town had decided to implement the ruling gradually—very gradually. In 1959, the parents of 12-year-old Stanley Vickers sued the school district after their request for a transfer from Northside to nearby Carrboro Elementary was denied.4 After three years of litigation, the Vickers finally won the case and Black students won the right to attend all-white schools in Chapel Hill. School transfers began in 1963.

Prior to actual integration, David Jr. was one of the first Black students to enroll in Guy B. Phillips Junior High School. At Phillips he was forced to apply strategies he had picked up from those dinner table conversations. “I went to Guy B. Phillips. And seeing and dealing with teachers who didn’t want to teach you, students that didn’t want you there. I remember going and feeling like so many times, you know, ‘God, what did I do wrong? … Why are they making me go here and making me go through this every day?’ And you know, it was almost like, we have to pay this bill. And this is how you pay it, for everybody to benefit from it. I remember being hit in the back of the head, pushed down the steps. The teacher asked me one time, what I was fighting for? And I said, ‘Well, he pushed me. He called me a nigger and pushed me down the steps.’ He said, ‘Well, son, you are a nigger.’”

A few years later David Jr. would be part of one of the first integrated graduating classes at Chapel Hill High. He was in school on the day the Governor called in the troops to deal with students threatening to riot. It just so happened that the man called in to manage the crisis was David’s uncle Hilliard. In an October 2020 interview, Hilliard explained the events of two tense days in 1969:

“If any kids brought problems to me I would take them to the administration at that time to try and work it out. I served as a mediator between a student and a faculty member if there was a problem. Again, this is two years after integration and things were still not right there. I’ll never forget when the governor at that time was Terry Sanford sent about twenty-five state highway patrol, which was under his command to the high school as a result of somebody calling his office and saying that there was going to be some turmoil at our high school. I will never forget coming to work that morning and as I pulled off of Homestead Road into the lot and saw all these highway patrol cars sitting out there and said what in the world is going on? Of course, there was turmoil throughout the South going on at that time too. Somebody had got to the Governor’s office and said there was going to be some problems that day. Of course, our job was to try to maintain calm as best we know how. The kids did get rowdy after about the second class. I’ll never forget that morning. I spent thirty minutes convincing Black kids to go on to class. They tore out ceilings and broke off—they did some damage. I finally said, ‘If you keep this up and I can’t control the white administrator here. If she gets on the phone and if she calls 911 and tells them she needs help in this building those guys sitting out in those cars—they were all redneck whites—they are not going to take pity’s sake on you. They are riot ready with helmets, with black sticks or nightsticks and if they have to use them they will use them, and you don’t want that to happen.’ We were successful in calming them down. I told the two principals that you’ve got to tell these kids that you will sit down and talk about the inequity, as they exist in this building.“5

His hard-fought respect as a community leader, as well as his experience working with administrators, put Hilliard in a position not unlike the one his brother was in when, as a policeman, he was faced with deescalating confrontations between officers and protestors. Interestingly, David Sr. had also been on the scene at the high school that day. After making sure his sons knew not to be near any of the confrontations, he dropped off David Jr. and his brother Larry. David told me, “[T]here were cops out in front and everything and they were all white and they knew him. And he explained (…), I don’t want anything happening to them. And they were, ‘Yes Sir, oh yes, nothing will happen.’”6

Both Hilliard and David Sr. had earned respect from white town leaders, but they knew how fine a line they had to walk. The younger ones learned to respect that line. For example, David Jr. remembers that he had clear orders from the legendary football coach, William Peerman, not to get involved in the protest efforts so as not to risk being denied a college scholarship. Despite sharing some of the anger students were expressing towards administrators, he listened to his coach. He undoubtedly felt much of the inner conflict his uncle felt as tensions rose, and he must have heard the voice of his father in his head as well. Both of the younger Caldwells chose to stay out of the heat.

David Jr. ended up getting numerous scholarship offers, and after graduating in 1972, played ball for the historically Black university North Carolina Central, an accomplishment that made his coach, his father, his uncle, and most everyone else in the Northside neighborhoods proud. Accomplishments never went unnoticed, especially when your name was Caldwell.

When faced with the same sort of situations his dad and uncle talked about at family get-togethers, David Jr. learned about different ways to get along in segregated, deeply prejudiced, hostile, and sometimes violent Chapel Hill, different strategies for the daily fight. But he also learned to listen to all sides before making a decision, that there is something to learn by considering different viewpoints. In this way, he seems to have taken lessons from both his father and his uncle. And looking back over his rich life so far, it’s possible to see the influence of both: like his father, he has served his country as well as his town and county as a police officer, and like his uncle Hilliard, he’s been a tireless activist for social and environmental justice.

Interestingly, it was a memory of his father’s—the law enforcer—that ignited David Jr.’s political activism. Whenever he is interviewed about his role in a campaign against a hazardous landfill in the Rogers Road neighborhood, David Jr. tells how the struggle began with a promise made by the town in his father’s presence—a promise that went unfulfilled for more than four decades. In 1972, Howard Lee, Chapel Hill’s first and only African American mayor, together with members of the town council, signed a contract in the Caldwell’s backyard stating that when the landfill was shut down in 1985, the town would build a park and recreational area in the neighborhood. Believing that trust was good but a contract was better, David Sr. made sure his sons witnessed the signing. David remembers: “My father told me and my three brothers that this was going to be a really good thing for us, especially since the contract promised we would get a basketball court and ball field.”7 When the town decided to expand rather than shut down the unlined landfill, David Jr., then a policeman like his dad, began organizing neighbors. Without a doubt, that’s what his father would have expected him to do, since, as his son put it, “my dad believed that a contract, just like an officer’s oath, wasn’t something a man would break.”8

Within the Northside community it was known and went without saying that the outside world defined everyone—whether cop or protestor—first and foremost by skin color. Everyone gathered around the Caldwell family table would have known how that felt. In an atmosphere of trust and safety, they shared their stories, leaving David Jr. and the other young Caldwells to hear and feel the mutual understanding among them rather than the lesser disagreements. The young David must have realized that his elders were able to make inroads and bring about change one step at a time in different contexts—police procedures, school district policies—for example by working hard, showing self-restraint and self-respect, and forming alliances. When facing discrimination himself, David Jr. has had to be patient, but decades later he remains determined to work for justice. Not joining the struggle has never been an option. That theme runs through every conversation we’ve had since I first met him in 2015.

As the younger Caldwells faced prejudice and discrimination in their white-majority schools and town, they knew they were often, as David Jr. puts it, “up against an army.” But not without an arsenal of family-tested survival strategies.

One of the many things I learned from David Jr. is how to better read the photographs from the 60s, which I used to see through the lens of police vs. protestors. In those pictures his father is not just playing the part of the cop; he is fighting his own battle for respect, for a decent income, and for the future of his family and community. And Hilliard, as a truant officer in the schools, also faced off daily with those who did not want him or the kids he cared about to be there. One chose to work within an institution, guardedly; one chose to work at the edges of an institution, diplomatically, while also directly confronting the institution that employed his brother. There was not one universal approach to the crisis of their moment, and there were far more than two neatly delineated stances.

Occupying different positions, David Sr. and Hilliard faced constant obstacles and suffered ongoing humiliations, but they also talked to each other in a common language shaped by community values. As Hilliard put it, “You obeyed your parents; you obeyed everyone in the community, the adults in the community, and everyone in the church. … [T]he next-door neighbor had just as much power over me as my mom did.”9 David Sr. likely would have nodded in agreement. In the Northside community, every child was held to more or less the same standard by more or less every adult. “My mom used to say to carry yourself—I will never forget this and it took me years to understand it—she would say to carry yourself so that when you walk down the street as an adult, people can say there goes one of Irene Caldwell’s sons.”10 No son of Ms. Irene, it seems, failed to meet her “community first” standards. From everything I’ve heard, she would have been equally proud of both of them, since they both earned the respect of the community that willingly shared the responsibility of raising them.

Though the photos depict two sides at odds with each other, what one can’t see is that the Caldwells had more that held them together, more that they agreed on than disagreed on. Compared to the crippling affront of racism, differing strategies for advancing personal and community goals—whether with or in resistance to the powers-that-be—was not a deal breaker by any stretch. As Black men in a town divided by race, the Caldwell brothers shared the same roots, the same neighborhood, the same day-to-day challenges … and a bond that continues to inspire successive generations.