Two years before Dr. Martin Luther King Jr. delivered his “I Have a Dream” speech in Washington, 15-year-old Debbie Montgomery was boarding a train for New York.
She travelled on her grandfather’s railroad pass, moving from car to car as porters watched over her. Strangers made sure she had a seat, a meal in the dining car and a sense of care that stretched all the way to the East Coast.
“This is Gil’s daughter,” they told one another, handing her off from Minnesota to Chicago to New York so she could attend her first National Association for the Advancement of Colored People (NAACP) conference.
When she arrived, she found herself face-to-face with teenagers from the South.
“I was with all of these Southern kids that are experiencing things I only see on TV,” said Montgomery, who grew up in St. Paul’s Rondo neighborhood. “I learned a lot about the civil rights movement from what the kids were seeing or hearing from their parents, and I’d come back home and tell the kids back here about what was going down in Alabama and Mississippi, and all these different places.”
Sitting at the table of giants
By the time Montgomery was 17, she was the youngest member on the NAACP’s national board — a seat usually reserved for college students.
“I had become so engaged in the movement that the youth all got together from all of these different states and said, ‘We want you to be our representative,’” she said.
Suddenly, Montgomery was sitting at the same table with Supreme Court Justice Thurgood Marshall, civil rights leader Roy Wilkins and activist attorney Margaret Bush Wilson. For six years, through two terms, she carried the voice of Minnesota youth to national meetings.
“It was so interesting to hear the conversations that went on at the national board with these powerful leaders,” she said. “Here I am from Minnesota, raising my hand asking, ‘Why? Why aren’t we doing this and why aren’t we doing that?’ And I know they were tired, but they were engaged, and I was willing to speak up.”
Though Montgomery was growing into a leader of her own, nothing had prepared her for the historic speech at the steps of the Lincoln Memorial. Knowing Dr. King primarily as a minister, she expected to hear a sermon.
“But when he got to that ‘I Have a Dream,’ I mean, it just flowed,” she said. “Everyone could just feel it. All of that exuberance was coming out. You just felt, ‘God, this is powerful. He’s telling us a story and giving us marching orders on things that we need to do. It was just so visionary at the time.”
In 1965, Montgomery and fellow University of Minnesota students joined the 52-mile trek from Selma to Montgomery, Ala., in demand for voting rights.
“The marching was one thing,” she said. “But then you went to the board meeting with Thurgood Marshall. They were looking at the legal aspects and how we, as an organization, were going to approach the Supreme Court. I was just so blessed to hear that.”
Diversifying St. Paul’s Police Academy
Montgomery’s early activism provided the foundation for her academic pursuits. She earned a bachelor’s degree in political science and a master’s degree in urban planning and urban law, becoming one of the first African American graduates of the University of Minnesota’s Humphrey School of Public Affairs. In 1980, she was also among the first two African American graduates of the Master’s in Public Safety and Law Enforcement Program at the University of St. Thomas.
Today, at age 79, she continues her education through classes at St. Thomas’ Selim Center for Lifelong Learning.
In the early 1970s, Montgomery was working as a city planner for St. Paul Mayor Lawrence Cohen. At the time, the city was under federal pressure to diversify its police force due to a 1971 NAACP lawsuit. Cohen asked her to take the police exam, not necessarily to become a cop, but to demonstrate that there were qualified women and minority candidates in the testing pool.
She passed the West Point physical agility test — the only woman out of hundreds of applicants to do so at that time. She initially declined to enroll in the academy because it meant a pay cut from her planning job.
But when one of the Black candidates dropped out just days before the academy was to start, Cohen called Montgomery again. He asked her to sit in temporarily because the academy couldn’t legally start without enough Black candidates.
Her first assignment placed her alone in a squad car on Rice Street, working midnights in an area with 42 bars.
“At that time, it was the highest crime area,” she said. “I’d get called to a bar fight and I’m waiting to hear on the radio if somebody’s coming to back me up. I’m all of 127 pounds, trying to break up a fight, and my troops aren’t coming, and then after a while, they come when they figured that I was getting my butt kicked.”
When she eventually rose to lieutenant of the juvenile unit, she drew on her training in urban planning to reshape policing. She made sure officers weren’t just writing tickets but connecting the youth to resources. Even as a senior commander, she prioritized de-escalation over arrest.
“I hand-picked my investigators — people that I felt had some compassion and empathy and that could work with young people,” she said. “Everybody had to have a list of all the nonprofits and social service agencies in their area. If they made a referral, it was to a real person who could help.”
It was the same ethic Montgomery had carried since her teenage years in the civil rights movement — the belief that justice required both accountability and care.
Tapes of a dreamer
More than 60 years later, Montgomery still keeps tapes of Dr. King’s speeches in her bedroom, listening to them to find clarity in a modern world that feels increasingly divided. To her, the “dream” was a blueprint for a country that she fears is now losing its way.
“Now I look today, and we aren’t talking to each other,” she said. “You’ve got the left, you’ve got the right. Where are the people in the middle trying to help us pull this together and move forward as a country? This is decimating us with this friction that’s going on.”
“I can’t tell you how many people call and say, ‘Debbie, what do we do about this?’ And I’m thinking, isn’t there anybody else that’s working on these issues?” she added. “I’m honored that they respect me enough to call me, but where are the young people? I’m always waiting for young people to rise up. I just haven’t seen that movement like we had back in the ’60s and ’70s.”
Montgomery’s hope is that today’s youth lean on one another to build a sustainable, collective power in the fight for human rights — know yourself, then find your tribe.
“Be honest with yourself and decide, what is your strength? What strength do you feel God gave you? Now after you’ve been honest with yourself, identify someone that’s strong in your weaknesses,” she said. “If each one of us can uplift each other in our weaknesses, we’d all have a better understanding of how to make society better for everybody.”
While the world has changed since she first boarded that train to New York, she warns that the struggle has simply evolved.
“Our environment, as African Americans, is much better today than it was then. It’s just not as violent, but it’s all under the table,” she said. “That’s the reason I still come to school. I want to learn how I can continue carrying out my purpose.”
