Debbie Montgomery: A lifelong legacy of connecting her community

In a time where we’re grappling with issues of political polarization and police brutality, Miss Debbie Montgomery provides an example worth living by. Miss Debbie is one of the most respected people in the Rondo community of St. Paul, MN. She’s led an incredibly diverse career over the past 50 years. She has served as a police officer, city planner, youth detention lieutenant, Minnesota Assistant Commissioner of Public Safety, and teacher. Not only this, but she was also the first Black woman police sergeant in St. Paul. In addition, she was the first Black woman ever to serve on the St. Paul City Council. It should come as no surprise that Miss Debbie has left a legacy that her community will never forget.

Miss Debbie’s diverse résumé has an overarching theme: she’s a connector of people. When she speaks about her police work in interviews today, she emphasizes that law enforcement is a service profession, not a correctional profession. In every role, her first goal is always serving her community. Despite the immense impact she’s made, Miss Debbie remains selfless when reflecting on her career. To her, it isn’t about how she’ll be remembered. It’s about how she helped her community become a better place.

Growing up in Rondo: Lessons in community

Miss Debbie grew up in the Rondo community of St. Paul, MN, where she has lived her entire life. Throughout her childhood, she always felt her community was strongly invested in the well-being of others.

“If you needed something, your neighbors would share with you, and then you would reciprocate back,” Miss Debbie reflects.

She felt Rondo was specifically invested in the next generation, believing young people were the next generation of leaders. She was raised with forward-thinking values that encouraged everyone to push toward progress and inclusivity.

Having grown up in the 1950s, Miss Debbie remembers seeing some of the major issues on television. One issue in particular, African Americans’ voting rights, stuck out to her. In the early 1960s, there were significant barriers to African Americans’ ability to vote. Despite the 15th Amendment guaranteeing the right to vote, racist policies like Jim Crow laws created exploitative loopholes in many states. It never sat right with her that minority groups were most affected by these policies yet had no voice to demand change.

When she was 17, Miss Debbie decided to do something about it. In 1963, she got on a train to Alabama to participate in the March for Voting Rights. This march involved protesters walking from Selma to Montgomery, the state capital, to fight for African Americans’ voting rights. She remembers walking ten miles every day and sleeping by the side of the road at night.

The protests were a huge success, making a statement to the world and helping convince the government to enact the Voting Rights Act of 1965, which finally secured African Americans’ ability to vote by closing loopholes that had suppressed their voice.

During the same year, Miss Debbie was elected to the NAACP National Board. She worked with civil rights pioneers like Rory Wilkins, future Supreme Court Justice Thurgood Marshall, and Allie Mae Hampton.

These experiences cemented the importance of community advocacy. The connections she made and the lessons she learned shaped the direction of her career. She would go on to study Political Science at the University of Minnesota and earned a master’s degree in urban law and planning. Her dream was to work in a community-facing job where she could make a difference.

Answering the call: From city planner to officer

Miss Debbie had never intended to become a police officer. As a city planner for St. Paul, she was asked by the mayor to enroll in police training. At the time, St. Paul was reforming the department to increase African American representation. The city had mandated ten African American officers, and when one officer dropped out, they needed someone to fill the spot for two weeks. Little did Miss Debbie know, accepting this offer would change the trajectory of her career.

She excelled at police training, passing with flying colors and even tutoring other struggling officers. However, during her two weeks of training, a new mayor was elected and restructured city government, eliminating her city planner position. With no other choice, Miss Debbie remained on the force.

Though she initially had misgivings about being the first female officer on the force, she was determined to prove a woman could do the job as well as any man. She accepted the position and quickly showed her skill in handling difficult assignments. Her first call involved breaking up a wild party hosted by a notorious motorcycle gang, a probable attempt to test and intimidate her. She de-escalated the situation with remarkable communication skills.

One question guided her work: simply asking “why.”

“I finally started using some psychology on them and said, why are you all fighting?” Miss Debbie recounts. “It seems like you don’t know how to get help on whatever this problem was that started the fight.”

For Montgomery, policing was never about fear or punishment. She believes law enforcement should help those who stray while holding them accountable. Addressing root problems strengthens the community.

Breaking barriers in law enforcement

In 1987, Miss Debbie graduated from the Senior Police Management Institute at Harvard University and became the first Black female sergeant in St. Paul. Her ability to connect with others made her a natural leader. She used her city planner connections to refer people in need during calls and taught other officers to enforce the law with the same community-minded approach.

Later, she became a lieutenant in the juvenile unit, a personal highlight. She loved working with kids, teaching them to reflect on decisions, understand their values, and use their gifts. Many of the young people she guided credit her with helping them find better paths in life. Today, she occasionally runs into these kids, who tell her, “I haven’t gotten into any trouble lately, Miss Debbie.”

Serving Rondo in City Hall

In the late 1990s, Miss Debbie became Minnesota Assistant Commissioner of Public Safety, overseeing the state’s Public Safety department and shaping law enforcement strategies across Minnesota. She retired in 2003 but soon ran for City Council, encouraged by her community. In 2004, she became the first Black woman ever elected to the St. Paul City Council.

Her priorities on the council reflected the same focus on community connection: repairing the Jimmy Lee Community Center, supporting Black-owned businesses in Rondo, creating jobs, and expanding senior housing. She worked across political lines, showing council members why these were community issues, not partisan ones.

Advice for the next generation

Today, Miss Debbie reflects on her work at college courses and events, emphasizing the importance of knowing what you care about. In a world full of distractions, she encourages young people to focus on their strengths and passions. By understanding what they can contribute, they can authentically show up for their communities, cutting through the noise and making meaningful impact.

Alex Nellis is a recent Communication graduate who grew up in Saint Cloud, Minnesota.  He is passionate about social justice and has completed graduate certificates in gender studies and cultural diversity.