Brad Dudding , Feedback Labs | May 20, 2025
Too often, people entangled in the criminal justice system feel unheard, stigmatized, and dehumanized. At The Bail Project, real justice starts with listening. On June 5, The Bail Project will share lessons from its work on the Flathead Reservation in northwestern Montana at the Feedback + Bozman Summit. Our session, “Listening for Justice: How Empathy Shapes Pretrial Reform on the Flathead Reservation,” will explore how trust, cultural humility, and deep listening shape a more compassionate and effective approach to pretrial justice.
For millions of Americans arrested each year, pretrial freedom depends not on community safety, but on the ability to afford cash bail. This system is both unjust and unsafe. Those who can’t afford bail often endure the harsh consequences of incarceration – losing their jobs, housing, and connection to their families.
The Bail Project intervenes in this cycle of poverty, incarceration, and punishment to provide free bail assistance and pretrial support to thousands of low-income people every year, while advancing policy change at the local, state, and national level. Our model challenges the notion that cash bail is necessary to ensure court appearances, as our clients return to court 92% of the time without money on the line.
Nowhere is the inequity of pretrial systems more visible than in Native American communities. On the Flathead Reservation – home to the Confederated Salish and Kootenai Tribes – historical trauma runs deep. This land, once part of a much larger sovereign territory, became one of many reservations in Montana subject to forced allotment, fracturing Tribal landholdings and dispossessing Native families of their homes and resources. Later, government-run boarding schools separated children from their families and cultures, inflicting cycles of harm that continue today.
In Montana, Native Americans make up just 6% of the population, yet they account for 21% of the state’s male prison population and 37% of the female prison population. This disparity is even more pronounced in county jails, where pretrial detention disproportionately affects Native American clients. On the Flathead Reservation, The Bail Project has seen firsthand how these systems of punishment collide with histories of violence and neglect.
However, progress is happening through partnership and people-centered solutions.
The Tribal Defenders Office of the Confederated Salish and Kootenai Tribes plays a vital role in this transformation. Their holistic defense model extends beyond legal representation, providing comprehensive support that addresses clients’ social, emotional, and cultural needs. From mental health referrals to connections with cultural resources, the Tribal Defenders ensure that people are not only defended but deeply supported throughout the pretrial process.
Together, the Tribal Defenders and The Bail Project are working to provide clients with the opportunity to adjudicate their cases from a position of freedom and access resources to heal and stabilize their lives. This collaboration redefines what pretrial justice can look like when built on listening, trust, and community care.
Two of the most powerful voices in this story belong to Jean-Paul and LaVonda, members of the Confederated Salish and Kootenai Tribes, who were bailed out by The Bail Project and supported by local Bail Disruptor Riley Pavelich and Josh Cahoon, the Lead Case Manager in the Tribal Defenders Office.
Jean-Paul is a member of the Confederated Salish and Kootenai Tribe (CSKT) and has spent most of his life on the Flathead Reservation. “Certainly, I never envisioned myself being put in jail for anything,” he said. “I’ve never had any run-ins or encounters with police other than traffic stops.” His connection to his home is rooted in family, tradition, and stability—something he was fighting to maintain.
LaVonda is also a CSKT member grounded by her deep commitment to sobriety and healing. “This land is where I started over,” she said. “I’ve worked hard to stay grounded here.” She speaks with fierce honesty about her journey, including the pain she carried during active addiction: “I asked my son, ‘Please don’t ask me to stop getting high. That’s the only thing that’s getting me through life.’”
Both Jean-Paul and LaVonda navigated intense personal challenges before coming into contact with the justice system—challenges that reflect larger systemic barriers faced by Native American communities: limited access to healthcare, cycles of intergenerational trauma, and a legal system that too often criminalizes addiction and mental illness.
LaVonda, despite over 500 days of sobriety and steady employment, was jailed for driving without a license and again the next day for a nonviolent offense that occurred 4 years previous. “I never thought I’d go to jail sober,” she said. “I feel like I did a lot of time because I was an addict.”
For Jean-Paul, a brief relapse after eight months of sobriety led to his arrest. Though he had no prior criminal record, he was booked into jail, and within 24 hours, his serious medical condition became a crisis. Without access to essential medications, he had to be transported to the hospital for emergency stabilization. “I couldn’t believe that I was going to potentially face years in prison,” he said.
When The Bail Project learned of their cases, we stepped in. For Jean-Paul, we posted bail, allowing him to return home and access urgent care. He later completed substance use treatment on his own and has remained sober ever since. “If it weren’t for The Bail Project and for Riley, I don’t know how long I would have been in for,” Jean-Paul said. “Riley was very, very thoughtful, caring, and very helpful.”
For LaVonda, Riley ensured she was released quickly. “She’s there when I have to go make my court appearances,” LaVonda said. “I don’t really have faith in people. With Riley, I always thought it was genuine.”
Riley sees this work not just as case management, but as care. “It’s just important to hear people where they’re at,” she said. “It’s so much more than just listing out the charges… It’s about hearing where they’re at in their life, where they’re at emotionally, where they’re at mentally.”
She added: “The listening model gives you so much more context for people’s situations and lives. When you hear the underlying stories, it’s just so obvious that those people need help.”
Since their release, both Jean-Paul and LaVonda have continued their journeys of healing. Jean-Paul has maintained his sobriety and reconnected with his family and community. LaVonda continues to meet her obligations through the Tribal Healing Court, attends Narcotics Anonymous meetings, and holds down a job she’s had for over two years. “The Bail Project is really cool because it takes people who don’t have the means to bond out. But that doesn’t mean they don’t need to get out because of their children and jobs,” she said.
What happened to Jean-Paul and LaVonda is not unique. It reflects a system that too often prioritizes punishment over support, and money over safety. Their stories highlight the urgent need for pretrial systems that recognize people’s full humanity—and for models that listen before they judge.
Join us in Bozeman as we hear more from Jean-Paul and LaVonda, exploring what it means to truly listen for justice and how empathy, partnership, and culturally grounded care can help reshape the future of pretrial reform, starting with the Flathead Reservation.
As the Chief Impact Officer, Mr. Dudding oversees the nexus of program operations and evaluation and has helped the organization scale its work nationwide. Prior to joining The Bail Project, Mr. Dudding held several senior positions, including Chief Financial Officer, Chief Operating Officer, and Chief Impact Officer at the Center for Employment Opportunities, a nonprofit headquartered in New York City that provides employment services to individuals who have recently returned home from incarceration. In his over two decades at the Center for Employment Opportunities, Mr. Dudding helped the organization build capacity to expand nationally and deliver results for its participants. Mr. Dudding received a B.A. in economics from Macalester College, University of Missouri and a Master of Urban and Regional Planning degree from Rutgers University.
