From behind bars to the Bar
I was a bit skeptical before this interview. No doubt many a reader would be. Why would anyone teach a prisoner how to defend themselves in court?
The premise — that prisoners and prison staff in Kenya and Uganda could be trained as paralegals and lawyers to defend themselves and others — struck me, at first, as too well-meaning. Likely just a pipe dream. But then what do I know about the justice system in Kenya, Uganda, and possibly other African nations?
To me this was the kind of idea that sounds beautiful on paper and quietly falls apart on contact with reality. But here is what Justice Defenders works with: overcrowded prisons, under-resourced courts, colonial-era legal systems creaking under their own weight. Getting an attorney to defend your innocence for free comes at the expense of time. You could wait years for a plea bargain, if that was even an option. Reading a law textbook in your cell could actually save you, if you were wrongly incarcerated in Kenya or Uganda.
Matteo Cassini, Director of Fundraising at Justice Defenders, did not take offense at the initial skepticism. He welcomed it.
“We believe that certain things can only be seen through eyes that have cried.”
Those words really stood out, as there could be nothing more authentic in the pursuit of justice than the passion of someone who wanted to correct the system after falling through the cracks.
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For almost twenty years, Justice Defenders has in fact worked to equip and empower people within prisons to become paralegals and lawyers. They train both incarcerated individuals and prison staff.
The organization operates 22 legal offices inside prisons across Kenya and Uganda, where they host weekly legal education sessions and keep their doors open for prisoners to draw on help from their trained peers. Currently, more than 250 paralegals are active, each receiving a stipend for their efforts. Unlike charities that simply send in outside lawyers, Justice Defenders focuses on building legal expertise from within the prison community. It works well.
As Cassini explained, the rationale is both philosophical and practical:
“Those who have that lived experience of incarceration add something that no lawyer who has studied through law school alone can have — that first-hand understanding of what injustice looks like, of what struggling to have your day in court looks like.”
Before speaking to Cassini about the work of Justice Defenders, my insight was limited on the scope of the problem they are trying to solve. A significant proportion of the prison population in both Kenya and Uganda are on remand — held before trial, and sometimes for years, without having been found guilty. Cassini put it plainly: there are around 25,000 people in Kenya and a similar number in Uganda who are held on remand, some for up to 10 years without conviction, without seeing their day in court, without receiving legal information. Legal systems shaped by historical structures, ongoing resource constraints, and systemic bottlenecks mean that due process is often a luxury afforded to few.
Wrongful convictions and endless delays are destined to occur within systems facing structural constraints.
The most powerful proof of what Justice Defenders does is Morris Kaberia , who spent 13 years in prison for a crime he did not commit. He was framed by his former boss and, without access to a capable lawyer, was sentenced to death for robbery with violence. Inside, he joined a nascent program where prisoners and prison officers were invited to study law together in the prison library.
Initially reluctant, he became one of its first participants. Skepticism is all around us, although Kaberia’s hesitance came from a traumatic situation only he could understand. Once in the program, he learned the law, worked with colleagues on his own appeal, and in 2018 argued his own case in front of the court. He was released on acquittal, his wrongful conviction recognized and overturned.
As of this writing, Kaberia is about to be admitted as an advocate of the High Court of Kenya and serves as Director of Legal Education at Justice Defenders — leading the very program he once studied while incarcerated. As Cassini put it, Kaberia went “from the bars to the Bar.”
Defending justice jointly
Justice Defenders is careful about how it positions itself within the legal ecosystem. Rather than publicly criticizing judges or government officials, the organization collaborates. Cassini was emphatic on this point:
“We’re not adversarial. We exist to strengthen the rule of law in the countries we’re in. We work with the institutions and within the institutions — and we invite those who hold power, the judges, the magistrates, the lawyers, to come and hold hands and to learn from each other.”
Everyone qualifies for their services, as long as they lack access to legal representation.
Justice Defenders does not screen clients by the severity or nature of their alleged offence. When pressed on this — on the discomfort of potentially assisting someone who has done genuine harm — Matteo was clear:
“We don’t ask what brought them to prison. We believe that we all are more than the worst thing we’ve done — or that we’ve allegedly done. Anyone who has the willingness and the desire to serve is welcome.”
The values filter of integrity, solidarity, bravery, excellence, and humility applies to those who work within the organization, not to those seeking help.
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The other part of this interview focused on fundraising. How does an organization like Justice Defenders sustain itself? Grassroots and community-driven organizations are often told that authentic impact will attract resources.
That is true, up to a point. But good work alone does not attract funding. These kinds of resources have to be cultivated, often over years, through relationships that go far beyond grant applications. Years of working on clout, visibility, and community participation are all part and parcel of the pain of fundraising for NGOs.
Justice Defenders relies primarily on philanthropy — trusts, foundations, and high-net-worth individuals, largely based in the United States. It actively avoids the quick payoff, and Cassini’s framing of this approach is worth sitting with:
“The work that we do is only possible because of the relationship and the trust that we’ve built over the past 20 years. Just showing up day in and day out, showing that we’re not here for a quick buck, that we’re here for the long run. We’re not transactional in that sense. And I guess it’s quite refreshing for a number of donors.”
Still, impact metrics matter: Justice Defenders has worked on over 170,000 cases and supported the release of over 70,000 people. But Cassini was candid that numbers alone do not move people. Stories do. They use storytelling and media like CNN, Anderson Cooper, and 60 Minutes to create the conditions for those relationships to form.
For organizations just starting out, his advice was grounding in its simplicity. Do not start with marketing. Start smaller than you think you need to:
“It can begin — it has to begin — in the smallest fashion, just serving the one that is in front of you, and then getting to understand the community that that one person is coming from, fully, deeply, immersing yourself.”
And on the temptation to lead with branding:
“Surely there are ways of starting this work from a more marketing perspective — you come up with nice photos and nice slogans, and you put something out on the internet. But I don’t know if that’s sustainable. I don’t know if you can do that type of work with full integrity.”
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Symmetry in New York
Justice Defenders is now expanding to the United States, with a pilot in New York State launching this year. It will begin with an introductory course in law, develop into an accredited paralegal training program, and aims before long to offer a full law degree to participants. The same pathway established in Kenya and Uganda, replicated inside American prisons.
On the ground, Bruce Bryan, incarcerated in New York for 29 years, drives the program. He watched the 2021 60 episode of Minutes on Justice Defenders from his prison cell, put the JD on his vision board, and began writing letters. Cassini replied to one of them while Bruce was still inside. A year later, Bruce received clemency. Today, he drives the New York effort in the same prisons where he once served time.
The symmetry is almost too neat to be real. Except that it is.
Coming into this conversation wondering whether the premise was naive, I left it wondering whether the rest of us had simply been thinking about justice and about changemaking too small.
