Jessica Jackson: An Unexpected Hero

I know what hopelessness feels like.

I am serving a 30-year federal sentence for a low-level, nonviolent offense. I have spent years in solitary confinement and in maximum-security federal prisons where violence, lockdowns, and institutional indifference are part of everyday life.

When you are serving decades in federal prison, time takes on a different meaning. Birthdays pass. Holidays come and go. Parents and friends grow old. People you love die. Families change. Children grow up without you.

And because there is no parole in the federal system, there is often no obvious way out.

That is why people who fight for criminal justice reform matter to me.

A few years ago, I wrote about one of those people: Jessica Jackson.

At the time, she was already an extraordinary advocate—a human-rights lawyer, co-founder of #cut50, and one of the people who helped push the First Step Act across the finish line.

A lot has happened since then.

Jessica is now CEO of REFORM Alliance, one of the country's leading criminal-justice reform organizations. Since REFORM was founded, it has helped pass bipartisan legislation in states across the country, creating pathways for hundreds of thousands of people to leave probation and parole earlier. In 2025 alone, REFORM says its legislative work affected more than 188,000 people. By the beginning of 2026, the organization reported 22 laws passed in 12 states and nearly one million people given pathways out of supervision. (REFORM Alliance)

But the numbers aren't what make Jessica's story remarkable.

Her story starts in a courthouse bathroom.

Tears in a Courthouse Bathroom

Twenty years ago, Jessica Jackson was 22 years old, holding her two-month-old baby and crying in a courthouse bathroom in Georgia.

Her husband had just been sentenced to six years in prison for a nonviolent burglary offense.

Jessica had no high school diploma. She didn't have a job. She wasn't a lawyer. She wasn't a criminal-justice expert. She wasn't someone with political connections or an established career.

She was a young mother who suddenly had no idea what her future looked like.

She has described watching her husband get taken away and realizing that the system had reduced him to the worst thing he had done.

“I knew he was a good dad, a good son, an employer, a great employee with a hard work ethic,” she said. “He’d made a bad decision, but there was so much good in him as well.”

That moment changed her life.

She decided she would become a lawyer.

Her mother wasn't convinced.

Jessica didn't exactly have the résumé for it.

But she went back to school anyway.

An Unlikely Lawyer

Jessica eventually earned her bachelor's degree from the University of South Florida and her law degree from Santa Clara University School of Law.

She began her legal career representing people facing the death penalty in post-conviction proceedings.

That work changed her understanding of the criminal justice system.

Death-penalty cases expose the machinery of punishment in its most extreme form. But the problems Jessica saw were not limited to death cases. She saw families torn apart, people discarded, and human beings reduced to convictions and case numbers.

She became convinced that fighting individual cases wasn't enough.

The system itself had to change.

And Jessica wasn't content to wait for someone else to change it.

The Napkin

Jessica's next move was even more ambitious.

She met Van Jones, and over breakfast they began sketching out an idea on a napkin: an effort to cut America's prison population in half.

That became #cut50.

The goal sounded unrealistic. America had spent decades building a massive system of incarceration. Politicians had made careers promising to be tougher on crime. Reform was often treated as a partisan issue.

Jessica didn't seem particularly interested in what was supposed to be possible.

She was interested in what was necessary.

#cut50 built an unusual coalition around criminal-justice reform, bringing together people who did not ordinarily agree on much.

And then came the First Step Act.

Getting the First Step Act Across the Finish Line

The First Step Act became law in December 2018.

#cut50 played a major role in building the bipartisan coalition behind it, and Jessica was one of the central advocates pushing the legislation forward. (Santa Clara Law)

The law changed federal sentencing and prison policy in significant ways.

For people like me, that matters.

Because sentencing laws are not abstract.

They determine whether a person spends 10 years in prison or 30. Whether a father watches his children grow up or receives photographs through a visiting-room window. Whether an elderly prisoner dies behind bars or gets to go home.

The First Step Act didn't fix everything.

Far from it.

But it proved something important:

The system can change.

Jessica Didn't Stop There

This is where my original article needs the biggest update.

Jessica's work didn't end when the First Step Act became law.

She went on to become a founding member of REFORM Alliance, an organization focused primarily on transforming America's probation and parole systems. In 2024, she became its CEO. (REFORM Alliance)

That matters because America's criminal-justice system doesn't end at the prison gate.

Millions of people are living under probation and parole supervision. Rules that are supposed to help people successfully return to society can instead become another mechanism for trapping people in the system.

A technical violation can send someone back to prison.

A supervision term can drag on for years.

And a system designed to help people transition home can become another form of punishment.

Jessica and REFORM have focused heavily on changing that.

The organization says it has helped pass 22 laws in 12 states, creating pathways for nearly one million people to exit supervision. (REFORM Alliance)

In Virginia, for example, REFORM backed bipartisan legislation designed to cap probation terms, eliminate outdated post-release supervision, and create incentives tied to employment and education. (REFORM Alliance)

That is a very different kind of reform from simply giving speeches about mass incarceration.

It is changing the rules.

From California Death Row to the World Stage

Jessica's work has also moved beyond the United States.

She was named a Young Global Leader by the World Economic Forum. (Santa Clara Law)

Her work on reentry has also taken on an international dimension. According to Santa Clara Law, she helped advance a joint United Nations statement signed by 74 member states supporting international cooperation around the reintegration of people returning to their communities after incarceration. (Santa Clara Law)

That is a remarkable distance to travel.

A woman who once sat crying in a courthouse bathroom because the criminal-justice system had taken her husband away was now helping shape conversations about incarceration and reentry on an international stage.

Why Jessica Matters to Me

I have spent 16 years inside the federal prison system.

I've watched people disappear.

I've watched men receive sentences that made little sense even when they were imposed. I've watched laws change while the people serving yesterday's sentences remained trapped under them. I've watched people lose hope because they couldn't afford lawyers, didn't have connections, or simply didn't know where to turn.

I've also watched people change.

I've watched men become better fathers from behind prison walls. I've watched people earn degrees, confront addiction, mentor younger prisoners, discover faith, and devote themselves to helping others.

The problem is that the criminal-justice system is often much better at punishing people than recognizing change.

That's why advocates matter.

And that's why I've followed Jessica Jackson's career for so long.

She didn't come from the traditional world of criminal-justice reform.

She didn't start with a law degree, a political network, or a powerful résumé.

She started with a husband being taken away and a baby in her arms.

Then she went back to school.

Then she became a lawyer.

Then she helped build a national movement.

Then she helped pass federal legislation.

Then she helped build another organization focused on changing probation and parole.

And now she leads that organization.

Jessica Jackson didn't inherit a place in the criminal-justice establishment. She fought her way into it. Then she started changing it.

That's what makes her an unexpected hero.

And, in my view, a pretty extraordinary one.