"Redefined": Inside the 2026 Wardens' Conference and the Slow, Stubborn Work of Changing a Prison System

When every warden in the Federal Bureau of Prisons gathers in one room in Washington, D.C., it's worth asking what brought them there. In 2026, the answer was a single word printed on the conference brochure: Redefined.

In a recent video conversation, host Justin Paperny sat down with his longtime friend Michael Santos to unpack what happened at that conference — and what it signals for the more than one million people touched by America's criminal justice system. What follows is drawn entirely from that interview.

A conference built around a single idea

The gathering brought together the wardens of all of the federal system's roughly 123 prisons, along with the Bureau's regional directors and a lineup of outside speakers — business leaders, advocates, and others invited to talk about "a different way of running prisons," as Santos put it. The theme of redefining was no accident. It came directly from the man hosting the event: Deputy Director Josh Smith.

Santos first met Smith about a year earlier, in July 2025, at the Bureau's headquarters in D.C. Smith had just stepped into the role, and he was candid about the timeline. "It's going to take him about a year," Santos recalled Smith telling him, "to really work on some of the internal complications." Smith was a businessman entering a 40,000-employee bureaucracy long governed by unions, policies, procedures, and historical precedent — not, in Santos's words, by "being innovative and courageous."

A year later, the conference was the visible result of that groundwork. Smith had reshaped the leadership tier first, bringing the regional directors into alignment. There are now six regional directors — three appointed, three serving in an acting capacity — and Santos says he knows all six and considers them aligned with the movement. Only after that did Smith bring every warden together in one room to hear the case for change.

Santos doesn't pretend this happens quickly, and he's sympathetic to families who find the pace agonizing. "They want an immediate change," he said. "I understand that, and I empathize with them." But shifting a system this size means retraining tens of thousands of employees and getting "all the parts moving in the same direction" — work measured in years, not weeks.

The unlikely résumé of a deputy director

Why is Smith such a believer? Because, Santos explains, he has lived it.

Smith was born into poverty in Tennessee. His father left when he was two. By 16, by his own account, he had become skilled at breaking into houses and had accumulated 10 felonies. At 18, he was in federal prison as a drug offender, serving a five-year sentence.

Prison, improbably, became his first classroom. It was the era of the Enron scandal, and the camp filled with bankers, finance professionals, and lawyers — the first college-educated people Smith had ever met. He introduced himself, tried to help, and started asking questions: What does a banker do? What does a finance guy do? What is business? They handed him books. He taught himself.

Release didn't come easily. This was before the First Step Act. His halfway house was actually a jail — the same one where he'd been held before trial — and he found it worse than custody, though with a little more liberty. Every job application that disclosed his record went unanswered. So he built his own income instead, starting a small company doing the work nobody else wanted: cleaning gutters and basements, waterproofing, prepping roofs. He hired other formerly incarcerated people, and in doing so heard firsthand how probation officers and authority figures spoke about people with records — something that shaped his thinking.

The numbers tell the rest. He made $15,000 his first year. It took five years before he cleared $30,000 in a year. But by year ten, he reported his first million-dollar year. Private equity came knocking with an offer he hadn't been looking for, and he sold — roughly five or six years ago.

A deeply religious man, Smith had made a vow: once he had enough wealth, he would work to change the prison system that changed his life. He and his wife donated millions — Santos recalls something like $8 to $10 million — to his own foundation, The Fourth Purpose, to improve prisons in America and abroad. That work drew notice from Tennessee's governor, then from the president's children, and eventually a meeting with President Trump, who pardoned him and offered him a role running the Bureau of Prisons.

Notably, Santos says Smith could have been the director — but chose deputy director instead. The director's job is political: Congress, legislatures, budgets. The deputy director is "the one that's got your feet on the ground and doing things." Smith wanted the hands-on role, and he wanted to build changes durable enough to outlast both himself and any administration. "He's a true believer," Santos said. "He doesn't have to be in the role."

What it's like to walk into 81 prisons

Santos knows the federal system from the inside — he served 26 years, finishing his sentence in 2013. His first presentation inside a federal prison came in 2015, at USP Atwater, with the support of that institution's warden. But back then, support was local and inconsistent. Real change, he learned, requires national backing.

Under the new leadership, the reception has transformed. Santos says he has now visited 81 of the system's roughly 123 federal prisons and held personal conversations with at least 50 wardens. The difference, he believes, comes from the top: the deputy director is himself formerly incarcerated and openly supportive. "They see me differently than at any time before."

That shift was on display at the conference. The program opened Tuesday and built deliberately toward the formerly incarcerated speakers on Wednesday. Before Santos spoke, the wardens heard from world-class leaders — the chairman and CEO of Ace Hardware (a company he cites at roughly $30 billion in annual revenue and around 100,000 employees) and the first Black woman to serve as president of a private aviation company. Their message was about leadership: it isn't about yourself; it's about getting an entire organization moving in the same direction. The aviation executive spoke about overcoming a culture dominated by white males who didn't necessarily want to listen to a woman — and the parallel landed. If she could change a culture like that, maybe the wardens could too. And maybe, the logic went, they should listen to the people who had actually lived through the system.

By the time Santos and others — including Damon West, who has been to 30 or 40 prisons — took the stage, the room was ready. "It was just a totally different acceptance," Santos said.

"Everything we do is free"

Justin pressed on a point worth emphasizing: none of this is funded by the Bureau of Prisons, and no one in prison pays for it. Santos was emphatic. He has never taken a penny from the nonprofit. The Bureau has never paid the organization. Around the time of COVID and the budget cuts that followed, the operation became a fully nonrevenue-generating nonprofit, funded by book sales on Amazon — with proceeds flowing directly into the nonprofit — along with support from individuals, board members, and others.

The scale is significant: more than 8,000 profiles and 13-plus million words on the website, approaching 9,000 participants, on a budget Santos pegs near a million dollars a year. As it grows, he expects the cost per participant to fall below 20 cents a day.

The advocates who carried the message

A striking feature of the conference was who delivered the case for change — and to whom.

Alice Johnson. Convicted of a drug offense and sentenced to life plus twenty years, Johnson spent her time working to improve the system. Her story reached Kim Kardashian, then Ivanka Trump, then the president, who commuted her sentence. After coming home she continued her advocacy, earned a full pardon, and was named to a brand-new role: pardon czar of the United States. Anyone seeking executive clemency now goes through her office first. At the conference, her message to the wardens was direct: the president is interested in righting wrongs, and wardens have unique insight into the people in their institutions. A complex warden may oversee thousands, but associate wardens, unit managers, and department heads each know the people under them. When they find someone genuinely worthy of relief, she wants their names.

Rabbi Weiss. Representing a tradition Santos describes as among the most influential in prison reform — alongside the Aleph Institute — Rabbi Weiss advocated for expanding the First Step Act and implementing a furlough program. Furloughs, Santos notes, are already authorized under the Code of Federal Regulations; a warden, as "the CEO of his institution," can grant them. Getting wardens to actually use that authority takes advocacy. Santos shared how Smith introduced the rabbi: rather than make him prove his worth, Smith said, in effect, you already have credibility here — tell us how we can help. That spirit, Santos said, is "very different from anything else we've ever seen in the agency."

Brett Tolman. A former U.S. attorney appointed under President George W. Bush, Tolman brings credibility no one can dismiss as soft on crime — he prosecuted the kidnappers of Elizabeth Smart. His framing is "smart on crime": be a good steward of resources, don't waste them. With a law-and-order pedigree, he could tell the wardens that Smith's leadership has the full support of both the president and people like himself.

Santos also noted others in attendance, including Peter Navarro — an influential figure in the president's cabinet who was himself incarcerated.

Leadership that removes obstacles

Santos repeatedly framed what's happening as a leadership story that spreads from the top down: from the deputy director and Director Marshall, to the regional directors, to the wardens. And leadership, he stressed, sometimes means hard personnel decisions. He pointed to Burl Cain — the longtime leader of Angola, once among America's deadliest prisons, who later took over a troubled Mississippi corrections system and removed wardens who wouldn't get on board. "If they're not gonna be with my program, they can't be with me." Santos said Smith and the leadership team have shown the same willingness to remove people not buying into the change. "A leader has to get everybody moving in the same direction."

The harder fight: expanding who qualifies

Not everyone benefits from the First Step Act today. Santos pointed to CZ — the founder of Binance — who served his sentence in a low-security prison because of immigration status, under harsher conditions and at a higher security level than warranted, a circumstance Santos calls "a great injustice." Tens of thousands of people, he says, are in similar positions, and thousands who qualify for furloughs still don't get them.

Changing that isn't like flipping a light switch. Santos likes to contrast it with a restaurant changing its opening time from 8 a.m. to 7 a.m. — a simple sign in the window. Changing policy for the entire Department of Justice is something else entirely. His strategy is deliberately bottom-up: he holds no power himself — "My name is Michael Santos. I'm 16377-004" — so he works to get wardens advocating, who move regional directors, who move the director, who can press Congress. Some goals require a change in law, which means Congress and a presidential signature; others can be achieved through policy, which sits within the director's and deputy director's authority. His most audacious long-term goal: bringing back federal parole.

He's also realistic about public sentiment. "A lot of people in America... would say, if a judge sentenced you to five years, I don't want you to get out in four years, eleven months, and two weeks." Advocacy, in his view, means meeting that reality with a credible plan — and asking people in prison to help build the record that makes the case.

A new economy meets an old cause

One of the more unexpected threads is how the work gets funded from around the world. Santos worked closely with CZ as he prepared for and served four months in prison, collaborating on the book Freedom of Money and narrating its audiobook. Within two days of the book's release — it mentions Santos's organization — someone launched a Web3 token, the Prison Professors token (PP), on decentralized exchanges, without Santos's involvement or even his prior knowledge.

He found out when his wife asked whether CZ had sent him $5,000. He hadn't. It turned out to be cryptocurrency in the nonprofit's account — not from one person, but from hundreds. By the token's design, a smart contract automatically routes 3% of each purchase to the nonprofit's treasury, no human intervention possible. Santos says the community — which he ties to the BNB ecosystem CZ originated — has generated the equivalent of around $500,000 in crypto for the mission. He's pledged not to touch those funds until at least the summer of 2027, until he knows how much is truly there.

What "exceptional" actually means

Toward the end, Justin asked the question many families ask: isn't avoiding disciplinary infractions and attending programs simply what's expected? How does anyone become exceptional?

Santos answered with a thought experiment. Picture the personality of someone who builds a career working in a federal prison. Are they there, he asked, to find a way to get you home as soon as possible? Probably not. He turned it around: before you were ever touched by the system, what did you think when you read about an accused criminal in the paper? The honest answer, for most people, is lock them up. That, he says, is the cynical mindset a person in prison must persuade — and you don't move a cynic by doing the bare minimum.

His metaphor was McDonald's. It isn't the best cheeseburger anyone's ever had, he noted — but it's the best-selling, because Ray Kroc knew how to build something consistent and recognizable. People in prison, he argues, have to think the same way: build a body of work that makes them an exception, document it transparently, and become, in the phrase he returns to again and again, "the CEO of your life."

The bottom line

Santos doesn't promise change this week. "There are a lot of people who don't like what I do," he acknowledged. "There are a lot of people that would like to see me fail." But he points to changes he calls "abundantly clear": tens of thousands of people receiving earned time credits, more phone minutes, tablets with educational material, and — he believes — furloughs and expanded home confinement on the way.

The two biggest changes, in his telling, are the people now in the chairs that matter: a formerly incarcerated deputy director running the Bureau, and a formerly incarcerated pardon czar reviewing every clemency application. "Those are massive changes that are gonna influence the lives of a million people."

The catch — and the call to action — is that the system increasingly rewards individual effort. "Every individual is going to have to build a case to demonstrate why are you worthy." That, Santos says, is exactly why he built a free platform for people to do it.

As the conversation closed, he drew one line clearly. Justin runs commercial enterprises; Santos is "strictly a nonprofit, mission focused" — hoping to bring changes "that will benefit everybody that goes through America's criminal justice system."