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 Back to Prison: Day 1 

Picture of Michael Santos

Michael Santos

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We’ll document the tour we’re on to improve outcomes for all justice-impacted people. Today is day 1. We’re flying from Orange County to St. Louis, with a brief layover in Dallas. Looking forward to presenting at the federal prison in Greenville, IL.

November 1, 2022

Many people in our community led successful careers before going into the prison system. If they use their time inside wisely, I don’t have any doubt that in time, they’ll succeed again.

As a person who spent 9,500 days in prison, I urge people to begin by defining success.

What does success mean?

People will respond to that question differently. They may also change their responses as time passes.

I’m Michael Santos. I’m writing this message at 4:20 am on Tuesday, November 1, 2022. In about an hour, I’ll leave my house and drive to the John Wayne airport in Orange County, California for a trip that I’m enthusiastic to take. The trip relates to how I defined success at the start of my journey through prison.

By the time I completed my obligation to the Bureau of Prisons, in August 2013, I knew how I wanted to spend the rest of my life. Throughout the journey, I prepared for the career that I wanted to build.

I wanted to work toward improving the criminal justice system, opening more opportunities for people inside to emerge successfully—at the soonest possible time.

Today I’m boarding a flight to continue those efforts. I’ll fly to St. Louis first.

A few years ago, I visited St. Louis to meet with the leadership team of the Keefe Corporation. I wanted to partner with Keefe to bring the Prison Professors’ courses into the prison system. I laid out my plan to the CEO of Keefe, saying that I felt a calling to work toward improving outcomes of the criminal justice system.

Specifically, I wanted to influence legislators to pass laws that would reinstate parole, or open opportunities for people to earn freedom. The CEO of Keefe asked how I intended to accomplish that goal.

I told him that there would be many steps. First, I’d have to influence people in prison to work through programs that would prepare them for success upon release. I would need data to show that if they advanced through the courses that Prison Professors writes, they would be more inclined to lead law-abiding, successful lives once they got out.

If I gathered that data over time, I could build models showing the many ways that such programs benefited society. If legislators passed prison reform legislation, people would serve less time in prison. If people served less time in prison, people would be able to work in society and earn a living, support families, pay taxes. By helping more people emerge successfully, we could lower the prison population and build safer communities.

The CEO of Keefe reminded me that his business thrived on having a large prison population. A large prison population bought more Keefe products.

The complexity of working with prison profiteers is that our missions do not align. At Prison Professors, I want people to get out of prison earlier, and I want them to prosper when they get home.

My return on investment comes from improving outcomes for justice-impacted people. Other companies want to keep prisons full, and they want disenfranchised people to pay exorbitant fees for things like phone calls, music, or commissary—services that don’t cost anything in society.

Since our missions weren’t aligned, my proposed collaboration with Keefe didn’t get off the ground.

I had to keep trying. Fortunately, time in prison strengthened my resolve, helping me to deal with rejection and keep moving forward.

Over many years, I’ve continued working on the same goal—striving to improve outcomes for people in prison. And today’s trip furthers that mission. From St. Louis, I’ll rent a car and drive to Greenville, Illinois to make a series of presentations in the federal prison’s community.

Then, later this week, I’ll board a flight to Boston to meet with the head of US Probation for the district of Massachusetts. My wife is accompanying me. We’ll also meet with an executive at Bank of America as part of our effort to fund our nonprofit—more on that later.

On Saturday, we’ll rent a car and drive to NYC, where we’ll meet more prospective funders and collaborative partners. On Sunday, we’ll drive to DC to continue the fund-raising effort and development of the nonprofit. While in DC, I’ll meet with a former director of the Bureau of Prisons.

On Tuesday, I’ll board a train to Philadelphia to make a presentation in a state prison. When I return to DC, I’ll make a presentation at American University, speaking on the need for prison reform.

Following the presentation in DC, we’ll fly to Indianapolis. We’ll rent a car and drive to Lexington for another fund-raising excursion to advance the nonprofit. Then, we’ll drive to Terre Haute, Indiana, where I’ll make a series of presentations at the penitentiary.

We’ll be gone for 17 days on this trip. When I return to our home in Orange County, I’ll continue the efforts that I’m making to influence leaders to change the prison system.

Although I didn’t strike a deal with Keefe the last time I was in St. Louis, the incremental steps I’ve taken have gotten traction. We’ve introduced our program to jails and prisons across America, and more than 100,000 people access those digital courses every day through tablet providers or through direct relationships with prison systems.

These efforts are helping us gather data. The data we collect helps us refute arguments that the prison industrial complex makes about the need to confine more people than any other nation.

We can do better as a society. Data shows that we improve outcomes of America’s criminal justice system when we open opportunities for people to earn freedom in incremental stages. Rather than measuring justice through the turning of calendar pages, we should incentivize people to pursue excellence.

I began making that argument while I was in prison—writing a series of books on the subjects, and lesson plans to accompany those books. The system wasn’t ready to listen. Back then, the only mantra I heard was the importance of protecting the security of the institution.

Today we’re hearing a different message. We’re hearing a new director speak openly about the need to change the culture of the BOP and to strive toward helping more people emerge successfully.

During the first ten years that have passed since my release, I’ve worked hard to further this mission. It’s the slow and relentless work of advocacy. But I’m more optimistic than ever that changes will come.

And I give every recipient of this letter my word that I’ll keep striving toward that end.

I’ll send more reports on the trip to update our community on what I’m learning from the trip.


Michael Santos

PS: Forgive the typos. No time to edit as I’ve got to head to the airport now.

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