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 Back to Prison: Day 8 

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Michael Santos

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Tuesday, November 8 (Day 8 of Prison Tour)

Dear Prison Community,

I began typing this letter while sitting at Union Station, Washington DC, waiting for a meeting with leaders of US Probation. While waiting for the people to arrive, I started to recap the stages we’ve made on our tour to improve outcomes for justice-impacted people. I finished writing the message early on Tuesday morning, before preparing for a busy day that would include a live presentation in a Pennsylvania state prison.

All these efforts are part of the multi-faceted effort to improve outcomes for justice-impacted people. As I did while serving 26 years in prison, and I’ve done since my release, I have to take incremental steps, building coalitions, to bring the positive changes that I want to see.

What are those changes? I want to create more mechanisms that will allow people in prison to work toward earning freedom. We need changes that would incentivize people to build a series of credentials that will open higher levels of liberty for them. To succeed in that goal, I must do the following:

  1. Create digital courses that I can spread across the country.
  2. Create mechanisms that will allow us to track data, showing how we’re improving contributing to improving lives of justice-impacted people and society.
  3. Persuading stakeholders who work in prisons to authorize the courses our team at Prison Professors creates.
  4. Persuading tablet manufacturers to collaborate and work with us.
  5. Persuading people in prison to join these efforts to build compelling cases for prison reform.
  6. Persuading voters and taxpayers on the need for prison reform.

While on this 17-day trip, I don’t have time to update each member of the community on every step I’m making. But while waiting to begin my drive to Pennsylvania, I wanted to provide an update with where I am today, and what I’ll be doing over the next week.

Please forgive any typos—as I don’t have time to read this over.

Day 1: Tuesday, St. Louis / Clayton

Carole and I boarded a flight in Orange County, California, to our first stop. We traveled to St. Louis, took an Uber to the city of Clayton. We intended to homebase out of Clayton, working from our hotel room until I could complete scheduled presentations at the Greenville federal prison.

Day 2: Wednesday, Rental car / Clayton

Carole and I went for a walk around the community in the early morning, then we worked from our hotel room for a few hours. In the afternoon, Carole and I began our exercise in the hotel gym, then we went to a local park. In the late afternoon we rented a car for my early-morning drive to Greenville.

Day 3: Thursday, Greenville Federal Prison

In the early morning, I drove from St. Louis to Greenville. It’s always exciting for me to speak with people in federal prison. Carole stayed back in the hotel working on administrative tasks for our business. To lessen the likelihood of spilling coffee on my white shirt or tie while driving, I wore athletic gear in the morning. I arrived at 6:00 am, about two hours earlier. In the parking lot of the local college, I changed clothes and then sat in a coffeeshop working until it was time to go. I showed up on time and staff members greeted me in the lobby of the camp. I made a presentation to the women serving time, which was a highlight of my day. Then, the warden treated his executive team and me for lunch. Following our lunch, we returned to the prison and I got the privilege of presenting for the men serving sentences in the medium-security prison.

Day 4: Friday, St. Louis to Boston: US Probation

At 3:30 in the morning, Carole and I left our hotel for the St. Louis airport. We arrived in Boston in the early morning, rented a car, and drove to a hotel we reserved in the Back Bay. After dropping off Carole, I ran for a meeting with three US Probation Officers. My purpose in the meeting was to discuss the work we’re doing to improve outcomes for people in prison and opening a relationship with US Probation. These types of business-development meetings take time, but they’re necessary as part of our comprehensive efforts to improve outcomes of America’s prison system. Following my meeting with the probation officers, I made a series of videos around Boston. We would use those videos as part of our curriculum.

Day 5: Saturday, Boston to Harvard to Yale to Jay Jordan to NYC

In the early morning on Saturday, Carole and I ran to Harvard. During our run, I paused to make a series of videos. I wanted to record the many ways that professors at Harvard mentored me while I served my sentence. They opened opportunities for me to grow. After returning to the hotel, Carole and I packed and we drove to Yale University. Again, we made a series of videos. Then we drove to New York City and we had dinner with our friend Jay. Jay served time in the California Prison System for gang-related offenses. Today he leads a nonprofit with an annual budget of more than $25 million; his nonprofit strives to work toward community safety. Following our dinner, Carole and I drove to our hotel in midtown and we walked through Times Square.

Day 6: Sunday, NYC to Hofstra to Princeton to DC

In the early morning, I left the hotel to get Coffee for Carole and me. I saw thousands of people gathering in preparation for the New York City marathon. Carole and I completed our morning work in the hotel, then we went out for a run through Central Park. The marathon runners impressed us, especially those who completed the marathon despite their physical handicaps. While incarcerated, I ran many marathon distances around prison tracks. Distance running strengthened me through the journey and I filmed a series of videos on Sunday morning to convey the message. Following our exercise, we drove to Hofstra University and then to Princeton University, continuing the effort to record recollections of how those universities helped me prepare for success while I served my sentence. We intended to visit the University of Pennsylvania, but after leaving Princeton, the sun had gone down and we drove straight to Washington DC. In Washington, we stayed with a friend who had been very helpful to me throughout the final 15 years that I served in prison.

Day 7: Monday, Washington DC

In the morning, Carole and I drove to Union Station. I had a m

eeting with the retired head of federal probation, and a current leader of probation. We discussed the work that I’m doing to expand my reach inside of jails and prisons across America, and I helped them see how the digital learning courses I create could contribute to probation. The goal would be to record efforts that people make in prison to prepare for success upon release. While I conducted my meeting with probation, Carole sat at an adjacent table doing administrative work and training with our team with a conference all. Following our time at Union Station, Carole and I went to exercise in Rock Creek Park in Northwest Washington.

Day 8: Tuesday, Philadelphia Prison

This morning I will drive with a former director of the BOP to Pennsylvania. I’ll make a presentation in a state prison and interact with leaders of that system, showing the importance of incentivizing people to pursue excellence. I’ll also meet with researchers to learn more about how we can conduct an empirical study that would measure results of our program.

Day 9: Wednesday, Halim and Jon Gustin

Tomorrow I’m scheduled to meet with Halim Flowers, a friend a business partner who once served a double life sentence. I’ll have dinner with Jon Gustin, who previously led the BOP’s home confinement program.

Day 10: Thursday, American U

I’ll present at American University, helping students understand the importance of reforms that can improve outcomes of America’s prison system.

Day 11: Friday, Indianapolis

Carole and I will fly to Indianapolis, rent a car, and drive to Lexington for a meeting with potential funders of our nonprofit.

Day 12: Saturday, Lexington

We’ll continue our meeting with potential funders of our nonprofit in Lexington.

Day 13: Sunday, Louisville

We’ll drive to Louisville for a meeting with a potential sponsor of our nonprofit.

Day 14: Monday, Terre Haute

We’ll drive to Terre Haute in preparation for presentations that I’ll make in the federal prison.

Day 15: Tuesday, Terre Haute

I’ll make a full day of presentations in the federal prison.

Day 15: Wednesday, Terre Haute

I’ll make a full day of presentations in the federal prison.

Day 16: Thursday, Home

I’m scheduled to fly back to Orange County, California.

When time allows, I’ll provide another update on our tour where Carole and I are working to improve outcomes for justice-impacted people.

Remember that to reach our goal of changing policies, improving outcomes, and changing laws, we need people in prison to help our efforts. The more we can show that people in prison are working to earn freedom, the more successful we become in bringing reforms like the First Step Act and getting the BOP to advance initiatives that will help people succeed upon release. I hope to meet people in all federal prisons over the next 12 months.

With best wishes to each of you, I send my regards.


Michael Santos

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