My 25-Year Journey Through Federal Prison... - Daily Love with Mastin Kipp

My 25-Year Journey Through Federal Prison…

On August 11, 1987, DEA agents arrested me. I was 23, living in Miami, and facing criminal charges in Seattle for my role in leading a scheme to distribute cocaine. The lawyer who represented me gave assurances that with the right amount of money, I could beat the charges. At the time I wasn’t ready to accept responsibility for the bad decisions I had made and I proceeded through trial, faced even more criminal charges, then sealed my fate when I told lies about my innocence from the witness stand. The jury didn’t buy the perjured testimony and convicted me on all counts. I faced a possible sentence of life without parole.

During that interim period between my conviction and sentence, I came across a wonderful book titled A Treasury of Philosophy. For the first time, my eyes opened to the wisdom of philosophy, especially after I read The Trial of Socrates. After reading about Socrates and his strength of character in responding to trials with dignity, I felt compelled to transform my life. Recognizing that there wouldn’t be anything I could say or do that would influence the sentence my judge was about to impose, I turned my attention inward and questioned how I could grow, even though struggle was sure to come. Rather than dwelling on challenges that would await the rest of my life, I made the commitment to spend my time in prison and beyond, working to reconcile with society.

But what did it mean to reconcile with society? I didn’t know the answer to that question. I was too young, too green, to immature to understand the depths of my troubles. I only understood that somehow I would have to find a way to redeem the bad decisions of my youth. I spoke publicly about that commitment.

Although I didn’t have a history of weapons or violence, my judge sentenced me to a 45-year sentence. Under the sentencing laws that existed at the time, such a sentence would require that I serve 26 years before I would conclude my obligation to the Bureau of Prisons. That was how I began a journey that spanned 9,135 days, taking me through prisons of every security level until my release on August 13, 2012.

My commitment to reconcile with society required that I think about what it would mean to become one with other members of the broader community. I thought about what citizens would expect of me. Those thoughts led to a three-part, principled plan I could follow. It would require that I:

1) educate myself,
2) contribute to society in meaningful, measurable ways, and
3) build a support network that would have a vested interest in my success upon release.

I’m immensely grateful to the inspiration I received from philosophers who educated me during that early stage of my journey. That pursuit of learning set me on a path through prison that empowered me. Rather than dwelling on all that was missing in my life because of my imprisonment, I could focus on steps I could take to advance prospects for a law-abiding, contributing life upon release. That strategy made me feel whole and one with society. My body may have been in prison, but mentally I was able to transcend the walls, creating meaning every day and living a life of relevance. In that way, I wasn’t in prison at all and I enjoyed more liberty than many people who take it for granted.


Michael Santos began serving a federal prison sentence on August 11, 1987.  Authorities released him 9,135 days later, on August 13, 2012.  He spent every day of his sentence in an effort to prepare for a law-abiding, contributing life, working to reconcile with society for the bad decisions of his youth. For more information on Michael and his journey, visit his website, Twitter, Quora, and Facebook.