Digestly

Mar 19, 2025

What Happens After Spending Decades in Prison-Michael Santos

Soft White Underbelly - What Happens After Spending Decades in Prison-Michael Santos

Michael Santos, founder of Prison Professors, recounts his transformation from a drug trafficker sentenced to 45 years in prison to an advocate for prison reform. Inspired by figures like Frederick Douglass and Socrates, Santos used his time in solitary confinement to reflect and plan a path forward. He focused on education, contributing to society, and building a support network. Santos earned degrees while incarcerated and published books on prison reform, eventually becoming a professor and speaker advocating for changes in the prison system. His story highlights the importance of self-directed change and the potential for rehabilitation through education and personal development. Santos now runs programs to help inmates prepare for life after prison, emphasizing the need for systemic change in how society views and treats incarcerated individuals.

Key Points:

  • Michael Santos transformed his life in prison by focusing on education, earning degrees, and writing books on prison reform.
  • He was inspired by historical figures like Frederick Douglass and Socrates, which motivated him to change his mindset and actions.
  • Santos advocates for prison reform, emphasizing the importance of education and personal development for inmates.
  • He developed programs to help inmates prepare for life after prison, aiming to reduce recidivism and promote rehabilitation.
  • Santos' story demonstrates the potential for personal transformation and the need for systemic change in the prison system.

Details:

1. 🎬 From Scarface to Crime: Michael's Early Choices

  • Michael Santos, founder of Prison Professors, served a 45-year prison term after making poor life choices influenced by the movie 'Scarface'.
  • Despite growing up in an affluent area in North Seattle, with access to ample opportunities and education, Michael was swayed by the film's portrayal of a glamorous lifestyle associated with crime.
  • The movie 'Scarface' played a pivotal role in shaping Michael's perception of success and wealth, leading him to pursue a path that eventually resulted in his imprisonment.
  • Although Michael was not a drug user, the influence of 'Scarface' was significant enough to override the positive influences and opportunities available to him during his upbringing.
  • This case highlights the profound impact media can have on individuals' life choices, especially when they lack a strong, grounded perspective.

2. 💰 Rise to Kingpin: The Drug Trafficking Scheme

  • Initially lacked knowledge about drugs but leveraged connections with cocaine users to gather information.
  • Discovered a significant pricing discrepancy: a kilogram of cocaine cost $50,000 in North Seattle, but only $220,000 in Miami, highlighting a lucrative opportunity.
  • Enlisted help from acquaintances to transport cocaine from Miami to North Seattle, offering $5,000 for their assistance.
  • Secured funding by misleading his father into believing the money was for a construction business, demonstrating resourcefulness in financing the operation.
  • Projected a profit of $30,000 per kilogram of cocaine trafficked, showcasing the scheme's high-profit potential.
  • Faced initial challenges such as gaining trust and ensuring the safe transportation of drugs, but strategic planning and leveraging personal relationships overcame these hurdles.

3. 🚨 Legal Troubles: Arrest and Trial Challenges

  • A transaction led to earning a few hundred thousand dollars at the age of 20, escalating criminal activity to a serious crime level with the role of a Kingpin.
  • An investigation was ongoing, but initially, the individual wasn't a target. To avoid becoming one, relocation to the south of Spain occurred.
  • Despite no direct evidence of cocaine possession or incriminating phone calls, the individual was arrested and faced life imprisonment due to the lifestyle and unexplained wealth.
  • The arrest happened shortly after returning to the United States, indicating that absence did not deter legal action.
  • During the trial, the prosecution focused on lifestyle evidence and financial records, while the defense highlighted the lack of direct evidence.

4. 📚 Prison Realization: Learning from History

  • The narrator realized the importance of receiving honest legal advice rather than just hearing what they wanted, which led to poor decision-making and facing a serious sentence.
  • Initially, the narrator was not granted bail post-arrest and was kept in solitary confinement, which was a new and isolating experience for them at 23 years old.
  • In the federal system, an indictment often leads to conviction, a fact the narrator was unaware of until later.
  • During the trial, close associates testified against the narrator, leading to a conviction on multiple counts related to a drug trafficking scheme.
  • The narrator had a misconception that not directly handling drugs meant they were not breaking the law, but they were charged with a 'continuing criminal enterprise' carrying a life sentence.
  • Post-conviction, a pivotal moment occurred when an officer provided the narrator with a book about Frederick Douglass, inspiring them to pursue personal transformation through education and self-betterment.
  • Frederick Douglass's story emphasized overcoming slavery through learning to read, write, and communicate effectively, which led him to become an influential abolitionist.
  • The narrator was similarly inspired by Plato's 'Republic' and Socrates' story of facing death for his beliefs, reinforcing the idea of accepting responsibility and the importance of laws even if they are flawed.
  • The combination of Douglass's and Socrates' philosophies prompted the narrator to seek personal change and integrity within the confines of their situation.

5. 🧠 Developing a Prison Strategy: Education and Reform

  • Facing a potential sentence of 10 years to life, the individual crafted a transformative strategy to shift their identity from a 'Coke trafficker' to a reformed person.
  • The strategy comprised three key components: education, societal contribution, and building a support system.
  • Pursuing education was deemed essential to demonstrate a commitment to personal reform and a departure from a criminal identity.
  • Contributing to society in measurable ways was identified as a method to show genuine change and reconcile with the community.
  • Building a robust support system was crucial for gaining the trust of others and ensuring a successful reintegration into society.
  • The strategy aimed to maintain dignity and create opportunities for a successful life post-release, despite uncertainties regarding the length of imprisonment.

6. ✍️ Building a New Identity: Writing and Advocacy

  • The speaker was inspired by historical figures like Frederick Douglas and Socrates to change his life through writing and advocacy during his time in prison.
  • He actively engaged the media by writing a letter to a newspaper, expressing regret for his past and inviting a journalist to hear his story, which resulted in media coverage before his sentencing.
  • Despite facing a 45-year sentence in federal prison during the tough war on drugs era, the speaker used this challenge to mentally prepare and focus on personal growth.
  • In prison, he found solace and hope in small freedoms like seeing the sky, which provided a stark contrast to the confinement he experienced.
  • The speaker emphasized the importance of taking personal responsibility and actively seeking change, rather than passively waiting for it to happen.
  • His advocacy efforts led to significant media attention and public awareness, highlighting the harsh realities of the prison system and the potential for personal transformation.

7. 📖 Academic Pursuits: Education Behind Bars

  • Michael Santos realized the need to transform his life and avoid being a criminal. He began by focusing on education as a means to change his life trajectory.
  • Understanding that he would spend a significant time in prison, Santos planned to use education to build a new path, starting by writing letters to universities to seek educational opportunities.
  • Despite initial challenges, Santos succeeded in enrolling in a university, which marked the beginning of his educational journey and shifted his identity from a prisoner to a student.
  • He pursued higher education with determination, eventually working towards an undergraduate degree, and expressed interest in law school, although institutional constraints limited his options.
  • Santos communicated with law schools, and although they couldn't offer a law degree, Hofstra Law School offered flexibility for a graduate degree, leading him to study mass incarceration.
  • His graduate studies focused on the prison system and the social injustices of mass incarceration, emphasizing its disproportionate impact on poor people and people of color.
  • Santos engaged in ethnographic work, interviewing fellow inmates and sharing their stories in academic contexts, thus contributing to the academic discourse on incarceration.
  • Through education, Santos built a support network, connecting with professors and academics, which facilitated his involvement in publishing and academic contributions.
  • Ultimately, his educational pursuits created opportunities to publish in peer-reviewed journals and participate in academic projects, further advancing his goal of contributing to societal change.

8. 💼 Publications and Partnerships: Expanding Influence

8.1. Momentum Building Through Writing

8.2. Publishing Opportunities and Academic Engagement

8.3. Strategy for Systemic Change

8.4. Personal Impact and Relationship Development

8.5. Career and System Change Advocacy

9. ❤️ Love and Support: Building a Relationship in Prison

  • The speaker emphasizes the importance of building a meaningful career post-release, with their partner playing a crucial role as a link to the outside world.
  • They have navigated through various prison security levels, indicating adaptability and progress, moving from high security to a camp.
  • Authored books while incarcerated, aiming to build credibility and advocate for change, successfully securing a publishing deal with St Martin's Press.
  • Faced significant challenges in publishing from prison, including solitary confinement, yet persisted in writing and sharing experiences.
  • Their partner demonstrated significant commitment by relocating to be closer, showing the personal sacrifices necessary to sustain the relationship.
  • Despite restrictions, the speaker continued to publish, resulting in multiple transfers between prisons, showcasing resilience and dedication to their goals and relationship.
  • The emotional strength of the relationship was tested, with both partners making sacrifices to stay connected and support each other.

10. 🚗 Transitioning to Freedom: Life Post-Release

10.1. Writing in Prison

10.2. Relocation and Writing Opportunities

10.3. Parole and Release Preparation

10.4. Reunion and Technological Adjustment

10.5. Post-Prison Plans and Support System

10.6. Navigating Life Post-Release

11. 🎓 From Prisoner to Professor: Academic and Advocacy Work

  • After being released from 25 years in prison, the subject had difficulty adjusting to normal activities, such as driving, which took several months to relearn despite having a license.
  • The subject gained attention from the San Francisco Chronicle due to his writings about prison life, which he had been publishing through a website with help from his wife.
  • Following media coverage, he received invitations from universities to speak, despite never having attended university himself, highlighting the impact of his written work and advocacy.
  • San Francisco State University offered him a professorship after reading his published works, particularly noting that his books were part of graduate studies at the institution.
  • He created a course titled 'The Architecture of Incarceration' to educate students on the historical responses to crime and advocate for prison reform.
  • His advocacy focuses on changing the prison system by incentivizing positive behavior rather than focusing solely on punishment, aiming to reduce recidivism rates.
  • He published an article in the UC Hastings Law Journal advocating for prison reform during a tough-on-crime era, which contributed to his recognition and speaking engagements at judicial conferences.

12. 🌍 Changing the System: Advocacy for Prison Reform

  • The speaker leveraged influential figures, such as federal judges and prison officials, to advocate for prison reform, emphasizing the potential for personal transformation regardless of the system's judgment.
  • A transformational program, 'Preparing for Success after Prison,' was introduced in gang-related and high-security prisons, reducing violence and inspiring inmates by showcasing avenues for positive change.
  • The program, supported by collaborations with nonprofits like the Adobo Foundation, expanded nationwide, impacting a million people through direct engagement in prisons.
  • Digital and video storytelling were key strategies used to connect with inmates and promote the message that transformation is possible without waiting for systemic changes.
  • The program emphasized the development of education, critical thinking, and self-directed work ethic among inmates, empowering them for better future prospects.
  • Drawing inspiration from figures like Nelson Mandela and Frederick Douglass, the speaker encouraged inmates to view themselves as capable individuals beyond their incarceration.

13. 📣 Spreading the Message: Empowerment and Education

  • The speaker highlights the negative outcomes of current prison adjustments, such as homelessness and legal issues, stressing the need for a narrative change.
  • They engage in prison outreach through videos and visits, advocating for a reform system that helps inmates reach their highest potential.
  • Inspired by Airbnb's Brian Chesky, the speaker launched prisonprofessorstalent.com, a platform to aid inmates in showcasing their skills and experiences.
  • The platform encourages inmates to document journeys, write book reports, journal, and create release plans to improve post-release opportunities and counter societal biases.
  • The initiative aims to break the cycle of failure by providing inmates tools for successful reintegration into society.
  • The speaker addresses human rights violations in prisons and emphasizes education and empowerment to prevent intergenerational cycles of failure.
  • By sharing personal success stories, they inspire both the incarcerated and the public, advocating for rehabilitation over punishment.
View Full Content
Upgrade to Plus to unlock complete episodes, key insights, and in-depth analysis
Starting at $5/month. Cancel anytime.