I began Prison Professor as a commercial enterprise after I finished my term. Later, Shon Hopwood joined the initiative, and I rebranded as Prison Professors. Our relationship ended around 2018. Since then, we’ve restructured as a nonprofit entity, striving to open more pathways for people to earn freedom through merit. In this role, as a digital content creator, I receive questions from staff members about my relationship with Shon Hopwood, and why he is profiled in many of our courses.
For that reason, it makes sense for me to write about the collateral consequences and long arc of a criminal conviction.
Years ago, while I was still in prison, I received a letter from an editor at Random House.
I had published a book with St. Martin’s Press, and other editors had begun to notice my work. One editor reached out to tell me about a manuscript that Shon Hopwood wrote. He asked if I would consider writing a blurb for the book’s jacket cover.
I agreed to read the manuscript, and after reading Law Man: My Story of Robbing Banks, Winning Supreme Court Cases, and Redemption, I wrote the following blurb:
“Shon Hopwood's remarkable accomplishments show that a man defines himself not by the decisions of his past, but through the perseverance and passion he musters to become something more. His inspiring story, skillfully written, provides compelling evidence that even from within the dark depths of a lengthy prison term through discipline and commitment a man can tap into the light of liberty. Deliberate choices Mr. Hopwood made led to more than changing the law at the highest levels and advancing justice for all. Perhaps even more important, he gives us a living breathing example of how an incarcerated individual can thrive, creating meaning and self-respect through a commitment to improving the lives of others.”
After my release on August 12, 2013, I received permission from U.S. Probation to travel. While visiting my sister Julie in Seattle, Carole and I made a point of visiting Shon. He had just settled in the Seattle area to begin law school at the University of Washington.
That was the beginning of our friendship.
Over the years, we spoke together at events and shared a mutual interest in reforming America’s prison system. I continued advocating for merit-based pathways—ideas I wrote about in Inside: Life Behind Bars in America and later in Earning Freedom: Conquering a 45-Year Sentence. I believed Shon could help advance those ideas, and I invited him to join Prison Professors during its early commercial phase.
Later, 60 Minutes profiled his remarkable story. That exposure led to conversations at the highest levels of government. Jared Kushner invited Shon to participate in discussions that would ultimately contribute to what became the First Step Act, President Trump’s law, which received wide bi-partison support and significantly influenced the federal Bureau of Prisons. At the same time, Shon pursued and achieved a tenure-track position at Georgetown Law.
His rise was extraordinary. Unfortunately, his story took a tragic turn.
Authorities accused Shon of committing crimes related to domestic violence. Additional charges followed concerning how he responded. A jury convicted him. Prosecutors have publicly stated that they are seeking a lengthy sentence.
I do not know the facts beyond what has been publicly reported. I cannot speak to the details of his case.
But I can speak to the broader lesson.
The Weight of Collateral Consequences
When someone with a criminal history rises to public prominence, the stakes become higher.
The public memory of a conviction never disappears. It may fade. It may soften. But it does not vanish. For someone who achieves professional success after prison, scrutiny intensifies, which amplifies the fall if that person falters.
This is one of the harsh realities of collateral consequences.
A person may serve a sentence.
A person may earn degrees.
A person may build a career.
But the past remains part of the narrative.
That reality does not mean people cannot change. Shon’s life demonstrated that change is possible. He went from armed bank robberies to writing briefs that led to victories in the U.S. Supreme Court. He became a law professor, a husband, a father, and an advocate for reform.
But transformation requires ongoing discipline.
Substance abuse, emotional instability, untreated trauma—these do not disappear simply because someone achieves professional success. If a person struggles with addiction while incarcerated and does not resolve it, the risk of relapse intensifies after release.
Success can mask unresolved vulnerabilities.
Prison Professors does not sugarcoat this truth. We teach that preparation must extend beyond résumé building. It must include emotional maturity, accountability, and long-term personal stability.
Advocacy and High Standards
People who advocate for reform often live under a microscope.
If they stumble, critics may not simply condemn the conduct—they may question the entire reform movement. That is another collateral consequence of public success after prison.
Those who work to expand opportunities for formerly incarcerated people, Shon’s situation is deeply saddening. Rather than a single event, redemption requires lifelong commitment.
Shon’s story—both the rise and the fall—remains instructive.
It shows:
That transformation is possible.
That the law can change.
That society benefits when we incentivize the pursuit of excellence.
And that unresolved personal issues can undo years of progress.
Prison Professors exists to help people build sustainable change—not temporary elevation.
We encourage:
Ongoing self-reflection.
Honest documentation.
Treatment when necessary.
Long-term discipline.
Collateral consequences do not disappear because someone succeeds. They recede only when sustained effort and stability support the new narrative.
Shon illustrated the power of perseverance. His recent challenges remind us that perseverance must continue.
We will continue teaching the strategies that helped many people overcome immense obstacles. And we will continue acknowledging the complexity of the journey.