"A FELON FRIENDSHIP"

My friendship with Jesse Jackson, Jr. and what we hope to achieve together; to help more than 20 million non-violent felons regain their dignity and lives!

Today, I want to step away from the usual cynicism and focus on something that I don’t often feel in these times—hope. Yes, you heard that right. Hope."

"Now, before you roll your eyes or think I’ve lost my edge, let me explain. In the wake of Donald Trump’s stunning victory in the 2024 election, it would be easy to slip into despair, especially for those of us who’ve spent years fighting against his brand of divisive rhetoric and autocratic tendencies. And while there’s plenty to critique, today, I want to focus on the opportunities that lie ahead. Because, believe it or not, every administration—yes, even a Trump administration—has the potential to do good, to right wrongs, and to uplift those who’ve been left behind. It’s up to us to hold them accountable and push them to deliver."

"That brings me to today’s guest, someone whose story embodies resilience, redemption, and the fight for justice—former Congressman Jesse Jackson Jr. For those of you who know the Jackson name, it’s synonymous with the civil rights movement, with courage in the face of adversity, and with an unwavering commitment to justice. Jesse Jr. carried that torch into Congress, championing initiatives to uplift marginalized communities, fight systemic inequities, and create a better future for all Americans. But, like so many of us, his path hasn’t been without its stumbles."

"Jesse’s legal troubles and subsequent incarceration were a stark reminder of how even the most promising careers can be derailed by personal and systemic challenges. Yet, what stands out about Jesse isn’t the fall—it’s the rise. It’s the way he’s used his experiences to advocate for criminal justice reform and to shine a light on the barriers that so many former felons face when trying to rebuild their lives. In Jesse’s story, we see not just the pain of injustice but the potential for change."

"And let’s be clear: criminal justice reform isn’t just a buzzword or a campaign talking point—it’s a moral imperative. For decades, our system has disproportionately targeted and punished Black and brown communities, perpetuating cycles of poverty, disenfranchisement, and despair. The statistics are staggering: while Black Americans make up about 13% of the population, they account for nearly 40% of the incarcerated population. That’s not justice—that’s systemic failure."

"Jesse Jackson Jr. understands this deeply, not just from his own experiences but from the countless stories of others who’ve been trapped in this broken system. And he’s here to talk about solutions—about the urgent need to restore voting rights to non-violent felons, about creating pathways for reentry into society, and about dismantling the policies that have criminalized poverty and addiction. These aren’t just political issues; they’re human issues."

"But the fight doesn’t stop there. Uplifting marginalized Black communities requires more than reforming the justice system—it requires a comprehensive approach that tackles education, economic empowerment, healthcare, and housing. It means addressing the root causes of inequality, not just the symptoms. And yes, it means holding the Trump administration’s feet to the fire, demanding that they go beyond the hollow platitudes and actually deliver results."

"Here’s the thing: I’ve spent enough time around Donald Trump to know that his priorities often don’t align with the needs of everyday Americans, let alone those who’ve been historically marginalized. But I also know that pressure works. Public outcry works. And as cynical as I can be, I believe there’s a chance—however slim—that this administration might surprise us. Maybe, just maybe, they’ll recognize the urgency of these issues and take meaningful action. If not, it’s up to us—activists, advocates, voters—to make sure they do."

"Today, Jesse and I are going to dive into these topics and more. We’ll talk about his time in Congress, the lessons he’s learned from his own struggles, and his vision for a more just and equitable future. We’ll explore what it means to carry the weight of a historic legacy and how he’s using that legacy to fight for those who need it most. And, of course, we’ll ask the tough questions about where we go from here—because while hope is important, action is essential."

This is going to be a conversation you don’t want to miss. Jesse Jackson Jr. is a man who’s lived through the highs and the lows, who’s seen the best and worst of our justice system, and who’s come out the other side with a renewed commitment to making a difference. And in a world that often feels like it’s teetering on the brink, his story reminds us that redemption is possible, that change is possible, and that hope—against all odds—still matters."

So let's go now to that conversation.

And now for today's Mea Culpa:

When I reflect on my own journey—from a lawyer in Donald Trump’s world to someone convicted of crimes and serving time—I can’t help but think about how my life intersected with Jesse Jackson Jr.'s. On the surface, it might seem that Jesse and I come from completely different worlds. I spent years as Trump’s personal fixer, deeply entangled in political machinations, while Jesse grew up with the legacy of his father, Reverend Jesse Jackson, and became a Congressman with a vision rooted in service to the marginalized, the oppressed, and the voiceless. But despite the stark differences in our professional lives and backgrounds, there’s an undeniable connection between us—one forged through the crucible of accountability and the painful but transformative experience of redemption.

I’ll admit, it wasn’t until I found myself at my lowest point—facing the legal consequences of my actions—that I began to understand what true accountability means. It’s not just about admitting you did something wrong; it’s about confronting the full extent of the harm you've caused, facing the punishment, and, most importantly, using that painful experience to drive change. For me, that meant speaking out against the very system I helped perpetuate, fighting for transparency, and advocating for reform. And, in many ways, Jesse’s journey mirrors my own in the most unexpected ways.

Jesse, like me, fell from grace. He was convicted of misusing campaign funds, and his political career was brought to a halt. But what I admire about Jesse is how he used this moment of failure to look inward, take responsibility, and focus on the bigger picture. His experience with the criminal justice system—and how it treated him and others—led him to become an advocate for reform, particularly for nonviolent offenders. He championed causes like restoring voting rights for former felons and ensuring that those who have paid their debt to society have the opportunity to rebuild their lives.

In many ways, Jesse’s story is about redemption, not just for himself but for an entire system that has failed so many people. He’s shown me that accountability isn’t just about personal growth; it’s about using the pain of one’s mistakes to advocate for the voiceless. And that’s something I deeply relate to. My own transformation, after all, is not just about healing myself but also about standing up for those who continue to suffer from the injustices I once enabled.

Now, as I look at our paths side by side, it’s clear that, although our professional lives have been very different, our experiences of fallibility and redemption have been remarkably similar. We both know the agony of losing everything. We both understand the weight of public shame, the humiliation of knowing that the very people you once served now view you with distrust. But more importantly, we both know what it means to rebuild from the ashes of those mistakes.

The key here is not that we fell—we all fall. The key is what we do after the fall. For Jesse and me, the answer was to get up, take responsibility, and work to change the systems that led us to the places we found ourselves. I believe that’s the power of accountability: it forces us to not only reflect on our actions but to use our voices for good.

What has struck me most about Jesse’s journey is the way he has turned his experience into a call for justice—particularly for marginalized communities. As someone who experienced the flaws of the criminal justice system firsthand, Jesse has worked tirelessly to fight for others who are caught in the same system, often through no fault of their own. He’s shown that, despite the pain of personal failure, there is power in using your story to help others.

For me, this shared experience of accountability and redemption is a reminder that, while we may have walked different paths, we are united in our belief that change is possible—both for ourselves and for the systems that we once participated in. The truth is, Jesse and I have more in common than I ever could have imagined when I first set foot on this journey. Both of us understand the weight of our past mistakes, but we also understand the weight of our responsibility to ensure that our future work contributes to a more just and equitable world.

So, as we continue to advocate for criminal justice reform and work to uplift marginalized communities, I’m reminded that redemption isn’t just a personal journey—it’s a collective one. Jesse and I may have different stories, but our shared commitment to accountability, reform, and advocacy for justice ties us together in ways that transcend our differences. And that, ultimately, is what gives me hope for the future—that despite our pasts, we can work together to create a better world for those who have been left behind.

And as always, thanks for listening.