Justice Notes: The Letter
A White-Collar Journal forum for criminal justice, lived experience, and the personal search for redemption
Since my release, I have often thought about writing a letter to Judge Bolden, the presiding judge at my sentencing. I was deeply moved by the fairness and humanity of his deliberations, which I only fully appreciated later when I read the transcript.
For legal reasons — and because it’s generally considered improper by the Department of Justice — I never sent the letter. But the words have stayed with me, and so I’ve decided to publish them here, precisely as I drafted them at the time.
What follows is not just a letter to a judge but a document of reflection: an attempt to reconcile shame, conscience, and the hope that writing might become a path toward meaning.
AN OPEN LETTER TO THE JUDGE
A Case For The Judiciary
Dear Judge Bolden:
At my sentencing hearing, you provided a compelling narrative before my sentencing. Unfortunately, the acoustics were such that I was unable to hear them. Also, I was overwhelmed by the circumstances and traumatized by the proceedings: the comments by my investors, the depiction of me by them and the prosecutor, the embarrassment of all of the revelations in front of my family, closest friends, and others, and just the realization of being a defendant in a courtroom where I never imagined I would find myself, at least not in my earlier years. In the year leading up to that day, its prospect was a daily nightmare. The only part of your remarks that I heard was the amount of time that I was sentenced. I’m sure almost every defendant, after being called to rise, experiences the same fog of the brain, the blur to everything going on, legs trembling, barely able to stand up, and incapable of processing anything other than the number at the end.
I read your comments only recently, while writing a memoir about my experience and researching the court documents related to my case. I was overwhelmed by their breadth, the depth of your deliberations, the comprehensive review of my biography to fairly measure the character and substance of defendant John DiMenna with authentic, detailed reference to letters and comments by others, and the struggle to balance that with the responsibility of your office and the burden of its agency. I’m not sure I deserved it. But I have been incredibly moved by it. One assumes that the profile of the judiciary is an institution comprised of one-dimensional scholars, driven only by tedious texts, absent nuance and humanity, indeed not in consideration of the “inner spirit”, the “invisible bars,” or the search for the “soul.” I still have significant questions about my own. None of them has led to anything that I can feel better about, yet. It’s difficult at my age, especially when you realize that there are no comebacks in the cards and no opportunity for meaningful restitution and redemption. There’s not enough time to practically implement anything to make amends. Plus, at such an advanced age, the years of regret overwhelm even the most perfect of the few remaining. And in prison, it’s even harder to do that. In prison, there is nothing to ground you. That’s probably why many join Bible groups and other paths like that. Some experience an epiphany of sorts. They dwell in the sunlight of the epiphany for a time. Still, eventually, it dissipates in the gloom of everyday prison life.
For me, it was a return to writing that presented a possible path. I aspired to be a writer in college and always believed that I’d return to it at some point. I decided that my incarceration would provide that opportunity, and I began writing the first day I arrived. It helped me get through the trauma of the arrival and the processing that an inmate endures, especially at Devens, where all new inmates are placed in Solitary confinement for three days in the main prison. Even as I was overwhelmed by it, I kept telling myself that all that I was experiencing would be material for my writing. And no matter how terrible it might be, whatever loomed ahead would benefit and provide me with the empathy I would require to create meaningful writing and find personal growth. And that got me through those early days.
Maintaining the effort was not easy. Unfortunately, the infrastructure at Devens made it challenging to write consistently. But I was able to complete a collection of sorts that became the basis of the manuscript I’m writing. I am precluded from returning to business, and I believe that is a blessing. I can devote myself full-time to writing. The writing I referenced is a memoir based on my experience. It is a hybrid work, much of it comprised of poems and log verse compiled during my time in prison. I'm sharing three of the poems here to demonstrate (hopefully) to you my growth. I don’t know if I have or if I will accomplish that. But I am trying.
At the close of my hearing, you shook my hand. I didn’t understand then. But I think I do now. It was to reconnect me to humanity. I may have been branded a felon, but I should not give up on myself, and that a return to community is possible. I did seek out therapy, before and after my incarceration, to try to understand my behavior or, at the very least, provide some context. I believed that I am a person of conscience. I’m still hopeful that it is the case. My therapist said that most of my conduct is based on a lifelong pathological fear of confrontation that resulted in a pathological pattern of coping strategies that led to my illegal activity. Subtext: I was a coward. I do believe that my greatest crime, or at least the driving force of my crimes, was fear rather than malevolence. Not that I’m off the hook by any measure. It’s of no solace to me, and certainly not to my investors. I was just unable to confront whatever was in front of me and always opted to manufacture an alternative reality, to the detriment of everyone involved. I’d been doing it all my life. And it worked until it didn’t: the strategies escalating to more and more outrageous activity until the final accumulation of all of my machinations and schemes eventually blew up everything and everyone in my path. That’s a revelation almost impossible to bear for a person of conscience.
My life is essentially behind me. I cannot go back, obviously. But during what time I have left, I will, as my pastor at Marble Collegiate Church has suggested: “…stop chasing the wrong things that have cursed us, so that the good things can catch up to us.” Hopefully, my writing will be the medium for that process to play out. I’m encouraged by the progress of my memoir. I hope that the final manuscript will be a worthwhile and enlightening document that can benefit others. Perhaps it will prove worthy of the potential that my creative writing teachers saw in me almost fifty-odd years ago. Maybe that was the turning point for me when I chose to leave that world behind. But there are no redo’s in life. So many accused today of some malfeasance resort to the same response: “That is not who I am,” as if what has happened doesn’t matter. Bill Parcells, a football coach, said, “You are what your record says you are.” And I believe that is so, in life, as well as football. In the future, I hope that I will have enough time, persistence, and determination to be able to become my best self, a person of conscience, and to say, at least to myself: “THIS is who I am.”
Thank you again for my release. I am confident that my conduct going forward will not cause you ever to regret that decision. And finally, of all of the people I have impacted and deceived, my shame will never leave me. That is the nexus of the invisible bars you reference at my hearing, which are the subject of my memoir and continue today, even as I sign this letter. And maybe that’s a good thing.
Sincerely,
John J. DiMenna, Jr.
Closing Note
Publishing this letter now, years after it was drafted, feels like a way of honoring the process I’ve been through. It’s less about seeking a response from Judge Bolden than about testifying to the struggle of reckoning with one’s past.
For me, writing has been both a mirror and a lifeline: a means of recording the shame, the questions, and the moments of clarity that came in the aftermath of incarceration. If nothing else, this letter reminds me that even when restitution is impossible and forgiveness uncertain, the act of naming the truth still matters. That, I’ve learned, is its own form of justice.
If this piece resonated with you, consider sharing it or leaving a comment. To support this work and help spread awareness about justice reform for white-collar defendants, subscribe to White-Collar Journal and stay connected. John DiMenna is a member of the White Collar Support Group.
To leave a comment, Substack may ask you to verify your email address (a one-time step to prevent spam). You don’t need to subscribe or create an account. Just check your inbox for a one-time link.

