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39 Years

I rejected a plea deal and chose instead to go to trial. I would not understand until too late that I had placed a target on my back.

Shebri Dillon header2
The calling to speak is often the vocation of agony.
—Martin Luther King, Jr.

They, them, theirs. All terms for the collective whole of actors who make up the criminal legal system. No one person is solely responsible; that is not by accident. They are able to sleep at night because the collective is responsible for any damage caused.

They amplify our shame. They refuse to acknowledge our humanity. They count on us not being able to untangle the knots. They isolate and degrade us, caging our bodies and attempting to cage our minds. They count on our silence.

But I will speak.


I am a single mom of four amazing children. In 2015 I was working full time as a bartender to support them, and to avoid missing important daytime school events. Money was tight, but we were making it.

Due to our fragile financial balancing act, I took a friend up on an offer to move in. It would ease both our bills to share household expenses. It also meant my children would be in a better school system. The friend was in the middle of a divorce and asked if I would be willing to serve as his power of attorney. In addition to the divorce, he was facing some unspecified legal battles; he was vague, but I said yes.

Then I learned the horrifying truth about his legal battles: soon enough, he was arrested and charged with molesting my goddaughter.

When he was given just a year in jail, I came unglued. I took justice into my own hands.

I had learned from my goddaughter that he had promised to gift her his trailer home if she stayed quiet about what he had done. So I gave his important personal effects to his cousin, put the rest in storage, and sold the trailer with the land it was on, making sure he would never be able to use those things to lure a child ever again. Per my responsibility as power of attorney, I used the proceeds from the sale to pay off his debts, left him a few grand in his bank account, and then cut up the credit card he had given me. With what remained of the money, I relocated myself and the children.

That’s how my legal troubles started.


Before I go any further, I must shatter your perceptions about this system that I’m caught in.

We are taught as little children that the criminal justice system is about morals—right and wrong. I continued to believe this, right up until I became meat for the beast. Now I can say with absolute confidence that the system is not about moral integrity. Its outcome is almost entirely shaped by a defendant’s socioeconomic status and clout.

I am often in the unfortunate position of having to tell shell-shocked, newly incarcerated women that the system doesn’t care about the moral wrong they have suffered at its hands. I explain that applying morals to their conviction process is like trying to apply morals to a football game. You cannot watch a tackle and decide the moral value of it. You review it to see if it violated the rules. There is no other way to throw a flag on the play. It is the same with the criminal legal system.

But we are told it is something different, and so many of us believe it. It is this belief that was the beginning of my demise.


I was charged with forgery initially, a baffling charge: I had power of attorney for him, which includes the legal right to sign for him. The judge was no less baffled and threw the case out. Dismissed.

I would not understand until it was too late that my success in court had placed a target on my back. When I left the courtroom relieved, thinking it was over, the prosecutor had left feeling humiliated. Causing that humiliation was, in the end, my greatest offense—far worse than any crime I’d allegedly committed—and I would suffer for it.

Months later, I was indicted for fifteen felonies. Taken together, they didn’t even add up to a coherent narrative. Had I simply overrun the scope of my role as power of attorney? Or had I committed outright theft without the man’s permission or knowledge? Both, apparently. It was a move I would, once I was incarcerated, come to understand as an extreme example of charge stacking. This is a common practice by which a prosecutor redundantly, massively overcharges to gain maximum leverage against a defendant who may now be facing literal lifetimes of prison time, even for a relatively minor offense. The prosecutor also undertook other actions to enhance the vast power he held over me: He made certain that my case was placed in front of a different judge—one notorious for his harshness—and saw to it that I was assigned to a less seasoned public defender than I’d had the first go around.

The prosecutor thus made me start from scratch while he stacked the deck. I was not a human being involved in a practice of societal accountability; I was an opponent in a game I didn’t even understand, let alone know how to win.

That game extended beyond the courtroom, right into my own home. After I had already been indicted, appointed counsel, and given a court date, a search warrant was executed at my home for the original documents. I had been cooperative and completely nonviolent, yet police entered my home with guns drawn, aiming them at me and my children. My children were then separated from me while I was cuffed and questioned without counsel. I was threatened that if I didn’t cooperate I would lose my precious babies. When they couldn’t find the documents on their own, they uncuffed me and I simply handed them over, as I would have done from the beginning if they had just asked. My entire family was scarred.

After the police had stormed my house, the prosecutor offered me a deal. He wanted me to plead guilty to all fifteen felonies, even though some contradicted one another. In exchange he would recommend that I be sentenced to between one day and six months of jail time. I had no prior convictions—nothing that would require an “enhanced” (longer) sentence. According to the personal sentencing guidelines that the prosecutor’s office gave me when proposing the plea deal, the crime didn’t merit a sentence longer than that. I did not yet understand that there was a difference between personal sentencing guidelines and legislative guidelines, much less unspoken rules about how and when each were applied.

At the time, this left me confused. Why would I plead guilty to all of these charges, when the sentence I would receive for doing so was no different than what the prosecutor would seek anyway were I found to be guilty? I didn’t even know what half of the charges meant, and I sure wasn’t guilty of a large chunk of them.

So I said no; I refused the plea deal.

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I figured I would take my chances in court. It didn’t seem that I had anything to lose. I plead guilty, I go to jail for a day to six months; I’m found guilty, I go to jail for a day to six months.

I did not understand that declining a plea deal—exercising one’s constitutional right to trial—is among the gravest off-the-books crimes a defendant can commit, punishable by more than I would have ever imagined. No one had explained to me that as soon as I went to trial, my personal sentencing guidelines went up in smoke. The sentence the prosecutor now sought was the sum total of the maximum sentences for each and every one of the fifteen felonies—in effect a life sentence. For example, the legislative guidelines allowed for a maximum of twenty years for the single grand larceny count, another twenty for the lone obtaining money count, and yet another twenty for money laundering (a charge which still makes no sense to me). The other offenses had a range of maximums of less than ten years. It all added up to certain death of my life as I knew it.

There were so many things that I had not known—could never have been expected to know. I did not know that the jury would not be told about my lack of criminal history, nor given any context about how rare it is for members of the community to be sentenced heavily for similar offenses. I did not know that, at the time, Virginia was an outlier nationally in how it sentenced: juries actually recommended sentences—and were, worse yet, allowed to be given misleading guidance by officers of the court. That is, they were told that their sentences were only a recommendation and that the judge would use his superior knowledge—of context, proportionality, criminal history, and so much more—to make an informed decision about what the specific case merited. In reality, however, judges tended at the time to defer to juries’ sentencing recommendations. It created a perfect storm in which everyone was left feeling as though they bore little responsibility for the finality of their damnation.

Some years after my conviction, Virginia ended jury sentencing because of the severity of the sentences it produced. But I didn’t need to be told that. I knew firsthand by then.


When I walked into the courtroom, I knew none of this. I still believed in the moral integrity of the prosecutor and of the system itself.

It quickly became apparent to me that I was in trouble. My newly appointed attorney had failed to prepare for my case at all. He promised the jury all kinds of facts and proof he never delivered. He threw unprepared witnesses on the stand. (I knew in some cases that witnesses had only been subpoenaed the night before because my attorney had made me deliver the summons to them myself.) None of my evidence was ever presented, and my attorney told me that if I took the stand, I would lose my right to appeal. That is untrue. He would, in fact, be disbarred a few years later, having amassed too many reports of gross incompetence for the court to continue looking the other way. But he was never held accountable for what happened in my case.

In the courtroom, I was, quite simply, on my own.

In the end the jury convicted me of ten of the prosecution’s fifteen counts. Some of the convictions even conflicted with one another. I was too poleaxed to realize it at the time, and if my attorney did, he did nothing about it.


When a defendant is found guilty in court, a separate sentencing phase of the trial commences. In the sentencing phase of my trial, the prosecutor—the same prosecutor who had offered me as little as a single day in jail, and no more than six months—faced the jury and told them that I posed such a great danger to society that they should sentence me to seventy-three years in prison.

Even my ineffective public defender gasped audibly.

But the prosecutor wasn’t done punishing me for my off-the-books offense of daring to refuse to plead guilty and invoking my so-called “right” to a jury trial. I recall the prosecutor going on to tell the jury that I was as “brazen as any criminal” he had ever seen, and that I should be sentenced severely as a deterrent to others who might be tempted to commit real estate and property crime, like mob bosses and drug kingpins. He knew full well that I had no involvement in such things.

The jury did not give me the seventy-three years that the prosecutor requested. They sentenced me to half of that: thirty-nine years. I still do not believe they understood the finality of their recommendation in those moments. I sure didn’t.

I was still functioning under the misconception that the original sentencing guidelines that had been presented to me—one day to six months—would be what the judge would work from. Sure, I was stunned by the tone that the prosecutor had taken in the courtroom—but it never occurred to me that my personal sentencing guidelines would be irrelevant in the judge’s decision-making.

My confusion prompted a concerned friend of mine who’d previously had some legal trouble to attend my next meeting with the public defender. We asked him to explain to us what was going on, and he informed us, obliquely, that my guidelines had changed. This made no sense to us, and my experienced friend recommended I seek other counsel.

I randomly picked a local attorney from the phone book and scheduled a free preliminary consultation with him. When we met, the attorney stated it plainly: I was facing all thirty-nine years the jury had sentenced me to. And I would be formally sentenced in a month.

Upon hearing the news, my friends got together and raised a few thousand dollars to hire that attorney to get me through the sentencing hearing. It was so late in the process, however, that there wasn’t much the attorney could do. He was able to delay the sentencing by a few months. But he was not able to save me or prevent the fracturing of my little family.

Attending my sentencing—looking straight down the barrel of a thirty-nine-year sentence—was the equivalent of attending my own funeral. My character witnesses begged for my life and it sounded like they were eulogizing me. We all knew by that point that my life as we knew it was at its end.

Like so many others before him, the judge excused himself of any accountability, stating that it was only right that, as an act of public service, he carry out the recommendations of the jury. He sentenced me to all thirty-nine years with no time suspended. He then laid out the specifics: ten years for one count of grand larceny, ten years for one count of money laundering, and ten years for one count of obtaining money by false pretense, to be served consecutively. In an act some might call mercy, he determined that for the remaining seven convictions, he would assign nine years that would run concurrently with the other thirty.

This left me with an active thirty-year sentence for nonviolent offenses, as a first-time offender.

The new attorney I had hired called this a win.

The prosecutor called it justice.

The judge called it a day.

I was at a loss for words.

The ramifications of having wounded the prosecutor’s ego didn’t end there. In the Virginia Department of Corrections, anyone with a sentence of twenty years or more is an automatic security level three, the same classification as a murderer. It didn’t matter that I was nonviolent, that I had no criminal history, that I worked even while inside. Until my remaining sentence dipped below twenty years, I would be housed in the maximum-security prison for women under severe security restrictions.

This meant that I would live out the next seven years of my life in a rectangle, surrounded by triple fencing topped with layers of razor wire, breaking bread with some of the most notorious women in the state—them and the live roaches that were served with the food on our trays. Extensive searches of our rooms, pockets, and naked bodies were routine. Housing units were designed so that we could be viewed like fish in a bowl. The lights never went all the way out. Ever.

I was not allowed to touch my children during visits except for a quick hug at the start and finish. The simplest things were considered serious contraband, such as tape, yarn, stickers, and pictures hung on the wall. Demands and orders were issued in such colorful and degrading language that fire blew through me. Undeserved, gut-wrenching, inhumane treatment sparked and turned inferno in my soul.

Security level three of hell.


With no resources to draw on and extremely limited time to make a plan, it was impossible to find anyone who was able to take in all four of my children. There was no choice but to split them up. Only the youngest two stayed together.

The fracturing of my family was the absolute worst part. Eight years later, it is still what sears my soul the most. More than missing a soft bed, a fork, a bath, quiet, privacy, and even safety, I miss tucking my children into bed at night. I miss dancing with them around the kitchen while making breakfast, singing “Lean on Me” at the tops of our lungs. I miss lullabies, school pictures, and watching them grow. I miss seeing their reactions to holidays, and every sports game and theater performance I haven’t been able to go to. I missed their graduations, attending them by phone in twenty-minute intervals.

They were punished, too. They are still being punished.

I continue to be amazed that we live in a society where even a cup of hot coffee comes with cautionary warnings, yet I can walk into a courtroom with my liberty at stake and not get so much as a trustworthy guide. A pamphlet, a map, something. Anything.

Of course I appealed, my friends continuing to scrape together what they could to pay for a private lawyer. But even with his best efforts, he couldn’t save me. My public defender had preserved nothing from my trial and the private attorney didn’t even catch that I was convicted of contradictory crimes. I figured that out on my own years later. When I eventually asked him why he hadn’t caught that, I discovered that he didn’t even have an understanding of what some of my charges were for. He was as confused as the jury had been. Two years ago, he would lose his license to practice law, too, stemming from a case of misconduct. So much for my guides.

Like so many incarcerated people, I began from necessity to serve as my own legal representative. I filed writs of habeas corpus, drawing on my own limited understanding of the law, and was denied over and over, advancing through the levels of the court system. I have continued that journey, refining my arguments as I gained legal comprehension. I am now awaiting the decision of the United States Court of Appeals for the Fourth Circuit.

Simply put, this is the end of the road. Short of a miracle, I am still facing twelve more years inside. And that assumes that I don’t wrack up any disciplinary infractions that would cause me to lose the credits (what we call “good time”) that I have earned thus far. But that’s almost entirely down to luck: here, giving a crying person a hug is a punishable offense. The rules and their enforcement are arbitrary; the enforcers can be ruthless.

Most of this I cannot change. I must only endure. They prefer it that way. But what I can do is take accountability for my part, own my own faults and shortcomings, and place theirs squarely on their shoulders, where it belongs and where it is long overdue.

Image: Matthias Wagner / Unsplash