SEPTEMBER 20, 2005

I swung my legs out from under the thin cotton blanket and rested my feet on the cold concrete floor. In the early morning hours, my cellblock remained still and dark. Despite the weariness permeating my bones, I’d barely slept at all.

This was it—Judgment Day.

The Santa Rita Jail in Dublin, California, had confined me for the past nine months, but by the end of the day, I would know whether I was leaving jail at last or doomed to a federal prison for decades to come.

I stood up slowly and pulled out my prison uniform. For appearance in federal court, I had the right to dress in normal clothing, but whatever normal clothes I was wearing the day of my arrest had gotten lost inside the county system, so I had no civilian clothes at all. The best I could do was a clean, ironed, white T-shirt that José, one of the jail trustees, had secured for me from the laundry, a pair of red scrub pants, and shower shoes I’d been given during intake.

Santa Rita Jail in Alameda County is an enormous facility that houses more than four thousand inmates—typically convicted felons sentenced to county jail or those still awaiting arraignment, trial, or sentencing. The men in our maximum-security pod were under protective custody and segregated from the general population. Our group of inmates included informants, gays, transgendered women, and horny straight guys who wanted an easier stay—all rather harmless people at risk of being killed or maimed by the violent felons and gang lords on the other side.

Our pod also kept federal holds—guys like me facing prison time for federal crimes. My list of charges included possession of controlled substances, conspiracy to commit credit card fraud, fraud and related activity, possession of stolen mail, and possession of stolen identities—all of it the racket my then-boyfriend, Richard, and I had used to fund our relentless drug habit. Addiction owned me then, mind, body, and spirit. I wholly and completely belonged to the oblivion. As a result, I’d spent nearly a year in this hellhole with the possibility of many more to come.

Cleaned up and dressed, I sat tensely on the edge of the metal bunk bed, my hands clasped and my gaze down, when the cell door buzzed. The sound jolted me like a bolt of electricity. The next thing I heard was the deputy calling my name. It was time to go.

The deputies entered my cell to cuff my hands and shackle my ankles for the transport to the federal courthouse in San Francisco. Hindered by the restraints, I could only shuffle between two guards out of my cell and through the ward. The cellblock had begun to come to life, but the other inmates, still drowsy from sleep and knowing where I was headed, spoke few words, mostly just offering a nod or a look that meant good luck. Tamica, one of the transgender women, yelled out, “Miss David!” I usually hated being called that, but she said it with love, and I needed to hear it that morning. “You gonna be fine—don’t worry,” she said, waving. 

Outside, the transport unit, a motor coach with different sections of interior caging, stood ready to receive the line of us en route to court. The guards placed me in a seat within the locked cage for prisoners in protective custody before unshackling my arms and legs. I rubbed my wrists and stared through the tinted windows, seeing nothing. I thought back to earlier conversations with my defense attorney, Nina Wilder.

When I last saw her, Nina had asked me to be patient while the prosecution built their case. For much of my time in Santa Rita, I’d had little communication from Nina or anyone in the court system—no dates, no guidance, no news from the outside world. I had written letter after letter to the court asking for even one iota of a clue as to what to expect. It wasn’t until August that I finally had my plea arraignment, in which I agreed to plead guilty to one charge so the prosecution would drop the rest. But the morning of my sentencing, I had no idea what to expect. The stress of not knowing made me crazy.

On the bus across from me sat another federal prisoner, a handsome, muscular black man named Marius who had been busted with ten grams of speed. He too was headed for a sentencing hearing, but unlike me, he remained calm and at ease.

“Yeah, my baby mama gonna hit me up with some cash on the books, and I’ll do my thirty-six months and be outta there,” he bragged.

I didn’t know how many baby mamas he had, but even in his yellow jailhouse clothes, he was so sexy he could have had any baby mama he wanted.

Given the sentencing guidelines for drug possession with intent to distribute methamphetamines, Marius was looking at three to ten years. He had a girlfriend and a baby and a life on the outside, so he trusted he would get a lenient sentence. I wished I shared his confidence. Maximum sentences on the combined total of my charges added up to fifty-five years, though my plea deal reduced the probable jail time to something between three and ten years like Marius’s case. I could barely tolerate the thought of even one more day in that jail, let alone a decade.

After the forty-mile ride into the city, our transport unit pulled into a parking garage beneath the Phillip Burton Federal Building and US Courthouse. The monolithic concrete and glass structure runs the length of a city block on Golden Gate Avenue in the heart of San Francisco’s Civic Center. One by one, we submitted our hands and feet back into the shackles and descended from the bus.

Fear coursed through my veins and rattled my bones. I felt weak, and the weight of exhaustion bore down on my whole body. I found myself in almost constant prayer to a god I barely believed in. Beyond a miracle, what hope did I have left? The only thing that consoled me was knowing one way or another, the waiting would be over. After such a long, harsh battle, the closure would bring a measure of relief, even as I dreaded the possibility of being locked indefinitely in a human cage.

A team of deputies led us through a system of tunnels, hallways, and secure elevators until we arrived at a large holding area on an upper floor of the courthouse. I waited there until my name was called again, and then a guard escorted me down to a smaller holding cell outside of my judge’s courtroom. The cement cell had no windows—just an entry door and a side door that led to a glass conference room where inmates could meet with their attorneys in advance of their hearing.

In my holding cell sat four other guys, including Marius, all of us slouched on cold metal benches bolted to the wall. I stared at the floor, trying to piece together the years of my life and series of decisions that had led me to this place. I shook my head in disbelief that this was what I had become. If only I could start over again, do a few things differently—but it felt useless to hope or dream. The flood of stress and confusion overwhelmed me. I kept my thoughts centered on whatever I could. I needed to keep my wits about me—today was no day to fall apart.

When Marius’s case got called, I straightened up a bit and nodded at him. He smiled and gave a thumbs-up before following the bailiff out of the cell.

I wondered how he would fare in his hearing. This was no county courthouse. This was a federal institution where everyone dressed in their Sunday best on a daily basis to appear before the judge. And this was no low-level magistrate either. Inside the courtroom presided a stern district judge named Phyllis J. Hamilton who had been appointed by President Bill Clinton and made famous for her controversial decision to strike down the Partial Birth Abortion Ban Act earlier that year. She followed the rules. Her court went by the book. That’s just how it was.

While I waited, Nina appeared at the glass side door; she was a small but fierce Jewish woman who spoke straight and sharp. I exhaled loudly when I saw her. She motioned for me to join her in the conference room next to the holding cell.

“David, you have to stop writing letters to the court! You’re not helping your case,” she said, straightening a stack of papers on the table. After a brief reminder of the plea deal she’d worked out with the prosecutors, she continued, “Listen, I have no idea what’s going to happen. This could go in any direction. We don’t even know what kind of mood the judge is in today. Just don’t expect any mercy. And don’t you dare go in there and talk about how you found God.”

After a bit of coaching on what I should say to Judge Hamilton, Nina released me, and I returned to my spot in the holding cell. I was staring at the ceiling, rehearsing my prepared speech, when Marius returned from his hearing.

The moment he entered the cell, the outcome was evident; his face revealed his devastation. He rushed to the corner, fell to his knees before the toilet, and threw up. When he finished, he slouched against the wall, exhausted and nearly catatonic. He’d gotten eight years, nearly a year for every gram he’d had in his possession, and he would have to serve 85 percent of that time, no matter what. The federal system had no good-behavior program, and though there were ways to get a sentence reduced or be granted an exception, such motions were extremely rare.

Marius shook his head slowly back and forth. The justice system isn’t kind to people of color, especially black men, who are routinely sentenced more harshly than any other demographic—a horrid fact of our system. For Marius, this fact was his new reality. We chatted a bit, making small talk to distract him from the world crashing down around him. He was still recovering from the blow when a deputy buzzed the door to take him back upstairs.

After his sentencing, I could barely breathe. He had been so confident he wouldn’t get sentenced harshly, but he did. I couldn’t conceive of spending eight years on the inside. I wasn’t confident at all about my chances before this judge. Even as a white man without an extensive criminal record, I couldn’t predict what would happen in the federal system. No one, not even my attorney, had been able to discern what would happen in my case. The judge might be lenient and give me the lesser sentence, or she might decide to make an example of me to deter other white-collar criminals. After what she had handed to this guy, my last ounce of hope dissipated altogether. I was fully convinced she was going to send me away.

My case wasn’t called until late in the day. When the door clicked and the bailiff finally said my name, I nearly jumped out of my skin. This was it. I took a deep breath and stood up to go. No matter what happened in the next few minutes, I knew only one thing for sure—my life was never, ever going to be the same again.