When New York City Is a Prison

A former prosecutor enters the flawed probation system he had once defended.

“Yo, B! We should go to the beach!” My friend Joyce pounced, nearly toppling her chair in the probation department waiting area. We were on the tenth floor of Manhattan Criminal Court, high above the subterranean hell known as central booking. It was a place I’d come to know well in recent months, first when I was arrested, and held while the police searched through my apartment, and later, on return visits upstairs, when prosecutors from the Manhattan District Attorney’s office repeatedly threatened to send me to jail. It was now November 29, 2012, seven months to the day of my original offense, and a 91-degree forecast from August looped on the big screen while the judge contemplated my fate. After ten years in the system, as a prosecutor, public defender, and corrections reform expert, I was finally getting a taste of life on the other side.

A month earlier, in October, I’d been convicted of nine criminal counts after a lengthy trial. Today, after much waiting and legal wrangling, the decisions concerning my future had been made and the judge ordered me to report upstairs to begin my sentence. For the next three years I would belong to the New York City Department of Probation. My DNA, biometrics, whereabouts, home addresses, employers, pay stubs—all of it.

Walter Starbuck, a character in Kurt Vonnegut’s Jailbird, once mused about the challenges of collecting ironies, and in this case they were accumulating faster than I could keep track of them. A former prosecutor who had sent countless people through this system sitting and waiting to go through it himself. The judge directing me to answer a probation officer’s questions, without an attorney or Miranda warnings to advise me that he could—and would—use my answers to enhance my sentence. The times I’d cited New York City’s probation department as a model for probation officials in Kentucky and Louisiana, without ever having observed my home city’s officers in action.

The minutes peeled off as our group of ten friends decreased in size in the waiting area. After 80 minutes, Joyce and I were the only ones left. Bored, I counted heads. The best numbers detailing who is on probation in America were from the Pew Center on the States. They’d found that one in 45 white people were under correctional control, mostly on probation and parole supervision. I’d always wondered if the numbers were off, especially for drug-related offenses, which we commit at equal or higher rates than other racial groups. I tallied five out of 25 white faces in the waiting area in Manhattan, so maybe New York City was no different than other cities. But they were transferring me to Brooklyn to be supervised; perhaps there would be more of us there?



“Sir, if I had any hair, I’d be scratching it,” the intake officer said to me, pointing to the chair opposite his desk.


“Well, I just can’t make it out in your paperwork. Why the judge put you on probation?” he asked

To insure the public safety by the rehabilitation of those convicted, [and] the promotion of their successful and productive reentry and reintegration into society. This was the language in New York Penal Law 1.05 (6), the section that prescribes the post-conviction supervision of criminal offenders. But that language wasn’t referenced at sentencing. The judge had used the terms arrogant, out of touch with reality, and in denial of an expensive education—all personal qualities that I possessed—rather than citing traditional sentencing factors such as the level of dangerousness posed to society, antisocial behaviors, and the number and severity of prior convictions.

“Yes, sir, the judge was pretty upset with me,” I explained to the intake officer.

“You need to report to the Brooklyn probation office for orientation on December 4,” he told me. “In the meantime you cannot travel, drink alcohol, or use drugs.”

“Wait, I’m of legal age. Are you telling me I can’t have a beer when I get home?”

“That’s what I’m telling you.”

I arrived in Brooklyn on the appointed day at the municipal building, across the street from Borough Hall. During orientation, two probation officers informed 15 or 16 other probationers and me that possession of marijuana, disorderly conduct, and other minor crimes had terminated a most fundamental right in our lives: All of us, regardless of the seriousness or level of our offense, were ordered to remain within the five boroughs at all times. Probation had turned New York City into an open-air prison.

A typical-sized line outside Brooklyn's municipal building for reporting visits. (Bobby Constantino)

“What if I get a job in New Jersey for the next day, which I often do at night?” a woman shot her hand up.

“You can’t go without getting permission,” one of the officers repeated.

“My mom is about to pass,” another new probationer said, “so does that mean I can’t get on a plane if she does?”

“Not without permission.”

Like most of my fellow probationers, I thought that permission would be a simple procedural work-around. We would punch requests into a valid evidence-based framework and it would spit out answers based on nature, urgency, and likelihood of promoting rehabilitation. Partying on a yacht on the Jersey Shore: no. Visiting dying family members: yes. After orientation, I wrote my name on my new assigned officer’s sign-in sheet and waited to request permission to travel to Massachusetts to spend Christmas with my family.

There were ten men and one woman in the waiting area. A few of them were slumped on the table, with their heads down. One man was leaving a message for his boss. “Sorry, I’m gonna be late today.” Sixty minutes passed, then 70. In the most recent probation profile, taken in 2007, whites represented 17 percent of New York City’s probation population, which is less than half the percentage of our representative population in the city. When you consider that we possess weapons and contraband at higher rates than other racial groups in New York City, our number seems low.


I followed my new supervising officer through a locked metal door, down a long hallway, and into her office. There were several verses of scripture posted on the walls, which I thought boded well for Christmastime with my family as I sat down opposite her.

“I need your proof of address and pay stubs,” she told me.

“Okay, I just emailed them to the intake officer in Manhattan. What is your email address and I will—”

“Excuse me. Did I ask you to email them to me?”

“I’m sorry?”

“If I want you to email something I will ask you to email it.”

We sat in silence while she typed on her computer.

“Okay, you need to come back in the week of your birthday and bring those documents to me in person. My reporting day is Thursday.”

“Okay. But that’s right before Christmas. I was hoping to ask you for permission to travel and visit my family—”


“I’m sorry?” I asked, confused.

“I said no.”

Multiple studies, including one that tracked 7,000 probationers, have shown that a strong offender-officer relationship is perhaps the single most important factor in determining whether probation supervision will achieve a positive public safety outcome.

On my second visit, after I spent Christmas in Brooklyn away from my family, I’d booked a role on a TV show that was scheduled to air on the History Channel in the spring. I’d been out of work for several months and my financial situation was deteriorating faster than I could keep up. The episode filmed on the day she asked me to report the following week, so I requested permission to report on a different day.

“No, you have to report on your assigned day.”

I pleaded with her. Explained how much I needed the money. I cited best practices materials from the Council on State Government, National Council of State Legislatures, and New York’s own guidelines. These resources, which I’d used often when working with probation departments in the past, provided comprehensive toolkits for effective supervision. They advised officers to be flexible with low-level offenders and to avoid placing onerous restrictions on them, as this increases the likelihood that they will reoffend. They encourage probationers spending time with family because healthy, prosocial relationships promote rehabilitation. They support allowing probationers to work so that they can reintegrate into the workforce and become productive members of society. Yet despite these directives, a nearly perfect, undefeated season of no’s continued: Easters, birthdays, Thanksgivings, baby showers, even funerals.

By April 2013, I’d been out of work five months, and I’d agreed with my landlord that it was time to move out of my apartment. I reported to my probation officer to explain the situation and to request permission to stay with family out of state until I could get back on my feet.

“I don’t have anything to do with that,” she told me.

Some will say that lawbreakers deserve this style of treatment, which is fine, but the law clearly says otherwise. The law says that rehabilitation is the best way to “insure the public safety,” and the best evidence out there shows that rehabilitation—something New York’s taxpayers give probation upwards of $300 million annually to accomplish—is squarely at odds with forcing probationers to miss work and other important life events. Such refusals pressure probationers that might normally abide by their conditions to instead go out and violate them. And sure enough there I was, in August 2013, speeding north through Connecticut like a fugitive in direct violation of my probation conditions.

Idene Wilkerson, or “Ma Siss” as everyone called her in the Dorchester neighborhood of Boston, was like a mother to me. “I may not have birthed you, but you belong to me,” she told me the night I met her in a chop shop she’d converted into a church on Quincy Street. She’d changed my life in every way, and I was traveling to Boston to pay my last respects. A few months earlier my request to attend a memorial for one of the victims of the Boston Marathon bombing, whose second grade class I’d visited several times and marched with once, had been denied, so I wasn’t asking this time around.

As I headed north on my way to Boston, I remembered how the judge had added a condition to my sentence which allowed probation and the NYPD to enter and search my residence anytime without a warrant. The week before my arrest, two NYPD detectives had conducted around-the-clock surveillance on my apartment and later executed a search warrant inside while I was in central booking. These were extraordinary, legally retaliatory measures taken against me because my case was political, rather than serious, or a threat to the public in any way, and as a result I had no clue how far they would keep going. Would they continue to monitor me? Would they arrest me for leaving without permission, and transport me back to New York City in handcuffs? Would the judge revoke my probation and sentence me to prison for attending a funeral?

I returned to New York and checked in with my probation officer. There was a problem, she explained calmly—a big one. My community service was outstanding and I needed to get it done. At arraignment, the prosecutor recommended three days as punishment. The judge countered with five. But then the People rescinded their offer and took the case to trial, after which they unexpectedly retreated from a dozen promises of jail time and requested fifteen days of community service. The judge bumped the number of days up to thirty. To slow down this ten-fold, game show-esque bonanza of day adding, my attorney jumped in and asked if I could use my experiences consulting in the criminal justice sector to help local nonprofit groups build capacity. Provide free services to organizations that normally cost tens of thousands of dollars on the open market.

“Your Honor—” the assistant district attorney interjected.

“Don’t worry, People,” the judge reassured him preemptively, “it’s not in the cards.”

My first probation officer spent five months trying to determine where to send me for graffiti-cleaning duty, which the judge ordered me to do instead. In May I was reassigned to a second probation officer after I appealed my first officer’s refusals to let me work and visit family. My first officer’s supervisor, when I tipped my hand and revealed where I’d once worked, reassigned me to the best officer in the department.  My second officer, who was conscientious, competent, and quite frankly, awesome, picked up where her predecessor left off. After several months of searching she learned that there were no graffiti-scrubbing outfits in all of New York City to report to.

So, after a year of wasting the probation department’s time in an effort to teach me a lesson, I was finally allowed to do what my attorney requested to begin with. I found a small startup working to prevent gun violence and we drafted a program budget, wrote new language for a website, built fundraising presentations, and raised $60,000 in grants. After I completed 210 hours almost two years to the day from when I started my probation, all that was left to do was pay off the fees, fines, and surcharges that had been levied on me at sentencing.

At sentencing, the judge had also imposed a $1,000 fine, a $200 surcharge, and a $50 DNA fee that covered the cost of swabbing my cheek. I’d once designed a demonstration project in New York City that helped probationers earn credit for the fees, fines, and surcharges they owed to the court in exchange for building a resume, going on job interviews, getting a GED, and completing job training. Because criminal justice debt leads to technical violations, warrants, and civil judgment, all of which have been shown to thwart reentry and cause serious credit problems later on, the program allowed probationers to clear these hurdles simultaneously. I’d have to toss another irony on the pile, however, because the program had been shut down in 2012.

“They’ve been entered into civil judgment,” I learned from my second probation officer, instead, concerning the unpaid monies.

“What does that mean?”

“Because of your unemployment status, they were automatically entered into default.”

This meant that debt collectors, rather than probation officers, would now be responsible for tracking me down—but I would have to worry about that another day, in the future, when I could afford to pay them and have them removed from my credit report. For now, the end of my probation was in sight, and terminating my supervision so that I could travel, spend Christmas with my family, and breathe again, was far more urgent.

“I finished my community service and I’d like to apply for termination in time to go home for Christmas,” I told the desk officer in the second to last week of November in 2014. When I was halfway through my community service, my second officer set it up so that I no longer had to report to her personally. All I had to do was show up once a month and scan my hand into a computer until my probation was over. This made reporting easier, and cut down on wait times considerably, but there was one major setback: I no longer had access to my second assigned officer, who had been a dream to work with, and who had been the only officer to let me go home twice during my probation.

“My partner and I had a baby two months ago,” I continued explaining to the desk officer, trying to stave off the inevitable “no” that was coming a while longer, “and my family hasn’t met her yet.” I didn’t mention that the desk officer sitting directly next to her had refused to let me attend my own baby’s baby shower in Massachusetts in August.

“Sorry, but that’s not an emergency,” she’d said at the time, unmoved. I also didn’t mention that I could no longer risk leaving the city without permission, as I’d done for the funeral in Boston, on account of being a new dad.

“Yeah, that’s probably not going to happen in time,” the officer sitting in front of me said, concerning my termination hearing, “those requests take several months to process.”

Years ago, in what now seems like another lifetime, I worked with high-level criminal justice stakeholders in various states. I elevated New York as a model jurisdiction during meetings with probation and parole officials, on official tours and site visits, and when chatting with officers on ride-alongs. As an early adopter of evidence-based practices, New York City’s corrections population and crime rates were concurrently in decline. Only one in four probationers failed here, compared with more than half in other jurisdictions. When I was sentenced to probation I expected to find a public safety utopia full of conscientious officers implementing evidence-based practices. Instead, over the last two-and-a-half years I have witnessed almost exclusively the opposite: a meat grinder of bureaucratic obstruction, patronization, and waiting that flies in the face of everything practitioners are advised to embrace.

One notable exception, and it does much to explain how such a high success rate can coexist with such inexplicably counterproductive practices, was a program called Employment Works. My second probation officer recommended I complete the program when I was looking for work in 2013, and rarely in all of my time in the system have I ever seen such competent, inspired people helping probationers lock down jobs, education, and training opportunities. This was exactly what probation was supposed to be doing—helping probationers find work and reintegrate into society—and yet I had to be referred to an outside agency to encounter it.

The New York Supreme Court building in Manhattan. (Bobby Constantino)

During this ordeal, I did a lot of sitting and waiting in government buildings like Manhattan Criminal Court, where I returned in December and begged the judge’s law clerk to schedule my case for a hearing. I spent a great deal of this downtime quietly observing from the gallery, contemplating the disconnect between what the system says it is doing and what it is really doing, while scrutinizing the language on the walls behind where the judges sit, and high up on the facades outside. I wondered why we seem to be unable or unwilling to keep these promises such as “In God we trust” and “Impartiality is essential to justice” to each other as Americans.

I thought a lot about this second promise two Mondays ago, while I waited for the judge to call my name after his law clerk granted my request out of sympathy, so that I could travel with my daughter. I thought about my second probation officer, one of the best I’ve encountered in the field, and about her predecessor, one of the worst. I thought about my fellow probationers upstairs on the tenth floor and outside in the rain, waiting in a line twenty deep as the judge terminated my case. But the words that struck me most during my time on probation and on trial came from George Washington. They’d been carved into the façade of the state Supreme Court building that my partner, my four-month-old daughter, and I passed below as we exited. High above, an error that would require much commitment and effort to fix remained unchanged after 87 years: “The true [sic] administration of justice is the firmest pillar of good government.”