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The Waiting Room
For many released into the harsh environment outside Chicago’s Cook County Jail, it can be impossible to find their way home.

Filed 6:00 a.m. 10.31.2018

The Cook County Jail is the largest single-site jail in the United States.

The Cook County Jail is the largest single-site jail in the United States.


Chicago's Cook County Jail is located in Little Village, an immigrant enclave known locally as "Mexico of the Midwest." It is six miles south of Chicago's soaring skyscrapers, in a part of the city where tourists rarely venture. Twenty-Sixth Street is the hub of social life in Little Village. The storefronts are vibrant with billowy quinceañera dresses and lace-trimmed baptismal gowns in glowing white. Statues of Jesus and all the saints keep an eye on passersby through plate-glass windows. The elote man sells steaming corn on the cob from a pushcart along with Jarritos sodas in red, orange and green. There is a Dollar Store with sale signs only in Spanish and fluffy blankets to lure patrons inside. Paleteros—men selling Mexican ice pops—push carts with chiming bells along the residential streets that cross 26th, blocks filled with small, single-family brick homes. In the summer, kids run after the carts and sit on the stoops of their homes to enjoy the paletas. Every year there's a fair with a Tilt-A-Whirl and a bouncy house.

A woman walks down Cermak Road in North Lawndale.

A woman walks down Cermak Road in North Lawndale.

A couple of blocks east on 26th Street, as you get closer to the jail, the landmarks and life begin to change, as if the neighborhood has been hit by a sudden disrupting force and brought to a halt. Storefronts and people slowly vanish. The only people you see in public seem to be gang members walking their turf. Here residents have erected iron fences, so it is difficult even to ring a doorbell. Move still farther east and graffiti tags cover walls, garages and trash cans. Alleys are filled with garbage and hubcaps and tires. Bar owners welcome patrons with signs that threaten that the police will be called for drugs, panhandling, prostitution or weapons.

A man sits on top of a car on Cermak Road in Little Village.

A man sits on top of a car on Cermak Road in Little Village.

Once you reach the first wall of the jail at 26th Street and California Avenue, you are still technically in Little Village, but nothing of Little Village remains. The people are missing. The color is gone. Here the scale of the vast municipal jail begins to come into view—its wall runs south as far as the eye can see, its coils of razor wire glinting in the dull light. A guard tower looms in the distance. Checkpoint Charlie of the South Side. The wall defines the contours of the largest single-site jail in America. It's been called the "Crook County Jail" and the "Hotel California," a vast jail complex the aggregate size of 72 football fields sitting heavily in the middle of a major American city. The locals quote the Eagles' lyrics "You can check out any time you like, but you can never leave" as a reminder that the punishment inside the walls seems to follow you and your family home.

A Chicago Fire Department paramedic and firefighter take a man who was shot to a waiting ambulance near the Cook County Jail in Little Village.

A Chicago Fire Department paramedic and firefighter take a man who was shot to a waiting ambulance near the Cook County Jail in Little Village.

I stood still in front of this long stretch of wall and wires on 26th Street, right across the street from the jail, where it is normal to never see another soul. Then I saw Luis. He is the attendant in the public parking lot that is the only alternative to the pricey two-hour meters, which don't even work most of the time. Luis collects money for parking and calls the tow truck on those who deserve it. And day after day, he watches the regular convoys of white sheriff's department buses moving people from police lockups around the city.

The buses, emblazoned with the sheriff's six-point star, arrive on a daily basis and disappear behind the walls. These buses do not have windows, so although Luis has watched many inmates enter the jail, he has never seen an actual human being, except for the drivers, stone-faced, transferring their cargo from the neighborhood into the system. At times the population has swelled to 10,000 inmates, landing the jail under federal supervision for overcrowding.

It's young men from Little Village and neighboring areas who are on those buses. Young Mexican immigrants like Luis and his neighbors. The vast majority of the population of Cook County Jail is black or brown. It is not until the inmates gain release—sometimes days, sometimes months after they enter on those buses—that Luis sees their faces. After being released on bond or after serving their sentences, they come to him in need. They are almost always dazed and disoriented. Sometimes he'll call their parents for them. Other times he gives them a few bucks for the C.T.A., because the one bus pass from the sheriff is never enough to make it home.

A Cook County sheriff's bus leaving the Cook County Jail.

A Cook County sheriff's bus leaving the Cook County Jail.

As Luis and I chatted, we hid under the hatchback of his car as a sudden rainstorm poured down. Luis studied the front of the jail as if looking for signs of life. "The first day that I was here, it was actually quite depressing," he said. "'Cause I see a lot of buses, and I know they're filled with kids. When they release these kids, sometimes they don't have anything to get home. They come in with money, but they take it from them and write them a check when they're released. They are disoriented, they even forget how to take the bus to go home . . . I see the families when they come out, and they are crying. I see a lot of emotions."

Spend enough time here and you begin to understand that a jail like this in a city like Chicago was never designed to spare those whose only offense is living next door.

People wait at the Cook County Jail for loved ones to be released.

People wait at the Cook County Jail for loved ones to be released.

Just inside the wall, Florna Zaya's wait is just beginning. Waiting to post bond, waiting to be reunited with her son, waiting. In the waiting room, families squint in confusion at a digital electronic board that tracks departing inmates like trains at an Amtrak station. They look for names, discharge status and the estimated time of release, which is always off by hours.

Waiting can be a weapon. Or at the least, waiting is a way for the state to tell you that your time, and thus your life, is neither yours to control nor worth very much. A century ago, a debtor's prison stood on this site. In the early 1920s, when Chicago's city fathers were looking for a place to punish people, close enough for guards and lawyers to reach but at a proper distance from polite society, 26th and California was thought an ideal spot. Admonitions from a minority of city leaders worried about making a ghetto of the old Bridewell neighborhood were ignored: the area happened to be located in the county president's ward, and those were the days when politicians saw having the biggest municipal jail in the country in their backyard as something of a plum.

And so, on the 30th day of March 1929, a type of punishment then described as "compulsory idleness" commenced here and has not let up since. This idleness that was imposed on inmates was even then recognized as a killer of the mind and spirit—the sheer torture of inactivity. And it wasn't just the idleness, it was the uncertainty. An inmate's days were filled with waiting—winding down a sentence of indeterminate length, without benefit of knowing when it would end.

People wait in line to make bond payments at Cook County Jail.

People wait in line to make bond payments at Cook County Jail.

Uncertainty can be maddening. By 10 a.m., Florna Zaya's wait for her son is a couple of hours old. She found herself pacing the hallways, searching for anyone who might be able to help her, looking for a bathroom with toilet paper. Her day would take her from the courthouse, to the bond court, back to this room where all there is to do is wait. When the time comes, detainees will be released in groups of twos and fours. The correctional officer at the security desk will yell, "We got people coming out . . . Four up!" With that, the room, full and quiet before then, will be stirred into motion, everyone suddenly on their feet, pressing together in front of a viewing window to see if one of those four people gaining release belongs to them. Probability being what it is, most of them will turn and silently shuffle back to their seats. The freed detainees will carry their possessions in plastic garbage bags, knotted and sealed. Any money they had when they were arrested will have been converted to a Cook County–issued check that is unusable for the "release and run," as it is known. Some will have no idea which way to turn as they leave the jail, and no one will know what to do with a check. There is a currency exchange on Kedzie Avenue and 26th, but that is a 13-minute walk, past the desolate zone next to the 26th Street wall of the jail, where it's not unusual to get jumped by gangs. The Popeyes at California Avenue used to be a good place to get your check cashed, and it was such a reliable sanctuary in the neighborhood that the sheriff's department would send the newly released detainees there, making it a regular stop in the out-processing.

The Popeyes in Little Village, Chicago, was once a refuge for people just released from the Cook County Jail.

The Popeyes in Little Village, Chicago, was once a refuge for people just released from the Cook County Jail.

For generations, that Popeyes was a nighttime safe house for those released from jail but not yet free from the dangers around it. Late into the night, released detainees could get a cup of coffee, make a phone call or get their money. For those who were gang members, Popeyes was a neutral zone where rivalries were suspended because everyone could agree on a common enemy—that jail and those correctional officers who released them with no money, no coat and a bus pass that wouldn't get them all the way home. But that had changed a few months back when the place was shot up in broad daylight. Tired of it being a gang target, the manager had grown hostile to detainees. And so now there is nowhere to go.

Patrons wait in line at Popeye’s restaurant near the Cook County Jail in the Little Village neighborhood.

Patrons wait in line at Popeye’s restaurant near the Cook County Jail in the Little Village neighborhood.

Back in the waiting room, small lockboxes imprison all the visitors' cell phones; phones are prohibited in the waiting room to prevent anyone from taking pictures. And so those waiting are as cut off from the outside world as their incarcerated family members. And the waiting families are solemn in their compulsory idleness. The correctional officers, on the other hand, joke around and laugh loud and long. The contrast is jarring.

Correctional Sgt. Michael J. Mazurek works the desk and describes the process of bonding out of jail and getting home. Even after paying bond, inmates have to be checked for outstanding warrants before they can be released. Once a person's bond is paid, it can be as "quick as two hours," which he notes is rare. "I've seen seven hours . . . I've seen a person turned back because they had unpaid parking tickets in Milwaukee."

If they're cleared, he says, "they get a bus pass and two transfers and a phone call in the bullpen about a half an hour before they walk out."

What do you do if they don't have anyone to call?

"I've never heard of anyone saying, 'I can't reach anybody. I'm not leaving.'"

Men sleep on bunk beds in Division 4 of the Cook County Jail.

Men sleep on bunk beds in Division 4 of the Cook County Jail.

Mazurek is a voluble man and doesn't get shy around reporters. He talks about the changes in the jail, talks about the declining population of the jail under the "reform" sheriff, Tom Dart, and goes back in time to when he was just getting started—a time when the most violent offenders were housed in Division 1.

Division 1 was the oldest part of the jail and had held some of the most notorious mobsters and killers—Al Capone, Richard Speck and John Wayne Gacy, to name just a few. In an old Chicago Tribune article, Lt. Leroy Moore, a top Division 1 corrections officer, described his work: "You ever had a dream where there is a huge ball of fire and you're entering hell? Well, this is it. This is worse than hell." Mazurek saw that hell firsthand. Now that the division is closed, and Mazurek has survived, his eyes get wide as he tells stories. Sometimes, he says, for the safety of everyone involved, the most violent inmates were not allowed to shower. Instead, they were shackled, stripped naked and washed in their cells. They were chained hand and foot, with chains running between, and the sheriff controlled the inmate with a leash. If there was any sudden movement, the officers gave them the "lawn mower," yanking upward on the leash to make the prisoner fall hard to the concrete floor in submission. Mazurek gets more excited as he talks, swiping his fisted hand upward like he is cranking the chain, like he is right back there for a moment.

A man at the Cook County Jail's Division 4 consults with Robert Harmening, right, population manager for the Cook County Sheriff's Department.

A man at the Cook County Jail's Division 4 consults with Robert Harmening, right, population manager for the Cook County Sheriff's Department.

As Mazurek reminisces, Florna wears a stricken look on her face. And the room, already quiet, becomes funereal. Does that still go on here? Where's my son? Where is he?! No one tells Florna how this all works; no one tells her that the bond court doesn't even open until 1 p.m., and so she loiters nervously.

Perhaps it is a mistake that the police do not tell her the time or exact location where she would be able to find her son; perhaps it is not. Sometimes the staff are overwhelmed. Sometimes they are genuinely cruel. When I worked as a law clerk in the Cook County prosecutor's office, the deputy sheriff assigned to our courtroom would brag about how she would torment families of defendants. When families called the courtroom and tried to locate their loved ones and their cases, she answered the phone with a jovial, "County morgue." She would then pause as though she were checking on the defendant's name and say, "Oh, they're dead," and then hang up the phone.

Florna's son is alive. But she is panicked about what condition he might be in. On those windowless buses, she's heard how men charged with violent offenses posture for power, taunting the weak, creating a terror of being raped that might as well be the assault itself.

As Florna wanders the hallway outside an empty bond court, a deputy sheriff takes pity on her. "Ma'am, I have been on this job for 18 years. I don't care what the police told you. Your son is going to be here all day."


“We got guys coming!" the correctional officer shouts. Within moments, men run, hands in their pockets, onto the cement walkway outside Division 5 of the Cook County Jail. At first they seem to be running from the jail like it's chasing them, but once they are on California Avenue, the race changes, and they now look like they are being hunted by the surrounding area. Awaiting these men is the brutal Chicago cold, the prospect of being jumped by the Latin gang that owns the area and the likelihood that to get home, you will have to walk 15 miles alone as night comes on.

Darius Roberson bonded out of Cook County Jail in Chicago the night before Thanksgiving.

Darius Roberson bonded out of Cook County Jail in Chicago the night before Thanksgiving.

Darius Roberson emerges from this pack of men, dazed and squinting. He is easy to spot because he is standing still. He is a large man, dark skinned and mumbling to himself in frustration. While the other men run, Darius pauses and looks around as though he is trying to find visual landmarks to tell him where he is. At one point, he even walks back into the jail for help, fighting his way upstream while everyone else who knows better is swimming the other way. I push upstream as well and hear Darius mumble, "There's a total lack of information."

The temperature is below freezing, but the men running from the jail are dressed for a different season, frozen in time, wearing the same clothes they were arrested in during the summer. They wear cotton jackets and sweatshirts; some men wear T-shirts. "Hey!" I yell. "Where are your coats? Aren't they supposed to give you a jacket?"

"They told us the jackets got bedbugs," a voice echoes as it passes. Another man stops. "Are you an attorney?" he asks.

"No," I say. "Did they give you a coat?"

"They told us the poor box was infested with bedbugs. I wasn't going to risk it." The correctional officers have peddled the bedbug line for so long it's become lore. It's hard to say if it's more degrading or inaccurate. Either way, it sounds like a cruel joke—why bother having a box of coats if you can't at least make sure they're not contaminated? Once the man realizes that I can't help him with his case or get him a ride home, he starts running again but yells back at me. "You should check out the homeless man. They held him back for a little bit because he got nowhere to go . . . I don't know what's going to happen to him. He lives under a bridge . . . They should help him or something!"

"There's some people who need psychiatric treatment as well," another man says. The men run as they give these warnings and tips, leaving me to hustle with them just to hear what they have to say.

Darius comes up to me and confesses, "I took one of the bedbug coats. I figured I had no choice."

Being released on bond from the Cook County Jail is a sort of "Hunger Games" footrace into a landscape of vacant lots, smokestacks and abandoned buildings. Shoes hang by laces over electrical wires. Gang tags cover concrete walls. Side alleys are festooned with yellow "rat control" signs stapled to wooden poles. Well-worn plastic sheeting hangs on fences to block the imposing view of the Cook County Jail from those living on the other side of the rusted chain-link.

The majority of those incarcerated are young African American or Latino males under the age of 34, from Chicago's South Side and West Side—a perversely convenient arrangement, as the jail is closest to its target population. Darius fits this profile, but it is clear that he does not know the rules of engagement. He doesn't understand that he had better be running, and it is clear that he is unaware of the dangers that face him outside the walls of the jail. And anyway, he doesn't have that many choices.

The Cook County Jail is a vast complex the size of 72 football fields.

The Cook County Jail is a vast complex the size of 72 football fields.

If you stand in front of the Division 5 exit and face south, factories, smokestacks and sidewalks route you away from civilization and toward absolute darkness. Some men unfamiliar with the area try their luck in that direction. If you look to the left, into the distance on 26th and California, there is the Popeyes, the only sign of life save for Luis's parking lot in the alley right next to it.

Once you get to that corner—26th and California—you see the freeway entrance to your right and a long, desolate stretch of dark terrain that traces the walls of the jail. About three city blocks west on 26th Street is a Walgreens, the first store and sign of civilization. The cashier there says that men often arrive at the store with blood on their faces, asking for modest help: a paper towel, a phone to call home, momentary safety.

If you're lucky enough to have someone waiting for you, you can go straight out of the jail to California Avenue, where cars idle in a line, waiting for those who have just bonded out. Children play on iPads that shine through the dark windows of worn minivans. Others sleep with their hoods covering their faces. Exhaust fumes keep the cold air thick. The tired prisoners pile in and exchange quick hugs with their loved ones, and cars pull away and head to I-55 south.

Darius doesn't know what waits to the right or the left. No one is waiting for him. As the rest of the men run past, Darius asks quietly, Where am I? What day is it?

Darius was arrested two days ago, but in his disorientation, he thought it was three days. He had just gotten a new roommate, and there was an argument. The argument had escalated and become violent, and Darius had the defensive wounds on his arms to prove it. He had blocked his head and face while the roommate was in a rage. It was clear that Darius needed somebody to know that he was innocent, and showing his wounds was helping him prove his case.

When the police had arrived at Darius's home, he was indignant. He was appalled at being beaten by someone he lived with and furious that the police were at his door. His defensive wounds didn't matter to the cops. His words didn't matter. None of it mattered. His outrage was enough to get him arrested; his attacker was left to go about his business.

Darius's phone was taken at the police station. He spent the days trying in vain to remember even one number from that phone, just one person he could call to post his bond. Then he wrestled with fear: missing work and failing to call in sick could get him fired. But even if he could call, how could he tell his boss where he was?

Shame and desperation are a poisonous mix. You need help to get out of jail, but the shame of being there prevents you from asking for it. The trauma from the beating at the hands of his roommate, the disorientation—first of the lockup, then the windowless bus—and now the constant chaos and the relentless air of violence at the county jail left him with little memory or capacity to think. To the world, Darius had just vanished.

Inside the wall, days turned into nights with no markers of time. Was it hours passing, or were those days?

"You should know this!" the correctional officers yell at the detainees, assuming they are all familiar with the customs of the jail. But Darius had never been in jail before, and he was scared. The more you protest your innocence, the more the officers hassle you; the more questions you ask about when you get to leave, the longer you are going to be there. Darius got lucky, though, managing to align himself with a kindly inmate who taught him the rules of engagement—the threats from the gangs, who the power brokers were on the inside and how to recognize them. This man also identified the types of men that would likely be victimized. That way, Darius says, he could learn to avoid their mannerisms. The word rape is used often. When I ask Darius about whether he saw any attacks, he says, "I think they got some people . . . just not me. I don't know." Behind his eyes, Darius is elsewhere. He is standing next to me outside the jail, but his thoughts are locked inside.

As he stands there at the Division 5 exit of the jail, Darius's disorientation is clear. He can't turn right because that's Latin gang territory. Left is Popeyes, which isn't safe anymore. Where on earth can he turn?

The streets of Chicago around the Cook County Jail and the Little Village neighborhood.


There is a new sheriff in town. His name is Tom Dart, and like the new state's attorney, Kim Foxx, Dart thinks of himself as a reformer. He famously wears street clothes on the job instead of a uniform and has said that half of the inmates at the Cook County Jail shouldn't even be there. He has evinced sympathy for the third of the inmates at the jail who are mentally ill (which makes the Cook County Jail the biggest, and worst, mental-health facility in the country). Further laying claim to the reform mantle, one of Dart's spokespeople told me that everything the sheriff's office does "is done in a just way despite being a component in an unjust system."

Law enforcement officers adore this kind of talk. When he talks about the "unjust system," he's talking about them. I found several in my time at the jail who were quite open with their feelings about the sheriff. "Oh, you mean Sheriff Goofy? That fucking guy?" one of his deputies said. The rank and file call him Sheriff Goofy for implementing programs that teach inmates how to cook, play chess, create art and manage anger and trauma through yoga and meditation. They see Dart's sympathy for inmates as mostly a play for good press and figure that Dart is campaigning for mayor on the public dime. But the officers also see the reform sheriff as an affront to their prerogatives and to their safety. This is their goddamn jail.

Several officers I talked to were just biding their time until retirement.

In the years before Dart took over the sheriff's office, the average length of stay at the Cook County Jail increased by 6.2 days, from 47.9 to 54.1 days in jail. But since Dart went on "60 Minutes" last year and told the world that half the inmates in his jail shouldn't even be there, he has worked to lower that number—by reforming bail so that the county doesn't hold people just because they can't afford to bond out (Dart was court ordered to do so) and establishing a "rocket docket" for nonviolent offenders to process their cases in 30 days or less. And he has done something a little more controversial—he has increased home electronic monitoring (EM) to transfer inmates home, essentially warehousing them in the neighborhoods. This often happens in the dead of night.

Shortly before midnight, Andy and nine other inmates sit in a Cook County sheriff's van near one of the checkpoints around the jail. They have been waiting there for two hours. Their driver and guards, two Cook County sheriff's officers, smoke cigars in the distance. At first, Andy and the other defendants were pissed off, confused, and used the first hour in the van to complain about the absurdity of being driven feet from the Cook County Jail only to sit at a sheriff's station while the good ol' boys savored their smokes. With the second hour in the van came the silence that accompanies submission.

The two officers were supposed to be returning Andy and the other released inmates to their homes, setting up each man with an ankle bracelet, to shift their incarceration from the jail to their homes. But by the third hour, Andy realizes that these officers have decided to let the next shift deal with the vanload of anxious prisoners. As the men watch from the windows of the van, the officers talk and joke and smoke as though they were off duty.

Andy thought he was one of the lucky ones; and an inmate allowed to go home on EM is lucky indeed. After hours in the bullpens and being shuffled from cage to cage, he was sorted into a select group of low-risk prisoners who would be tethered to their houses. He would finally see his girlfriend, who was preparing a meal, and he wouldn't have to wear a jail jumper. Soon, after 48 hours of transport, intake and incarceration in Cook County Jail, there would be a homecoming.

All of this, he says, was a result of a political protest gone wrong. He doesn't really want to talk about it in any detail, but he was arrested and accused of destroying public property, and that was enough to commence punishment before a conviction. The judge seemed to want to teach Andy a lesson. He had no felony record, but his bond was set high. He would get a $100,000 D-bond, which meant that he would have to pay 10 percent of that to earn his true freedom from EM. But because he worked "irregular" hours, the sheriff's department would not approve him to leave his house for his job, which paradoxically makes it impossible to come up with $10,000. But he'll be out, and sort of free.

In anticipation of his release, earlier in the evening Andy had received meticulous instructions from the officers about how his journey home from the jail would go down. If the prisoners didn't follow the instructions to the letter, they would be sent back to the jail, with dim future prospects of release. Andy was told that he and the other EM prisoners would leave in a secured van around 10 p.m. from 26th and California Avenue. Based on that departure time, estimates were that they would arrive at Andy's home in Humboldt Park, a straight 5-mile shot from the jail on Kedzie Avenue, around midnight. If the house wasn't awake and no one came to the door to receive Andy, he'd be returned to jail—no banging on the door, no waiting for somebody to climb out of bed and make it to the door. If no one answered on the first knock, they'd be gone. If someone opened the door to them, the deputies would commence the installation of the EM machine. The ankle bracelet would be locked in place and would transmit his precise whereabouts to the jail at all times. The jail would know if he crossed the threshold of his house, even to throw out the garbage.

This idea of returning to jail is too much for Andy to bear. He already spent days waiting in the local police lockup with its bright fluorescent lights and relentlessly cold cells. He slept sporadically, half in a dream, sometimes nauseated but consistently hungry. He ate the bread from the stale bologna sandwiches, but as a vegetarian, he could not bring himself to choke down the rubbery meat. Andy had been transferred by paddy wagon to the Cook County Jail, shackled to other inmates and to the seats of the vehicle.

Because the risks of being sent back to jail are so high, Andy memorized the sheriff's protocol in his head. He made contact with his roommates so that they knew just how seriously the rules had to be taken and just how high the stakes were should they not get it right. In fact, they were up and waiting all night. To pass the time, they readied the apartment for a visit from law enforcement. Political posters associated with Andy's arrest were taken down. The place was cleaned up for inspection. They scanned for anything that could jeopardize Andy's return.

With military precision, the van left the jail at 10 p.m. and promptly stopped a stone's throw away so that the officers could light up their Montecristos, with military precision, as the prisoners moldered away in the van, packed knee to knee. Rules and protocols were only for prisoners, it would seem.

Cook County Sheriff's officers are omnipresent in the community around the jail.  Here a man is stopped by five officers and is accused of breaking into cars.

Cook County Sheriff's officers are omnipresent in the community around the jail. Here a man is stopped by five officers and is accused of breaking into cars.

Finally, the next shift begins. Two more sheriff's deputies climb into the van, and they are off. They make their first stop at a local gas station, and from there the officers make their way into the attached Dunkin' Donuts, order coffee, find their way to a table and sit. The mood in the van is of sheer disbelief. You've gotta be fucking kidding me. It is about 1 a.m. before the van begins moving again, and when it does, the officer behind the wheel drives through the West Side at 20 miles per hour—as slow as you can go in the right lane without stopping traffic. It is a speed that must have been practiced—fast enough to make progress to the first house but slow enough so that driving and dropping off 10 prisoners will take the entire shift.

Nothing is logical about the sheriffs' route. They drive in circles, too far out of the way to the west and then too far out of the way to the south. Between the sleeplessness and the endless nonsense route and the night's normal surreality, the van takes on the air of a carnival ride, and you just can't get off. There is no warning whether you are next—only guessing, praying, sleeping and looking out the window. The officers disappear into each house with their EM system and the necessary tools to get it working. Exhausted women answer the doors, often holding a sleeping child. Sometimes EM systems are easy to install. Other times they don't work. At the fourth or fifth house, the EM monitor will not install correctly, and Andy overhears the officers mention the need to go back to the jail. By then it is 3:30 in the morning and a sense of panic sweeps through the van. By some act of God, after an hour at the problem house, the officers successfully install the monitoring system and are on their way again.

An abandoned building in North Lawndale, not far from the Cook County Jail.

An abandoned building in North Lawndale, not far from the Cook County Jail.

Another night, another vanload of prisoners extending the jail's reach deeper into the neighborhoods. Andy is the seventh person to be dropped off—in Humboldt Park by way of North Lawndale, Garfield Park, Homan Square and all the other mass-incarcerated parts of the city—joining the 2,000 other Chicagoans confined to their homes by electronic monitoring at any given time. (By contrast, the jail population as of this writing is about 6,000.) He crosses the threshold of his home at 5 a.m., his 5-mile journey having taken seven hours. His friends have been waiting since midnight, fighting sleep.

Tom Strening, the board president and chaplain for Courtside Ministries, right, leading a prayer outside the Cook County Criminal Court in 2016.

Tom Strening, the board president and chaplain for Courtside Ministries, right, leading a prayer outside the Cook County Criminal Court in 2016.

Next Day

On California Avenue, near the entrance to Chicago's criminal courthouse, Tom Strening, the board president and chaplain for Courtside Ministries, sets up his prayer table for the day. The table is covered with his signature blue tablecloth and his logo spells "Courtside" with a crucifix for the t. Alongside the free Bibles are pamphlets for homeless shelters, addiction centers, job-training resources, counseling services and numbers for cheap or free legal services so even the poorest defendants can get a lawyer. Sometimes Tom's volunteers give a dollar or two for bus fare to help those just getting out. Sometimes they give them a dollar to pay the food-truck man, whose side hustle is holding the backpacks that are barred from the courthouse. Strening and his volunteers are also good for the use of a cell phone to call friends or family to get a ride. The Courtside Ministries also offers prayers to all comers, and Strening says that those services in particular are always in high demand around the jail and the court.

This morning, as Strening arrived to set up his table, he found someone in his normal space: a man who had just spent 47 days in jail for stealing a winter hat.

Correctional officers released him at 4 a.m. so that he might avoid the gangs—he might have been free, but he had nowhere to go and no way to get there. And so, exhausted, the man slept on the sidewalk next to a garbage can, near where the prayer table would take up its post. Tom greets him good morning. "Would you like some prayer before you go?" And so they pray.

Strening is never one to judge. He has prayed over a steady flow of people facing their worst days, people looking for answers, strength and peace. People released from the jail, disoriented, exhausted and trying to make it home. People who lost sons and daughters to violence. A man who walked out of jail sober but who isn't anymore. A woman scared to testify because she is terrified of gang retaliation. And then there are the people who just need an embrace. A few days ago he prayed for a man and then wrapped him in his arms, which was enough to make him start bawling right on the courthouse steps. Moments of true grace in a bleak spot, moments that materialize and then vanish with little evidence they ever were there, moments made by people who go toward desperation rather than turn away.

Moments like the alternative poor box that another minister sets up on these streets from time to time. He drives from Rockford with boxes of warm clothes, with no bedbugs, guaranteed.

Residents of Little Village pick through clothes donated by a church.

Residents of Little Village pick through clothes donated by a church.

Moments like when the Chicago summer comes, and with it the carnival, and the vibrant community west of the jail migrates to the wide and empty spaces right outside the wall for just a few days, and when the Tilt-A-Whirl spins, for just a moment you can see over the wall and they can see you. Children write messages of hope on kites and fly them above the wall—in Spanish, one kite says, Let me fly. Let me live. Let me dream. Let me feel. Another kite, lodged in the tree, carried the message, "You are not forgotten."

Moments like when Florna Zaya rushes to the window to see her son born back into freedom, like it's the window of a maternity ward. She embraces him there in the concrete corridor just outside the Division 5 waiting room, with her cheek pressed against his shoulder, brushing his hair and face as if to check whether there was any damage. She takes a moment to wave to me and points to her son with pride.

Moments like when Darius Roberson, who is traumatized and struggling to recover from his time in the Cook County Jail, calls to check on me.

Moments like this:

Judging is not part of his ministry, but that morning at 4 a.m., when Strening found the man sleeping on the sidewalk, he decided that the best thing he could do is try to impart some wisdom born of his faith: Ask God for something before you steal it, he told the man. God will provide, even a hat.

The man looked at Tom. "You're right!" he said. And then he grabbed a fitted winter hat from his pocket. "I was sleeping over there by that garbage, and this was sitting right in front of the garbage can when I woke up. It fits me perfectly."

Forty-seven days in, and what he needed was waiting right there for him when he got out.

About the Author

Nicole Gonzalez Van Cleve is an award-winning author and an Associate Professor at The University of Delaware in the Department of Sociology and Criminal Justice. Her book, "Crook County: Racism and Injustice in America's Largest Criminal Court," is an NAACP Image Award Finalist and a two-time Prose Award Winner for Excellence in Law and Legal Studies and for Excellence in Social Sciences. Her legal commentary has been featured on NBC News, NPR, CNN and MSNBC's The Rachel Maddow Show.


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