• Precarious Liminality: How Parole Keeps Ex-Prisoners Stranded Between Two Worlds

    Ben Austen Follows One Man's Path From Incarceration to Supervised Freedom

    September 26, 1983

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    Mr. Henderson is a 30-year-old offender who is serving his tenth year of incarceration on the instant offense. The psychological summary states that given “the nature of offense and his past record,” that a degree of caution is still warranted. He still has not secured marketable skills to enhance free community integration.

    Each time the members of the Illinois Prisoner Review Board voted to reject Michael Henderson’s parole, they sent him a letter explaining the rationale behind the decision. Parole candidates didn’t attend their hearings in Springfield. The rationale letters were how they found out why they were denied, and what, if anything, they could work on for next time.

    February 26, 1986

    The record reflects that you are serving 100 to 200 years for the murder of Ricky Schaeffer, which occurred during an armed robbery in East St. Louis in 1973.

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    After a careful review of all the material presented, the Board feels due to the violent nature of the offense and your complete disregard for human life, to parole you at this time would deprecate the seriousness of the offense.

    A prison term of a hundred or two hundred years made no biological sense, like something out of the Old Testament or science fiction. But Michael’s sentence was indeterminate.

    Meaning, it was left up to a parole board to determine when the punishment would end.

    And, in theory, it was also up to Michael, since he could demonstrate through his behavior and understanding of his crime that he no longer posed a threat to society. That he was remorseful, reformed, and deserving again of freedom.

    December 11, 1992

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    In 1974 Mr. Henderson was sentenced to a term of 100–200 years for the murder of an innocent man whom he shot without provocation during an armed robbery. Mr. Henderson then robbed the body and vandalized the victim’s car.

    The rationales contained errors at times. (Michael’s crime occurred in 1971, when he was eighteen; Michael shot Schaeffer—accidentally, he still insisted—but he didn’t rob the other boy’s body or vandalize his car.) The letters varied from addressing the parole candidate directly to speaking about them in an administrative third-person. At the actual hearings, board members may have disagreed, even debated vigorously, but the rationales were written in a collective voice. The board’s reasoning was spoken as one.

    April 18, 1997

    After deliberation, the Board denies parole due to the brutal and senseless killing of an innocent victim and the inmate’s inconsistent disciplinary reports, many of which are for substance abuse, which the inmate has not been successful at addressing. 

    As official documents, the rationales also captured the passage of time. All that changed over decades, and how much remained the same.

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    April 10, 2003

    Although, the Board recognized his positive institutional adjustment, it is felt that parole at this time would deprecate the serious nature of the offense and promote disrespect for the law.

    What was the punishment supposed to accomplish? And when was it enough?

    May 11, 2006

    Mr. Henderson is 53 years old and has served almost 32 years…… Mr. Henderson stated that he did not intend to shoot the victim and was just trying to scare him and the weapon discharged after the car moved.

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    May 27, 2010

    Mr. Henderson expressed remorse and is capable of complying with the conditions of parole.

    February 23, 2017

    Inmate Michael Jerome Henderson C10609 is a 63-year-old African American male, who was born on March 16, 1953 to Ida Lee Henderson and David Henderson. Inmate Henderson’s mother died in 2010 and he claims to have never met his father.

    Inmate Henderson has four children 13 grandchildren and 4 great-grandchildren.

    In regards to Inmate Henderson’s health he runs 10 miles per day and credits his love for running as a mechanism to cope and work through stress.

    Inmate Henderson has admitted to shooting Richard Schaeffer and says that his mistake haunts his own life, the lives of the victim’s family and the lives of his own family. Inmate Henderson understands that nothing can remove the pain from the Schaeffer family

    After a complete discussion by the Board and a review of all the facts, the Board voted to deny parole at this time. The Board felt that to grant parole would show complete disrespect for the law.


    On the morning of December 13, 2018, someone assaulted a guard, and the entire prison was on lockdown. Two thousand men confined to their cells. A few of the guys on Michael’s wing asked him about his parole hearing taking place right then in Springfield. But Michael deflected their questions. It wasn’t that Michael didn’t believe in his chances. He did. He was incapable of thinking otherwise. As congenitally self-assured at sixty-five as he had been at half that age, Michael had faith that the board members reviewing his case were bound to see him, at some point, the way he saw himself. Yet he’d felt the same inevitability before, for decades even. So he hadn’t made any farewell plans this time.

    What was the punishment supposed to accomplish? And when was it enough?

    In 2016, Marjorie Moss, a lawyer and social work supervisor at a legal clinic at Northwestern’s law school, agreed to represent Michael pro bono at his next hearing. She drove 250 miles south to his prison, and they spoke for hours. Moss was trying to get two other people out on parole as well, but meeting Michael energized her.

    “Oh my God, this guy has to come out,” she said upon her return to Chicago. Michael’s crime—a Black-on-white homicide—was committed when he was a teenager. Richard Nixon had been president. Gas had cost thirty-six cents a gallon. Nearly fifty years later, Michael was an old man. The recidivism rate for people his age, especially those whose crime was murder, was miniscule. Moss sent Michael a book on training for marathons. She said they could run the Chicago Marathon together, if and when he was set free.

    Later that morning, a female correctional officer came over and said Michael had an attorney call. She escorted him to the phones.

    “Michael,” a voice, barely audible, said on the line. It was Marjorie Moss. “Michael, Michael, Michael,” his lawyer repeated six times, her voice trailing off into silence.

    “What?” he asked. But Moss didn’t answer. Michael thought he heard crying. He started to hyperventilate. He couldn’t breathe. Moss finally managed a reedy reply.

    “I think Christmas came early for you.”

    She said the board members debated for a long time. But they decided finally that Michael, after forty-six years, could go free.

    December 13, 2018

    The basis for the Board’s decision at this time is explained as follows: Reviewing all factors available at this time, it is the Board’s conclusion that the subject is a good risk for Parole.

    The vote, in fact, had been unanimous, fourteen to zero. Moss said one of Richard Schaeffer’s brothers, who was now an old man himself, came up to her after the decision and said he understood that enough time had passed. He said his family was going to be okay.

    “I’m dreaming,” Michael said. “This is not true.”

    It was true, Moss assured him. He was leaving prison. He was being paroled.


    Michael, now a parolee, sat on the train to Chicago, unsupervised yet feeling watched. It must have been obvious to all, he thought, that he was straight out the penitentiary. He might as well have had a sandwich board hanging from his neck that announced “CONVICT.” It was December 2018 and freezing out, yet he didn’t have a coat. He didn’t have a suitcase either. All his belongings were stuffed into two stretched-thin garbage bags piled at his feet. His leaving was surreal. From the moment he spoke to his lawyer, Michael felt like a different person. He’d been reborn. And now, for the first time in a half century, he was on his own.

    On the ride to Chicago’s Union Station, Michael turned to a conductor to ask permission to leave his seat. He had to use the bathroom. He caught himself and chuckled nervously. It was the penitentiary mindset. Freedom would take some getting used to. Michael studied the passengers around him. It was his first time seeing it—a crowd of people, all of them bowing their heads into cell phones, as if in group prayer. No one was interested in him. A woman bumped into Michael and didn’t say excuse me. He choked back the urge to yell, “Hey, I’m here! I just got out! Hello!”

    The train pulled into Union Station shortly before midnight. Michael edged his way onto the platform, lugging his trash bags as he scanned the crowd. There was Marjorie Moss, standing beside her husband. Michael and his lawyer embraced. She snapped a photo of him posing in front of the station’s giant Christmas tree. Michael hoisted the two garbage bags over his shoulder, like Santa Claus. One of the plastic bags opened like a chute. Forty pounds of books, photos and documents splashed onto the ground.

    Michael’s new residence, at least for the next several months, was a group home on Chicago’s West Side, a transitional halfway house for people reentering society after prison. It was called St. Leonard’s House, and Moss planned to drop Michael there. She asked if there was anything he wanted to see first. Was there some food he’d been dreaming of? What popped into his head now was a banana. The potassium. When he ran at the prison, he thought constantly about the lack of fresh fruit. They dropped into a newsstand inside Union Station, and Michael picked out four bananas. The first one was gone in three quick bites. Out on the street, Michael paused and took in the world around him. The orderliness of the parked cars one after another as if on a chain. The long shadows of the street lamps. Everything sparkled with strangeness. That would soon fade with familiarity. But in that instant, Michael imagined he would spend the rest of his days in awe of these everyday delights. The orange winking of a “DON’T WALK” sign. The wide boulevard gullied by a dark SUV, which seemed as big and fast as a torpedo. Michael was now a part of this world. “They don’t know me from the man in the moon! And I don’t know them,” he sang. “But I love them!”

    They arrived at the halfway house well past midnight. Michael saw a couple of people in front of the two-story brick building with flashlights. “Welcome home, brother,” someone shouted. They were there to greet him. Two men took turns clasping hands with Michael, pulling him in for a hug. Many of the employees at St. Leonard’s were former residents, meaning they’d been incarcerated themselves. Michael looked for familiar a face, anyone he might have done time with. At that hour, he didn’t recognize a soul. So he did what he always did—he stayed quiet and observed. Know everyone before they know you.

    Michael followed a man inside. Michael was handed an assortment of toiletries. He’d get new clothes in the morning. He was led up narrow stairs, each creaky step like hitting the keys on a pipe organ. At the end of a hallway, he was shown a room with three single beds. In the dark, Michael could make out the outlines of sleeping men in two of them. Michael shuffled to the third cot and stowed his bags. He returned to the hallway and washed up in the communal bathroom. When he lay down in his corner of the room, he reviewed his day, as he’d done in a cell every night for decades. There was a lot to cover.


    Since 1982, Michael had come up for parole consideration thirty-six times. In 2018, he made parole. But “parole” the noun and verb was also a state of being, a precarious liminality between two worlds. Michael was now on parole, which meant he was out of prison but still supervised. He had to check in regularly with a parole officer and abide by the conditions of his release. Parole in this sense refers not just to people who were technically freed by a parole board; it also describes everyone released from prison who, as a stipulation of their sentence, had to remain under the custody of the Department of Corrections for a period of time while out in the world. On parole is also known as mandatory supervised release, MSR, or community supervision.

    “Parole” the noun and verb was also a state of being, a precarious liminality between two worlds.

    Being out on parole, like its cousin, probation, operates as an alternative to physical confinement. Instead of staying behind bars, a person is monitored and controlled in the community. It is significantly cheaper to supervise someone outside of prison or jail than to lock them up, about a tenth of the cost. While parole is tacked on after a prison term, probation is a form of community supervision given at sentencing as an alternative to incarceration. Someone on parole, or on probation, wasn’t yet returned to full citizenship.

    Michael met his parole officer and was fitted with an electronic ankle bracelet that relayed his whereabouts. He had to wear it for four months. From seven in the morning to seven in the evening, he was free to leave St. Leonard’s; he could visit a grocery store or go on a jog. But every night he needed to be back at the halfway house, near the monitor’s base in his room. Otherwise an alert would be triggered and he’d be in violation of his parole. Michael assured Moss that he wouldn’t mess up. He would conform to the conditions of his release. He would stay out of trouble. “I’m not coming back to prison,” he’d tell people he encountered. “I intend to be successful in whatever I get involved in.”

    But on parole, Michael faced an array of potential pitfalls. If he missed a seven o’clock curfew or didn’t show up for an appointment with his parole officer, that was a parole violation; he would have a “revocation” hearing and might have to serve out the entirety of his remaining term, which meant a release date around 2070, when he would be 114. If he left the state, he was also in breach of his parole restrictions and could be returned to prison. If he tampered with the electronic monitor attached to his ankle, he was similarly in violation. If Michael failed to report that he’d moved, or failed to find housing or employment, he could be violated as well. If he drank alcohol or smoked marijuana or tested positive for any controlled substance or entered a bar, he could go back to prison.

    The list went on. According to the American Bar Association, there were 45,000 federal and state laws regulating what a person couldn’t do once they left prison on supervised release. As a parolee reentering free society, Michael would be sent back to prison if he committed another crime, of course, even a misdemeanor. But the same could happen if he was arrested and never charged with a crime, even if the arrest was for disorderly conduct or loitering or resisting arrest, the sort of vague and questionable public-order charges that could result from a police officer stopping him as he was driving or walking or standing somewhere.

    It was a violation, too, if he was discovered knowingly associating “with other persons on parole, aftercare release, or mandatory supervised release without prior written permis sion from his or her parole agent.” What was the likelihood that Michael would run into other people on parole? The neighborhoods due west of St. Leonard’s, East Garfield Park and West Garfield Park, had the highest incarceration rates in the city, more than six times greater than the national average, and also had the city’s highest percentage of residents returning from prison. Along with mass incarceration, the United States had created a symbiotic crisis of mass supervision. In 1975, there were 143,000 people out on parole in the country. From that point on, however, the prison population took off by nearly 700 percent. Hundreds of thousands of people entering prison each year meant that many more people eventually exited, most of them leaving prison and entering some required form of community control. Some 820,000 Americans are now on parole. Another three million people are on probation. The rise of this supervisory state of nearly four million Americans is unprecedented historically and unrivaled globally. In 2020, one in every sixty-six adults in America was on parole or probation. For Black men, it had been as high as one of every twelve.


    On Michael’s first morning at St. Leonard’s, he met his new roommates, Ray and Robert Jones. Ray was younger than Michael by at least twenty years, but Robert Jones, who went by RJ, at seventy-six, was a decade older, and he was a talker. RJ asked Michael what he thought about breakfast that morning. Michael eyed him warily. RJ had spent forty-one years in prison and won parole only a month before Michael. He spoke in a slow, comic delivery, like he was exaggerating lines in a burlesque. RJ asked Michael whether they should buy Christmas gifts online or at a store. Michael remained cagey.

    “I don’t know, man,” he said. “That’s something you gotta decide.” “I see you’re the silent type,” RJ teased.

    Michael didn’t want to divulge too much about himself. He offered tight hellos to the other men he met over the next few days. He was still figuring out the place. Then later that week, at the halfway house’s Christmas party, he was asked by the staff to introduce himself. Michael stood in front of the group in silence. He uttered his name, adding how long he’d been gone. There were shouts of encouragement. Michael scanned the smiling faces in the room. Michael had told himself countless times in prison that he was getting ready for a moment like this one. He’d recited speeches in his cell, monologues about freedom and human nature, tributes to his perseverance and preparation. But now he was standing at a holiday party, on Chicago’s West Side, amid all these cheerful people. The fact of it walloped him. There was nothing in his life to compare it to. It felt like a miracle. Michael started to talk about how he showed up at St. Leonard’s at midnight and was met by a welcoming party.

    “I never felt so much love and concern about me.” He had served time for killing another person, and yet everyone at St. Leonard’s accepted him. They put him on a pedestal. Michael’s jaw shook, his throat constricted. Heavy tears rolled down his cheeks.

    “You can do it,” a man shouted.

    “Thank you,” Michael managed to whisper. Another former parolee who worked at St. Leonard’s put his arms around Michael. Someone else came over and embraced them both. And then others joined them, add ing to the growing knot of bodies.

    Back in their room, RJ couldn’t stop talking about Michael’s “crocodile tears,” his “performance” at the party.

    “This motherfucker must be able to cry on call,” RJ shouted. “He had that room fired up.”

    “I wasn’t bullshitting, man,” Michael laughed. “That was some real shit. I couldn’t stop crying.”

    Michael’s son was living in Massachusetts, working in a glass factory.

    He sent his father a cell phone, and St. Leonard’s helped Michael activate it. Michael’s three daughters, along with their children and, in some cases, their children’s children, still lived around East St. Louis. The cell phone allowed Michael to reconnect with all of them. He was learning how to be a father, grandfather, and friend. He even reconnected with Joyce, his ex-wife. After decades of no communication, they started talking again.

    St. Leonard’s recommended to its residents that they settle in a while before trying to mend ties with family. That they ask their relatives to be patient. People coming out of prison were fortunate if they still had loved ones who wanted them back in their lives, who needed them. But relatives of the formerly incarcerated could also be demanding, understandably so. They’d spent years raising children on their own, handling every meal, bill, and crisis. Children grew up without a parent, with that daily absence in their life. Parents grew old with their sons or daughters locked away, and the responsibility of their elder care fell to others. For many women making the transition back from prison, the expectations were even higher. They were supposed to be nurturing, maternal, family-oriented; they felt an urgency upon their reentry to prove themselves. The staff at St. Leonard’s preached that residents might not be ready to fulfill those expectations—they needed a little time, and space, to figure out the kind of person they wanted to become, so they didn’t repeat whatever got them sent to prison in the first place. Another formerly incarcerated man who worked at the halfway house counseled Michael, “Don’t build a house on sand, cause sand always sinks.”

    Forty men lived at St. Leonard’s and eighteen women in its nearby Grace House. They all had to complete a three-month core curriculum, with courses five days a week. Classes on managing anger and building healthy relationships. Classes on substance abuse therapy, relapse prevention, and financial literacy. Michael learned how to open a bank account, how to avoid the fees that came with a prepaid debit card. He learned about car loans, identity theft, and the ballooning interest of short-term payday loans.

    Michael took lessons on how to navigate the internet. “I’m in that Facebook,” he said. “Either you plug into the ‘Matrix,’ or you don’t exist.”

    Michael’s favorite class at St. Leonard’s was Reading Between the Lines. They read and then discussed Shakespeare, the Gettysburg Address, Martin Luther King’s “Letter from Birmingham Jail.” For someone who liked nothing more than to share his philosophical musings, the class was a joy.

    Along with mass incarceration, the United States had created a symbiotic crisis of mass supervision.

    One day they were asked to mark up a poem by the Chilean writer Pablo Neruda. The poem was odd. About a child’s foot, and how that foot, being so young and innocent, imagines it can be something other than a foot. That it can be anything. A butterfly. An apple. But the foot goes through life. It steps on the hard ground. It treads on stones and pieces of glass. Everything about the foot’s existence drives home the lesson that, no, a foot can’t fly. No, you are not going to grow ripe and juicy on a tree. It’s into a shoe for you.

    Michael wondered what he could have been under different circumstances. Hadn’t the stones and glass and rough earth of East St. Louis taught him to hustle, steal, and carry a gun? In Reading Between the Lines, he was good at analysis and interpretation. What if he’d been able to go to college? He could have studied literature, history, religion. He could have been a teacher. Or was Neruda saying those dreams were silly? That he was doomed to his fate? A foot is a foot and not an apple no matter what it thinks of itself.

    In April, after four months at St. Leonard’s, Michael was offered an opportunity to stay. Next door to Michael’s dormitory, St. Leonard’s operated a residential building with forty-two single-occupancy kitchenette apartments. Michael moved in to one of these units. He had his own place. His own key. After a half century without it, he now had his own private bathroom. The apartment wasn’t elaborate—just five steps from front door to back window. It was divided down the middle by a wardrobe, the kitchen on one side, his raised bed on the other. But Michael said he had everything there he needed. He had a small table and two chairs. He had a radio tuned to a jazz station. He had a television propped on top of a dresser and a pile of DVDs. He had a row of books next to his bed. He had a leather jacket hanging in his bureau and shoes stacked in boxes. He owned utensils, Tupperware, dishes, a Crock-Pot, and an air fryer.

    Michael told RJ that from his prison cell he’d dreamed all of this. He swept his hand to display the bounty of his new life.

    Michael said, “The soft music, a fireplace, a woman, a nice glass chess set.” RJ pointed out the obvious: there was no fireplace, no woman, and no chess set. Michael laughed. But everything else, he said, had already come true.

    The morning after he moved into his new apartment, Michael packed a knapsack with his ID, birth certificate, and proof of residency and headed east. After the grayness of Chicago’s winter, the spring day radiated with promise. Daisies and tulips peaked out of the hard ground along Madison Street. It felt like a beginning. Michael got on a bus heading to the Loop. He was a parolee. And because he had technically moved, albeit only next door, he had to get a new state ID, with his new address, at the secretary of state’s office, and then he had to register the change with the Chicago Police Department. Those were the rules. Michael followed them to the letter. The trip was an excuse as well to revel in his fluency with the city. Michael had developed a bond with Chicago. He met people there who didn’t know how to find city hall or the main library. Michael had it all figured out. People started asking him for directions. He belonged there. He no longer inserted his bus card backward. He imagined that the people on the bus saw him as just another normal citizen. “When you get to know me,” he wanted to say out loud, “you’ve got a true friend. I am an asset, not a liability. You are dealing with a solid, genuine, and honest person.”

    At the offices of the secretary of state, Michael dropped off his paperwork. Smooth sailing. He left the building and wandered downtown, a moving part of the city’s bustle. He picked up the bus heading south. He had to comply with that 2006 law requiring anyone convicted of murdering a youth to register a change of address with the local authorities. It was just paperwork. In prison, Michael called the guards “police.” Now, as he walked into the city’s main police headquarters, a building with hundreds of cops, he felt no fear. They no longer controlled him. He dropped his backpack onto the conveyer belt to be scanned. He received a tag and a number to wait his turn. He made all the right moves. He heard his name and went to a desk and handed an officer his papers. The officer greeted him warmly and asked Michael to please wait. Michael waited.

    The officer was having trouble finding Michael in the system. When more time passed, Michael began to wonder. Needles of heat pricked his neck. He twisted in his seat. Behind him, in his periphery, two cops hovered. Were they looking at him or just standing there? Did their bodies stiffen? Michael admonished himself. It was the old paranoia. The suspicions he’d needed in prison to survive. He hadn’t shaken them yet. But he was getting there. The penitentiary mindset came less frequently. He’d been institutionalized so long that he sometimes couldn’t read the signs in the free world. The officer at the computer looked up. “I’m sorry to inform you, Mr. Henderson, but you’re under arrest.”

    Michael thought the man must be joking. He wasn’t. The two officers behind Michael moved in on each side of him.

    “I know this isn’t real.” Michael gasped. The room was suddenly spinning. It had to be a mistake. He’d made no false moves. “Please, please, I’m not the one,” he cried. It made no sense. There had to be a mix up. Why would Michael come to the police station if he’d done something wrong? The officer said he had no explanation. All he knew was the computer said there was a warrant out for Michael’s arrest.

    Michael told the man that he was sixty-seven years old. That he just got out of prison after forty-six years. That life was wonderful. He couldn’t go back.

    “I just need some help in correcting this error. Someone made a very egregious error.”

    The officer said his hands were tied. Nothing he could do. He did allow Michael to look up a couple of numbers on his cell phone. Michael called Marjorie Moss and the office at St. Leonard’s. No one picked up, and he left messages.

    Before Michael was booked, an officer who processed him was surprised that Michael wasn’t in the gang database, that he wasn’t hooked up and didn’t have a long string of arrests.

    “You are totally not of this era. You don’t even exist in our computers. You don’t have any history,” the cop said.

    Officers confiscated Michael’s backpack and wallet. They took his shoelaces and cut out the cinches on his jacket. They locked him in a cell.


    From Correction: Parole, Prison, and the Possibility of Change by Ben Austen. Used with permission of the publisher, Flatiron Books. Copyright © 2023 by Ben Austen.

    Ben Austen
    Ben Austen
    Ben Austen is a journalist from Chicago. He is the author of High-Risers: Cabrini-Green and the Fate of American Public Housing, which was longlisted for the Andrew Carnegie Medal of Excellence in Nonfiction and named one of the best books of 2018 by Booklist, Mother Jones and the public libraries of Chicago and St. Louis. A former editor at Harper's Magazine, Ben is the co-host of the podcast Some of My Best Friends Are. His feature writing has appeared in the New York Times Magazine, GQ, Wired and many other publications.

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