Life Outside

His First Day Out Of Jail After 40 Years: Adjusting To Life Outside

Smartphones, the Internet, job-seeking. For prisoners released after decades behind bars, the modern world is difficult, confusing, and still better than anything ‘on the inside.’

01.03.15 11:55 AM ET

I meet Otis J. the night he arrives at “The Castle,” a West Harlem halfway house for newly-released convicts. Sprung from prison in August after doing 40 years for attempted murder, Otis shows up with a laundry bag containing his life’s belongings. I notice he moves at a slightly slower pace than everyone else, and keeps his gestures compact. I imagine it’s partially a by-product of spending the bulk of one’s life living in a 70-square-foot cell, and partially due to the fact that in prison, sudden moves tend to get you shanked, pepper-sprayed, or both.

A kindly man with a downy white beard and a gentle manner, it’s almost as if the 69-year-old Otis somehow willed his senses into dulling down, just to survive 40 years in the flat, featureless prisons of New York State. He had resigned himself to the fact that he’d die behind bars, so he adapted. And as with anything one does for four decades, it’ll probably take a little time to undo it. The prison diet didn’t agree with him, so says he never ate much. I ask what he had for a first meal when he got out, if cravings had ever turned a cellmate into a rack of ribs or a cheesesteak like in a Bugs Bunny cartoon, but he just shrugs and says he’s “not really that interested in food.”

Otis, who tells me he was called “Saladin” on the inside, has taken an almost tragically circuitous route in getting here. Denied parole nine straight times, he insists he is innocent of the crime for which he was convicted. He says he was arrested at a park on 119th Street, and the crime happened a few blocks away, at 116th & 7th, that his conviction was a case of mistaken identity. Otis says he was wearing a tan jacket similar to one described by witnesses.

Barry E., Otis J. and Stanley Richards chat in the dining room of the Fortune Society, Dec. 31, 2014.

Sarah Rogers/The Daily Beast

Whether that’s true or not, taking responsibility for one’s crime is a crucial part of being paroled. By maintaining his innocence and refusing to admit to something he says he didn’t do, Otis fell into a catch-22 known as the “parole paradox.”

“They told me on my sixth hearing, ‘If you say you did the crime, we’ll let you go,’” he says. “I turned it down.”

Ultimately, like 97 percent of America’s 1.2 million prisoners, Otis was eventually given a release date. But, as he was about to leave the cold confines of Upstate New York’s notorious Attica Correctional Facility last winter, prison officials told him he was wanted in New Jersey on a juvenile shoplifting charge he had picked up when he was 16. After serving an additional eight months at South Jersey’s Bayside State Prison for that, Otis, who had $40 in gate money but no place to live, was released to the Bellevue Men’s Shelter in Manhattan.

“It was like a medium,” he says, and quickly clarifies that by this, he doesn’t mean a psychic, but a “medium-security prison.” Shelter staff arranged for Otis to stay in a small two-man room rather than out among the general population in the main hall, so that sleeping outside a cell for the first time wouldn’t be unnecessarily discombobulating. It was one of the few things that felt familiar to him after being away from the outside world since 1975.

“I saw all these people on the street talking to themselves, I thought I was bugging out,” he says, shaking his head and chuckling softly at the memory. “Someone finally told me that they were talking into earpieces, they were phones. So then I started thinking that there were secret agents all over the place, because the last time I was in society, those were the only people who had equipment like that. I stood on the corner for two hours, semi-hypnotized, just frozen.”

Identity issues seem to have dogged Otis since his troubles began. When he was first incarcerated, he says some sort of paperwork snafu had him imprisoned under two different, but similar, names. Once that was cleared up, his prison file, which contained his birth certificate, social security card, and so forth, went missing during one of the myriad transfers every long-termer can expect. And so, he says he left prison without proper ID, just his release papers and the “dress-out gear” he was given by the state. Otis eventually got a copy of his birth certificate, which he remembered being at least partially sufficient for a state non-driver ID, but when he took it down to the DMV, he found out the documentation you need for such things these days is a lot more extensive than it used to be, and he was turned away.

Barry E. poses in his bedroom at the Fortune Society. Barry says he snagged a one bedroom in the halfway house due to luck and timing, Dec. 31, 2014.

Sarah Rogers/The Daily Beast

The grim instability of shelter life is hardly a recipe for success under the best of circumstances. Fortunately, after Otis had been at Bellevue for a few months, a former prison buddy with connections at the Fortune Society, the New York City nonprofit that runs the Castle, was able to get him a bed there.

Fortune’s Castle was opened in 2002 and has helped roughly 1,200 people since opening its doors. The building used to be an all-girls school, and when it was initially purchased by Fortune it was dilapidated. Millions of dollars in renovation later the building is gorgeous—Clean, well-kept, organized. The resources were what you might expect: Dining room, a media center, a library, a TV room, a meeting room, a computer room. Stanley Richards, Senior Vice President of the Fortune Society, gave a tour along with a few residents. Richards’ pride in Fortune and its residents is undeniable—he was eager to show me the building, he hugged passersby in the hallway, and whenever the word “community” came up, he and the residents within earshot smiled and nodded in unison.

Richards explained that around 100 residents stay at Fortune each year, but residents don’t adhere to a specific residency schedule. “There’s no time limit,” resident Barry E. added. “It’s not a one-size-fits-all.”

Barry showed me his room—a one bedroom with a killer view of Riverbank State Park and the Hudson. He assured me that having your own room wasn’t common at Fortune, that he was blessed with timing and luck. Rooms vary from four residents to a room to one. There’s also “emergency” rooming for new arrivals, which eases residents into sleeping outside of a cell.

Stanley Richards, Senior Vice President of the Fortune Society, poses in a stairwell of the Castle, Dec. 31, 2014.

Sarah Rogers/The Daily Beast

Otis tells me he earned two associate’s degrees on the inside, and worked in the prison hospital’s AIDS ward. He got a suit for job interviews through one of those “dress for success”-type programs young white guys donate their old clothes to, and though it’s not a perfect fit, it looks pretty sharp. He’s still chasing down that ID—without it, he can’t work—but now that he’s not spending his time on things like keeping other shelter residents from stealing his shoes, he’s a lot closer to getting it.

The odds of getting re-arrested are a lot slimmer if a person has a job. But almost to the man, the first thing every ex-con tells me is how hard it is to find work. One Fortune resident who did 25 years on a homicide conviction, tells me he’s hoping to get a so-called “Certificate of Relief” from the Parole Board in the next year or so, which would remove many of the legal restrictions barring felons from certain occupations. However, legal issues are only one of the things standing between an ex-prisoner and a job. Having a criminal record can reduce the likelihood of getting a callback or job offer by 50 percent. And after prison, where inmates don’t have access to the Internet, many quickly realize that even sending out a resume is nothing like it used to be.

Sam H. spent 32 years in prison for robbery and felony murder, though one could be excused for taking the deeply intelligent 53-year-old for, say, a PhD advisor. In 1983, Sam, who had never been in trouble before, agreed to help two friends pull off a robbery. They selected an “easy mark” who turned out to be an off-duty NYC Housing Authority cop named James Carragher. Gunfire was exchanged and Sam, who was unarmed, was wounded. Officer Carragher was also wounded. Sam survived, Officer Carragher didn’t. Sam wasn’t the shooter, but only Sam went to prison. He was 20 years old.

Sam was first eligible for parole in 2006, but because he was involved in a cop-killing, the parole board wouldn’t let him go. The “nature of the crime” was too serious to release him, they said. He earned a bachelor’s degree behind bars, then a master’s. He started the “Stop the Violence Peace Initiative” at Sing Sing, and raised $10,000 for the prison’s Family Center, which helped buy supplies for children whose parents were incarcerated there. Letters poured into the parole board’s offices from people who supported Sam’s release, including 20 correctional officers that had supervised him to the district attorney who prosecuted him. Still, he was denied parole seven times. On his eighth try, more than three decades after he went in, the parole board finally voted to release Sam. And he found a very different world than the one he left.

Samuel H., Stanley Richards, Barry E., and Otis J. pose outside of the Castle in West Harlem, Dec. 31, 2014.

Sarah Rogers/The Daily Beast

Back when Sam went upstate, job searches required nothing more than a typewriter, some paper, and the classifieds. When he was finally set free this past September, he found himself using technology that didn’t exist when he went in. Classified ads have largely been replaced by Craigslist,, and the like, and since safety issues preclude prisoners from accessing the Internet, the past three decades of progress can easily pass one by.

Get The Beast In Your Inbox!
By clicking "Subscribe," you agree to have read the Terms of Use and Privacy Policy
Thank You!
You are now subscribed to the Daily Digest and Cheat Sheet. We will not share your email with anyone for any reason

“It’s like the Stone Age when it comes to computers on the inside,” Sam tells me. “Sending out resumes when you get out—figuring out how to download the document, attach it, email it, et cetera. Guys doing 25, 30 years, they don’t stand a chance.”

Most ex-inmates don’t think to ask for help, he says. It’s not a habit people develop in prison, explaining that “you could be deemed ‘weak,’ or ‘vulnerable.’” For some, supermarkets are overwhelming. After years of little or no choice in what you eat, wear, and buy, imagine suddenly having to decide between 30 different kinds of shampoo, or potato chips, or toilet paper. A man who did a 14-½-year stretch tells me he’s been out for 11 years and still can’t go grocery shopping alone. He did ask for help, and now he and two other ex-cons make weekly trips to the Fairway on 125th Street as a team, sharing one cart and splitting the decision-making three ways.

Waking up at 5 a.m. for the “count” is a hard habit to break, and after being surrounded by people 24 hours a day, seven days a week, for years on end, being alone can be unnerving. Paying for things is a lot different than it used to be, too. Debit cards take some getting used to, and public assistance, which many newly-released prisoners rely on to survive, is now largely doled out this way. After 22 years in prison on first-degree robbery charges, Larry C. knew he’d have to get accustomed to the subway system all over again. The fare had doubled, from $1.25 to $2.50, while he’d been away, and MetroCards had replaced tokens. Swiping one through a subway turnstile came easily, but figuring out how to dip the card into a bus’s farebox stopped him cold. When the line behind him got too long, the driver showed him how to do it, commenting archly, “I see you don’t ride the bus very often.” One elderly ex-con told me it took him a while to get used to the smell of ladies perfume again, after years of little contact with the opposite sex.

Another former inmate describes tasting fried chicken again after a decade-and-a-half of institutional food, saying the feel of the rich meat in his mouth was “totally surreal.” The taste of metal cutlery after years of plastic can also taste funny. Prisoners in New York State are released back to their counties of conviction, so if you were locked up in Brooklyn, you’re going back to Brooklyn. Familiarity can be a stabilizing force, though it can also mean trouble—especially, if like many parolees, you fall in with the same crowd that led to your incarceration to begin with.

You’ve got to be on your best behavior when you’re on parole, and so does everyone you’re with. Even being around someone smoking a joint is a violation. The recidivism rate in New York State is roughly 40 percent, but Fortune residents go back to prison at a rate of less than 1 percent—the lowest in the city. It’s easy to understand why one wouldn’t want to be sent back to prison. But a drug-dealer-gone-straight from the Lower East Side sums it up best, saying, “The best day on the inside—when I had a hot visit and I’d put on my best Muslim cologne, you know, my Muslim oils, and I had my greens creased seven different ways by putting them under the mattress of the biggest guy’s bed—the best day on the inside will never, ever be anywhere near as good as the worst day on the outside.”