As he watched CNN from inside the federal correctional complex in Coleman, Florida, Rufus Rochell couldn’t suppress his joy at the news of Conrad Black. His old friend, the media tycoon with whom he shared a dorm years ago, had received a pardon from President Donald Trump. Surely this meant that his time would come soon.

Maintaining a level of optimism has been Rochell’s primary objective for 31 years now. That’s how long he’s been behind bars. He’s the byproduct of a bygone era when being tough on crime was viewed as politically savvy, when a man like him—a convicted drug dealer—could receive a sentence of 40 years and no one would think twice about the human cost.

But that was then. Now Trump himself was waking up to the injustices in criminal sentencing and surely Conrad Black, a Trump buddy, would help right his wrong.

“This is your old and forever friend Rufus Rochell, sitting here in prison for the many of years,” he wrote Black the day after the pardon was announced. “I saw on CNN today where the great president gave you a PARDON, that you truly and sincerely deserve. It couldn't have happen to a better person... you now can go on with the family and be the great man you are and continue your journey to fighting for others like myself and other deserving ones that many have forgotten.”

Black was back in Canada, where he was born and had built his business empire, when his pardon was announced.

More than a decade ago, he had been found guilty of mail fraud and obstruction, charged with swindling his company of some $60 million. And in 2011, he had leaned on Rochell to help him secure early release by writing a letter attesting to his character.

Black’s sentence was ultimately shaved down on account of good behavior. And in the seven years after he was sprung from Coleman, he had resumed his status as a member of the upper crust and a commentator on world affairs.

He became an outspoken critic of America’s criminal justice system, owing in large part to his own experience. He also was a very public Trump booster, writing a book titled: Donald J. Trump: A President Like No Other.

The sequence of events led to questions about the judicial merits of the pardon. But when I reached out to Black shortly after the pardon was announced, it was with a different question in mind: Now that his record was expunged, would he help his old friend Rufus Rochell, as Rochell had done for him?

“I’m happy to write a letter of support for Rufus if they tell me where they want it sent,” was all he said.

When Rochell and I last talked on the phone this past Friday, he said he’d not yet heard back from his jailhouse friend.

I first heard of Rufus Rochell a year ago. After President Obama left office with a historic push to wipe away overly harsh drug sentences, I wanted to profile someone who hadn’t gotten in under the wire and now was staring down four, potentially eight, years with a president who branded himself a throwback on crime.

Rochell, 67, was the first case sent my way. And for good reason. As I came to discover, he is preternaturally congenial. His emails were always peppered with phrases like “GOD BLESS” and well wishes for a family member. When he got to talking on the phone, he would not stop. Attorneys who worked with him described the trepidation they’d feel when “No Caller ID” flashed on their phone—knowing they were in store for a 15-minute conversation (Rochell always used the maximum allotted minutes) and feeling pangs of guilt that his call money was being spent on them.

But human interaction was what kept Rochell functional. He mentored fellow inmates, became a prolific letter writer, and posted book and movies recommendations to Facebook, often ones dealing with race or the criminal justice system. Mainly, he spent his time searching for his ticket out.

“He somehow got my phone number,” said Amy Povah, president of the CAN-DO Foundation, a group that advocates for greater clemency in the criminal justice system. “At first I tried to beg off. But he was so persistent and humble that I couldn’t ignore him. I said these calls are very expensive and money doesn’t come easy in there. But he just melts your heart.”

Rochell grew up in Dania Beach, Florida, in what he called a “close-knitted family area.” He described his childhood as “regular.” He played ping pong, went to beaches, and fondly recalled his days in school. His mother was loving and beloved, often spending her time baking meals to feed the hungry in the neighborhood.

But his childhood was hardly idyllic. Those beaches were segregated. So, too, were the schools at first. And his biological father, George, would drink.

“He was not an abusive man,” Rufus told me. “He was just someone during those years who loved alcohol and his personality changed when he was drinking. He loved his kids, that was a fact. But I learned during those years how alcohol destroys a relationship.”

Eventually, his parents divorced and his mom met another man, a pastor named Samuel Clark, dubbed the “Crying Preacher” by his congregation. When Clark moved in, things changed for the better. “He was the part of our life that was missing,” said Rochell.

Rochell was a shy but popular kid. He played golf, which he learned by caddying the nine-hole course not far from where he grew up to help make money for his family. He also rummaged through dumpsters, looking for copper, brass, and aluminum to sell so that he could help his mother purchase school clothing.

After graduating high school, the trouble started. He rented a car, took it for a joy ride, and just decided not to return it. He liked nice cars, his friends told me. And at age of 20, he was caught stealing one. After that, he was found guilty of larceny, theft, and possession of marijuana.

Rochell got a job painting houses and when he was snubbed for a promotion, he turned to selling drugs as a way to make money. It was small-time, he insisted. Dime and nickel bags of weed. Twenty-five-dollar bags of powder cocaine.

At this point, the story becomes fuzzy. Rochell was reluctant to give specifics on the arrest that landed him at Coleman. But through it all, he insisted on one thing: his incarceration was the byproduct of a remarkable confluence of unfortunate events.

In the late '80s, the University of Florida was rocked by allegations that its athletes had been buying and using cocaine. The country was still coming to grips with the tragedy of Len Bias, the college basketball star who died from a drug overdose shortly after being drafted by the Boston Celtics, and university administrators and law enforcement agents pledged to get to the bottom of what was happening at U of F.

One tip they followed was that the dealer for the basketball team went by the nickname “Ice.” The tip led to Willie “Ice Bird” Reed, his brother Terry Reed, and three other men, including Rochell, Willie’s cousin. Rochell said that he was at a grocery store buying items for his fiancée’s birthday the day in April 1988 that he was pulled over by the City of Gainesville Police and held on the side of the road for two hours.

Eventually, they took him to headquarters, where they told him he was being busted for selling drugs. He pleaded his innocence and continued to do so when he was charged later that month and throughout his subsequent court proceedings, which he said were marred by the fact that his lawyer was living in Miami and the jury being almost exclusively white.

Rochell was found guilty for conspiracy to distribute 50 grams or more of crack cocaine and possession of more than 50 grams of crack. To this day, he insists he never sold crack. But for purposes of the sentencing guidelines, the judge determined that he was tied to a conspiracy to distribute 24 kilos of it.

In October 1988, Rochell was given a sentence of 420 months with no chance of a sentence reduction. Shortly thereafter, he was given an additional 60 months related to a prior drug conviction, in which he’d encouraged a witness to lie. He was 36 years old.

Roughly a year later, six men were found guilty of conspiring to sell drugs to athletes at the University of Florida, including the basketball team’s former star player Vernon Maxwell. Among them was Eugene Scott, who went by the nickname “Ice.”

Rochell entered prison staring down a 40-year sentence with no chance of parole.

He was, at the most basic level, the outcome of an ideology that held that mass incarceration was the best way to deal with drug-related crimes.

On a human level, he was broken. When he was sentenced, his stepfather, the pastor, asked the judge for mercy. His pregnant fiancée Michelle left the courtroom in tears.

“I was hurt, upset and humiliated. I felt my world had come to an end,” Rochell told me. “It was a horrifying time knowing that I would never get a chance to marry Michelle and seeing the expression on her face as if our entire life had just been shattered…. You always wanted to be a good father to your kid. You didn’t want to be a deadbeat dad.”

Those early months were filled with a sense of desolation. But then a man named Bernie came to him and explained that the while past was inalterable, the future was not. Gradually, Rochell’s disposition improved.

He took classes in photography and Spanish, and became involved with My Brothers 2 Keep Ministry. Mark Davis, a fellow inmate, recalled how Rochell taught himself drug crime-related law and served as the de facto “jailhouse lawyer”—charging only a bag of coffee and $15-20 worth of food for his services. One day, in 2005, Rochell started asking fellow inmates for a single dollar to help support Hurricane Katrina relief efforts.

“To me,” Davis said, “he was the only wise man that I knew there. To be honest with you, no one could compare to Rufus.”

Years passed. Routines hardened. And then, in March 2008, something highly unusual happened. A black SUV arrived at Coleman and the prison staff closed down the entire floor in Rochell’s compound. An elderly man was brought in.

It was Conrad Black.

Black was, to put it mildly, not like the rest of the inmates. For starters, he had been a member of the House of Lords, ran one of the largest English-language newspaper empires in the entire world, and owned a luxury Park Avenue apartment, a multimillion-dollar London townhouse and a $30 million Palm Beach mansion. He had been sent to federal prison for fraud and embezzlement, which encompassed such excesses as charging his company for his wife’s $62,000 birthday party.

And yet he and Rochell hit it off. They both worked in the education department, Rochell as a law clerk and Black as a tutor helping inmates study for their GEDs. They had conversations about history and education. And they found humor in the subtle absurdities of prison life, such as the thunderous rain that fell whenever inmates were asked to report for lawn duty.

“ He is simply an optimistic and brave person who thinks life is basically good and that perseverance is rewarded. ” — Conrad Black on Rufus Rochell

“My impression was that Rufus had come from a very disadvantaged condition and in an era when there was a good deal more segregation in the South than there is now, or was in the prison, where the warden and many of the personnel were African-American. So it was not as arduous for him as for some people who suffered an extreme diminution of quality of life,” Black told me. “Apart from that, he is simply an optimistic and brave person who thinks life is basically good and that perseverance is rewarded.”

Months into Black’s time at Coleman, Rochell got word that his biological father was dying. George Rochell came to the prison to say his goodbye. The two sat outside on the patio together. By then, Rufus had made peace with his father’s drinking and George had given that drinking up. Still, he asked his son for forgiveness.

“All I could say to dad was, ‘We will leave it in God’s hands,” Rufus said.

When George died in March 2010, Rufus said he was broken all over again, processing a pain that he couldn’t quite comprehend. It was Conrad Black who came to his room to sit down and pray with him.

“He told me if there was anything he could do for the family please feel free to let him know, because he understood what I was going through, because he lost his dad a while back,” Rochell recalled. “We were the best of friends.”

In the summer of 2010, Black was granted bail after the U.S. Supreme Court ordered a lower court to review its initial decision in his case. As the matter moved through the judicial system once again, he left Coleman, and did not return.

But he continued to stay in touch with Rochell. In May 2011, Rochell wrote an email to Black in which he told him that he was his “hero.” Black wrote back three days later: “I think of you often and am grateful yet for your warm reception of me there. Never give up; there are better days ahead.”

In those days ahead, Rochell would come to Black’s aid. Not everyone in Coleman had appreciated Black’s presence there. It had been reported that he treated other inmates as servants and asked for special treatment. With Black’s sentencing hearing coming up, his legal team asked Rochell to write a note rebutting those allegations.

Rochell cheerfully did so.

The copy of the letter, which Rochell provided to me, showed a genuine affection for a man he considered a mentor and a friend. But there was a subtext to it that was quite sad. Rochell saw Black’s freedom as a gateway to his own—a chance for someone to leave Coleman, evangelize about the injustices of the criminal justice system and bring solace to those he’d left behind.

“ We love and appreciate this gentleman and we ask your honor to allow him to remain a free man where he will be able to turn other lives around, just as he did for those of us behind bars. ” — Rufus Rochell on Conrad Black

“We love and appreciate this gentleman and we ask your honor to allow him to remain a free man,” the letter read, “where he will be able to turn other lives around, just as he did for those of us behind bars.”

Rochell’s time in prison, I soon discovered, was consumed with trying to find people on the outside who could bring him relief. I was one of them.

In the late 1990s, he wrote the TV host Tavis Smiley about his case and Smiley even wrote back. In 2002, he connected with a man named Edward Green who was—according to the letter he wrote to the U.S. pardon attorney on Rochell’s behalf—a classmate of Joe Biden’s. In 2008, Rochell got his case noticed by someone in Sen. Bill Nelson’s office, who flagged it for a public defender. A year later, Rochell wrote Attorney General Eric Holder. That same year, he attempted to get his sentence reduced on grounds that the sentencing guidelines had changed. Nothing came of any of those appeals.

But Rochell just kept at it. His case was picked up by lawyers associated with the National Association of Criminal Defense Lawyers during the Obama administration's second-term push to commute more drug-related sentences. His representative, Margaret Russell, put together a petition noting that Rochell was not a violent offender, had good conduct in prison, and had offers of housing and employment on the outside.

Again, it wasn’t enough. “There were just too many cases that if anyone had anything that was a question, their application ended up in the question pile as opposed to the grant pile,” said Russell, citing Rochell’s obstruction charge as the main problem.

When Obama left office and Trump came in, the conventional wisdom was that people like Rochell were now firmly out of luck. But Rochell, who’d applied for clemency three times by then, just adjusted to the times.

During one of our phone calls, my jaw dropped when he casually asked if I could put him in touch with Kim Kardashian, confident that the reality TV mogul could do for him what she had done for Alice Marie Johnson, a 63-year-old woman who had been serving life in prison for a nonviolent drug conviction before Trump granted her clemency at Kardashian’s behest. He had plans to invite her to speak before at Coleman and later forwarded me an email he’d sent to her lawyer.

“First and foremost,” it began, “thank you Mrs. Kim Kardashian-West for taking the initiative and caring heart to involve yourself in criminal justice reform.”

Rochell’s latest ray of hope may, in the end, be his best. The passage of the First Step Act in 2018 reduced the disparity in crack and powder cocaine sentences, increased “good time credits” that inmates can earn, and gave inmates “earned time credits” for getting involved in vocational and rehabilitative programs.

In one of our last email exchanges, Rochell seemed positively enthused by the legislation and praised Trump and his son-in-law Jared Kushner for seeing it through. Though he did not have a lawyer, he said he had filed his own motion under the act.

“I feel strongly I will get an immediate release very soon,” he proclaimed. “Thank God!”

And, perhaps, that’s how this story will end. Perhaps it will be legislation signed into law by a tough-on-crime president that secures his release. Perhaps he won’t need an intervention from Conrad Black or Kim Kardashian. Perhaps he will finally get to spend a single day outside of prison with his daughter Antoinette after 31 years gone.

But if it is to be this way, the ending won’t be a universally happy one. Too much life has been lost and missed for it to be that.

In September 2017, Rochell’s stepfather, the man who had given him the part of his life that he’d been missing, died. Half a year later, his mother Mattie Clark, who prepared meals for the hungry, passed, too.

“I wish that I had parents to call, or to send birthday cards to let them know how much I love them,” he wrote me. “I never forget what my mom used to tell my brothers, my sister, and me whenever we made a mistake and it disappointed her in any way. She would say, alright now, ‘You’re going to miss me when I’m gone.’ And we do. I wish I could tell her how much I love her one more time, just one more time.”

The pastor’s death was due to Parkinson's and diabetes, Rochell told me. His mom had died due to complications stemming from a stroke. But he suspected it was more than that. Her will to live, he offered, had vanished a bit along with her second husband. He did not get a chance to say goodbye in person. The last time he’d seen her was nine months prior.

“I kept telling her I would be home soon,” he said. “I tried but came up short.”