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10 Tales Of Crazy Convicts In The US Prison System

Nolan Moore


While the US is “the land of the free,” it paradoxically has the world’s largest prison population. According to the BBC, 724 people per 100,000 are locked up in the American correctional system, which is a shocking statistic.

With all these convicts passing through the Big House, American’s prisons are brimming with peculiar people from all walks of life. From country bands to candymakers, the US prison system is jam-packed with fascinating figures and crazy characters, all with unique stories.

10Roy Smith
The Strangest Family Reunion

Roy Smith barely remembered his father. A drug dealer and abusive husband, Roy’s dad disappeared when Roy was a kid. What he knew about his old man—Roy Milton—was all negative, and that’s why he swore he’d never follow in his father’s footsteps.

Perhaps that’s why Roy attended college and became a pastor. But his life fell apart after buying a new building for his church. Without Roy’s knowledge, his trusted broker cooked the church’s books to get the loan for the building. When the FBI showed up, Roy’s signature was all over the paperwork.

Convicted of mortgage fraud, Roy was tossed into federal prison for 15 months. But when he arrived at the penitentiary, things took a bizarre twist. His new cellmate was a guy named Roy Milton. Yes, that Roy Milton. Pastor Smith was going to spend the next 15 months with the dad he never knew.

Naturally, things were weird at first. While they didn’t fight, they weren’t best buds, either. Roy even called his dad “Mr. Milton.” But things changed when Roy’s father revealed a folder full of newspaper clippings. Whenever Roy had appeared in the newspaper, Mr. Milton had snipped the article, tucking it away in his improvised scrapbook. Even though he was behind bars, Roy’s dad had kept up with his son’s life.

Suddenly, the two men were talking about their past experiences, and Roy even asked the tough questions like, “Why did you leave?” While he never got a straight-up apology, their relationship was thawing out. By the time Roy was released, he was calling his father “Dad.”

Three years after the pastor was paroled for good behavior, his father was released as well. In 2009, the two reunited. At last, father and son were together in the free world, their relationship saved by the strangest family reunion ever.


9Daniel Genis
The Writer Who Bought Souls

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Photo credit: Burton1978

The son of a respected Soviet writer, Daniel Genis came from a privileged background, with celebrities like Mikhail Baryshnikov and Kurt Vonnegut attending parties at his home. After graduating from NYU, Daniel became a Manhattan literary agent. But despite his cultured upbringing, Daniel was a heroin addict who owed his dealer $5,000.

Desperate to repay his loan, Daniel started mugging people, apologizing profusely the entire time. Eventually, he was caught and sentenced to 12 years. But during his time in prison, Daniel had some wild “adventures.” He met the murderer who inspired The Amityville Horror and had a front row seat to a race riot. He taped magazines around his body to survive a stabbing and once convinced his fellow inmates to sell him their souls.

That’s right, their souls.

During his stay at a medium-security prison, Daniel was living on $100 per month, meaning he could buy more goods from the commissary than other convicts. That also meant people were constantly borrowing his coffee. Growing irritated, Daniel solved the problem with some peculiar paperwork. Whenever a prisoner asked for coffee, Daniel presented the inmate with a contract. Sign on the dotted line, and you’d get a cup of joe . . . in exchange for your soul.

As each inmate only had one soul, this was the last cup of coffee they could ever get from Daniel. The strategy worked well until a hyper-religious prison official accused Genis of committing an “unauthorized exchange” and threw this modern-day devil into solitary for 90 days.

When he wasn’t collecting souls, Daniel devoured books. During his 10 years in prison, he read a whopping 1,046 titles, including prison memoirs like The Autobiography of Malcolm X and biographies of famous dictators. A rabbi encouraged him to study Josephus, and a meeting with a child molester inspired him to read Lolita.

Daniel even read the heavy stuff like Infinite Jest and In Search of Lost Time. He wrote his own alt-history novel entitled Narcotica, and when he needed to concentrate, he’d drug his yappy cellmate.

Finally, Daniel was released in February 2014. These days, he works as a journalist, writing for places like Vice and Deadspin. As for his reading life, The New Yorker reports that Daniel hasn’t picked up a single book since he got out of jail.

8Robert Hillary King
The Man Who Makes Freelines

Back in the 1970s, Louisiana’s Angola State Penitentiary was known as “the bloodiest prison in America.” This understaffed slammer saw over 250 stabbings between 1971 and 1973 and was home to a thriving sex slave trade. But three prisoners who were sick of the system decided to fight back.

Robert Hillary King (aka “Robert King Wilkerson”), Herman Wallace, and Albert Woodfox were known as the “Angola Three.” The trio met inside prison, formed a chapter of the Black Panther Party, and campaigned for prison reform. They led work strikes, launched hunger strikes, and did their best to make a difference . . . until a guard named Brent Miller was murdered with a lawn mower blade.

The Angola Three were immediately suspected even though King wasn’t in Angola at the time of the killing. While the evidence was incredibly flimsy, Wallace and Woodfox were convicted of the crime, and all three were tossed into solitary confinement. Robert King spent 29 years cut off from the world. So how did he keep his sanity?

He made candy. Whenever he could, King would save his milk, margarine, and sugar rations to create pecan pralines. The guards loved King’s candy, so they kept him well-stocked with pecans as long as he passed out free samples. King baked the pralines with an improvised oven made of fruit cans and burned toilet paper. The man was inventive.

King nicknamed his candy “freelines,” and whenever possible, he shared them with the death row inmates. When King was released in 2001, he traveled the world, lecturing colleges and government institutions on the injustices of the US prison system while campaigning to free his friends.

But he never stopped making freelines. King often brings his candies to political events and fund-raisers. After Hurricane Katrina, he even cooked up a few pralines for the rescue workers. Most importantly, every candy comes with a special wrapper that reads: “Free the Angola Three.”

Herman Wallace passed away after serving 41 years in solitary. Albert Woodfox is still in Angola, having served 45 years as of 2015.



7Curtis Carroll
The Con They Call ‘Wall Street’

Born into a family of crack addicts, Curtis Carroll had a pretty rough life. He fell in with a gang by age 11, and he was arrested at 17 for an Oakland robbery gone horribly wrong. Convicted of murder, Curtis was sentenced to 54 years to life in San Quentin. But while prison often breaks young men, Curtis turned his life around . . . while making quite a bit of cash.

Curtis was illiterate when he landed in the Big House, but he quickly learned to read. One day, Curtis started reading the business section of the newspaper. Intrigued, he began studying the stock market, and his mind was blown. In an interview posted on KitchenSisters.org, Curtis said he just “couldn’t believe that this kind of access to this type of money could be accessible to anybody.”

Soon, Curtis was reading every newspaper he could find, gathering info on CEOs, analyzing companies, and predicting whose stock would rise or fall. Curtis began filing thousands of these articles in envelopes and referencing them before calling home and having someone in the free world buy stocks in companies like Facebook or American Apparel.

“I’m in prison,” Curtis explained on KitchenSisters.org, “but I’m on just the same playing field as Warren Buffett. I can pick the exact same companies. I can’t buy as many shares. But technically we’re just the same.”

Evidently, Curtis is so good at picking stocks that he’s known around the slammer as “The Oracle of San Quentin.” Curtis also teaches financial classes, helping his fellow inmates learn the value of retirement savings, cost control, and diversification.

For years, Curtis was teaching classes by himself, but recently, he’s found an unlikely ally. Every Thursday, the con nicknamed “Wall Street” teams up with Zak Williams, financial expert and son of comedian Robin Williams, to help inmates learn investment strategies and prepare for their future as free men. The two teachers provide all sorts of helpful tips, including Curtis’s number one rule: No matter what, don’t get greedy.

6The Goree All Girl String Band
The Felons With Fans

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Photo credit: cowgirlprincess

About 6 kilometers (4 mi) outside Huntsville, Texas, the Goree State Farm for Women in the 1930s and ’40s was an all-female penitentiary where inmates farmed and made clothes for jailbirds across the state. However, Reable Childs—convicted of convincing her lover to murder her husband—wanted bigger and better things. She’d always wanted to become a singer, and she desperately wanted out of prison.

At that time, one of the most popular radio programs in Texas was Thirty Minutes Behind the Walls, a variety show recorded inside Huntsville prison. The performers were prisoners—felons who sang, put on comedy routines, and gave testimonials. If she could get on the show, Reable realized she would have a chance to sing and get out of prison.

Texas governor Wilbert Lee “Pappy” O’Daniel (who strongly resembled Charles Durning’s character in O Brother, Where Art Thou?) was a fan of the program and a big believer in passing out pardons. Perhaps Reable could impress the governor and win her release or, at the very least, escape the daily grind of prison life through performing.

After rounding up seven other inmates convicted of crimes ranging from drug charges to cattle rustling, Reable started the Goree All Girl String Band. The women learned how to play a whole host of instruments, from steel guitars to bass fiddles. One lady even learned to yodel, and they used any spare time to design their own cowgirl outfits.

The band gave its first performance in July 1940 and was an immediate hit. The girls quickly became regulars on the show, and soon thousands of fan letters were pouring into the prison. According to Texas Monthly writer Skip Hollandsworth, they were the “Dixie Chicks of their day.” Thanks to the Goree Girls, Thirty Minutes Behind the Walls gained four million new listeners. The women toured the Lone Star State, meeting influential figures and performing at rodeos and festivals.

Best of all, Reable’s scheme worked. By 1944, almost all the Goree Girls were released from prison. But as the original members were replaced with new faces, people stopped listening to Thirty Minutes. And instead of capitalizing on their popularity, the Goree Girls abandoned their musical careers after leaving prison. Instead, they tried to create normal lives while keeping their lives as convict celebrities a secret.

5Carlos Cervantes And Roby So
The Men Who Drive You Home

Years ago, Carlos Cervantes and Roby So were arrested for their involvement in separate, unsuccessful drive-by shootings. While serving time in San Quentin, they became close friends and made a pact. When they left prison, they wouldn’t return to a life of crime like so many other inmates. They would learn how to navigate the free world, get housing and proper ID cards, and find support groups and educational programs. They’d be prepared for their return to civilization.

Carlos and Roby helped each other stick to their plan after they were paroled. But they also wanted to become shepherds, helping other paroled convicts who didn’t know how to survive outside prison. They were especially concerned about guys locked up in the 1990s under California’s Three Strikes law, men who were suddenly tossed into a 21st-century world of iPhones, transit cards, and Facebook.

“Three-strikers” are often given just 24 hours’ notice when they’re released early. With just $200 in their pocket, a 48-hour deadline to meet their parole officer, and no practical instructions whatsoever, they’re shoved out the door. Fortunately, that’s where Carlos and Roby come in. Since February 2014, they’ve been meeting newly released prisoners, driving them to a housing center, and giving them life tips along the way.

According to The New York Times Magazine, a typical ride home starts with breakfast at Denny’s or IHOP where the prisoner orders off a menu for the first time in years. Over pancakes and eggs, Roby and Carlos explain how to use a cell phone and register for welfare. Next, they stop by the nearest Target and help the ex-con buy necessary items like clothes, soap, and toothbrushes, all while coaching him through the crowded store and explaining how to operate a credit card reader.

As the trio heads to the housing center, Carlos and Roby lecture their new friend about social media and how to use government programs to further their education. They end the day with a trip to Starbucks, a big improvement over prison coffee. While most of us take all these little details for granted, it’s vitally important info if you want to be a productive member of society.

That’s why Roby and Carlos are modern-day superheroes. By guiding ex-cons through their first day of freedom, they’re giving them just enough encouragement to change their lives for good.



4Christopher Scott
The Exoneree Detective Agency

In 1997, Christopher Scott was hauled into a Dallas police station and accused of capital murder. According to the cops, Scott and his friend Claude Simmons had robbed a local home and executed the man living there. But there wasn’t any DNA evidence, and the police never found a weapon. In fact, their whole case was based on the eyewitness testimony of the victim’s wife, who initially failed to pick Scott out of the lineup.

Nevertheless, both Scott and Simmons were carted off to prison. It wasn’t until a dedicated group of lawyers and law students started digging that anyone discovered the truth: The real killer was locked up for a different crime. When the murderer confessed, both Scott and Simmons were released after losing nearly 13 years of their lives. Sure, they were compensated with $160,000 per year, but Scott wasn’t content to take the money and shut up. Wondering how many other innocent men were wrongly imprisoned, he sprang into action.

Dedicating his life to chasing down the truth, Scott founded the House of Renewed Hope, a detective agency made up of exonerees (men cleared of crimes they didn’t commit). Working out of Scott’s house, these dapper detectives, who sport fedoras and leather shoes, investigate the truly desperate cases. They tackle murders and rapes where there isn’t any DNA evidence or where racial prejudice played a role in convicting someone.

Scott and his team are incredibly skilled at convincing the actual crooks to confess their misdeeds, and they’re pretty handy at talking witnesses into renouncing questionable testimonies. The exoneree detectives are so good that they’ve received pleas for help from countries like China and Brazil.

In addition to all that sleuthing, they’ve also testified at the Texas State Capitol, lobbying for laws to prevent future miscarriages of justice. “It’s my duty to help those guys that can’t help themselves,” Scott said in an interview with The Texas Observer. So if you ever find yourself stuck with a sentence you don’t deserve, you know whom to call.

3Stephen Donaldson
Hooking Up: Protective Pairing For Punks

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Photo credit: Jimi 45

When Stephen Donaldson attended a demonstration outside the White House in 1973, he didn’t know that day would change his life. Arrested for protesting the Vietnam War, first-time offender Donaldson was locked up with a group of brutal thugs who raped him repeatedly over two days.

Over the next few years, Donaldson fell into a life of drugs and wound up back in prison on two separate occasions. Tragically, he was raped both times. But instead of succumbing to the horrors of prison life, Donaldson decided to fight back peacefully.

In the 1980s, he began counseling victims of prison rape and giving lectures on sexual assault at institutions like the NYU School of Law and the Massachusetts legislature. He even testified on a rape case that made its way to the Supreme Court. Eventually, he became president of the human rights organization Stop Prisoner Rape.

However, Donaldson’s strangest contribution to the war on prison rape was a pamphlet entitled Hooking Up: Protective Pairing for Punks. It’s a manual that instructs a straight convict to find a protector by offering himself sexually to a bigger, stronger prisoner.

The pamphlet is full of practical tips on how a “punk” can find a “jocker” to watch out for him. For example, Donaldson writes, “Spend as much time as you can with the jockers who want to hook up with you; ask them lots of questions and judge for yourself how sincere they are.” He suggests that “catchers” write up contracts with their “pitchers” to lay some ground rules. Donaldson also warns that your “daddy” might loan you out to curry favor with other inmates.

The pamphlet explains how punks will have to do a lot of chores around the cell and cautions that jockers might demand that their punks adopt a feminine name and characteristics. However, Donaldson says it’s ultimately worth it because jockers must protect their punks from rapists or they’ll lose respect among their peers. Hooking up with just one guy also reduces the chances of contracting AIDs, which is unfortunately what happened to Donaldson.

The activist passed away in 1996.

2James Scott
The Big House Boxer

In 1978, Eddie “The Flame” Gregory was the No. 1–ranked light heavyweight, a boxer with a stellar record of 29–3–1. No one took it seriously when washed-up bruiser James Scott challenged him to a fight. But Scott’s promoters were offering $15,000, and HBO was airing the match. So Gregory accepted.

Scott wasn’t some punch-drunk bum. This guy had the eye of the tiger. Unlike Gregory, Scott was an inmate at New Jersey’s Rahway State Prison who believed he might earn his release if he won the light heavyweight belt.

Although Scott had spent most of his teenage years in detention centers, he had trained as a boxer. When the 18-year-old was sent to Trenton State Prison, he learned the finer points of pugilism from an older inmate. Scott even sparred with the famous Rubin “Hurricane” Carter.

Over the next few years, Scott was in and out of prison. On the inside, he became the New Jersey prison champ. After his 1974 release, he transformed himself into a successful professional with his eye on the title. When Scott was tossed into the clink again for robbery, his generous, publicity-savvy warden promised to help Scott earn his freedom if he could restart his career.

So while he trained, Scott contacted some of boxing’s top promoters, setting up a series of light heavyweight matches, all staged inside Rahway Prison. Each time, Scott made short work of his opponents, fighting his way toward the No. 1 contender, Eddie Gregory.

Even though Gregory was the favorite, Scott destroyed him in a 12-round beatdown on HBO. Suddenly, Scott was a media darling. In November 1978, the World Boxing Association (WBA) declared that he was one of the best boxers on the planet. Unfortunately, Rahway’s friendly warden was replaced with a man who hated Scott. When the boxer asked a judge to set him free, the court turned him down.

Later, the WBA decided they didn’t want an inmate for a champion and removed him from the rankings. Heartbroken, Scott watched his career take a nosedive. He was finally released from prison in 2005. Although his last two fights were losses, he retired with a career of 19–2–1 and was inducted into the New Jersey Boxing Hall of Fame in 2012. As of 2015, Scott lives in a nursing home and is battling dementia, his toughest opponent to date.

1T-Bone
The Prison Vigilante

There’s one man in the Arizona correctional system who thinks it’s his duty to stop sexual assault in prison with his bare knuckles. They call him “T-Bone,” and he’s a one-man army who specializes in beating prison rapists to a pulp.

Standing 196 centimeters (6’5″), this former Marine fell into a life of crime after leaving the military. After a brief stint as a bodyguard, he ended up in the cocaine business, got high on his own supply, and soon found himself incarcerated. He was also accused of kidnapping and robbery, but in January 2015, he was cleared of all major charges.

Unfortunately for T-Bone, he was sentenced to 13 years behind bars for a lesser charge, which is good news for anyone who needs protection. A devout Christian, T-Bone believes it’s his divine duty to guard weaker prisoners. He discovered his calling in 1986 after learning that an 18-year-old had been gang-raped by a group of thugs. Inspired to take a stand, T-Bone declared war on all prison perverts, a war that’s involved a lot of bloodshed.

In his battle against rapists, T-Bone has faced guys carrying infected hypodermic needles and razors. Once, somebody whacked him in the head with a sock full of rocks, and he’s been shanked at least once. Angry rapists have put bounties on his head. Once, he was jumped by a gang and nearly raped himself. But he was saved by a few friendly inmates.

Despite the danger, T-Bone never backs down. Whenever some sicko corners a weaker inmate, T-Bone shows up with fists flying. In an interview with Vice, T-Bone explained how he keeps going. “My belief in God gives me the divine power to do all things through His Spirit,” he said.

As of late 2015, T-Bone is located in a supermax prison, but he’s still ready to pound any would-be rapist into the pavement. But T-Bone knows that violence isn’t the ultimate answer to the problem of rape. According to T-Bone in his Vice interview, the only real solution is letting God into the prison system “because God is love, and where there’s love, there’s peace.”

Nolan Moore is a writer who hails from Texas. If you want, you can friend/follow him on Facebook, or you can send him an email.