The streets have always had a simple rule. You either go to prison or you go to the grave. Almost every kingpin in American history has ended up in one of those two places. But a small number of them made millions and never spent a day behind bars for it. Some walked away. Some vanished. Some retired. Some are still alive today. This is their story, from number ten to number one.
At number ten is Alberta Green, the policy queen of South Jamaica, Queens, in the 1930s. Most people have never heard of her, and that is exactly how she wanted it. Green ran a numbers bank that generated thousands of dollars a day, at a time when most black families were surviving the Great Depression on pennies. She employed between five and ten collectors and several runners. She was arrested once, in 1935. After that, she disappeared from the public record entirely. No trial, no conviction, no prison sentence. She simply faded out of the headlines and into quiet wealth. In a world where nearly every male numbers operator in New York eventually went to prison or was killed, Alberta Green walked away clean.
At number nine is Casper Holstein, who did not just run the numbers racket in Harlem. He invented the modern version of the game. Born in the Virgin Islands, Holstein came to New York as a teenager. He figured out that if the winning number was tied to the last three digits of the New York Clearing House's daily financial totals, nobody could fix the results. That single idea turned the numbers game from a small-time hustle into a multi-million dollar industry. At his peak, Holstein was making $12,000 a day in the 1920s. He owned nightclubs, funded scholarships for black students through Opportunity Magazine, and donated money to build Harlem's first Elks Lodge. In 1928, white mobsters kidnapped him and held him for a $50,000 ransom. He was released after three days. Instead of going to war, Holstein started pulling back. By the time Dutch Schultz moved to take over Harlem's numbers in the early 1930s, Holstein was already gone. He died in 1944, a free man.
At number eight is Stephanie St. Clair, known as Madame Queen. She arrived in Harlem from the French West Indies with almost nothing. Within a few years, she had built one of the most profitable numbers operations in the city, employing over 50 runners. She took out ads in the Amsterdam News, Harlem's biggest black newspaper, to publicly attack corrupt police officers by name. When Dutch Schultz tried to take over her territory, she did not fold. She hired Bumpy Johnson as her enforcer and waged a war that killed over 40 people. When Schultz was gunned down in a Newark restaurant in 1935, St. Clair sent a telegram to his deathbed. The message was simple: "As you sow, so shall you reap." She served eight months in a work camp for possession of policy slips, and that was it. She retired in the late 1930s and moved to a mansion on Long Island. She died in 1969 at approximately 72 years old.
At number seven is Edward Jones, who built a $25 million policy gambling empire on Chicago's South Side. The Jones brothers, Edward, George, and McKissack, ran the largest policy operation in Chicago, employing hundreds of runners across Bronzeville. They invested their profits into legitimate businesses, funded community organizations, and donated to the NAACP. Then the Italian mob came calling. In 1946, Sam Giancana and the Chicago Outfit kidnapped Edward Jones and demanded $250,000 and the keys to his entire policy operation. Teddy Roe negotiated the ransom on behalf of the Jones family. The money was paid and Jones was released. Then Edward Jones did the smartest thing any kingpin on this list has ever done. He took his entire family and moved to Mexico. He did not try to fight the mob or rebuild. He took his millions and left the country. He died free, never convicted and never imprisoned. His granddaughter made a documentary about his life in 2022, because even his own family did not fully know the story until decades later.
At number six is Teddy Roe, who took over Chicago's black policy racket after Edward Jones fled to Mexico. Unlike Jones, Roe refused to give an inch to the Italian mob. Sam Giancana wanted his operation, and Roe said no. They tried to bomb his house and he survived. They sent men to kill him and he survived. For years, Teddy Roe was the only black man in Chicago openly defying the Italian Mafia. On August 4th, 1952, Roe was ambushed outside his home. Two men with shotguns caught him getting into his car, and he was killed on the spot. But the law never got Teddy Roe. He was never convicted, never indicted, and never spent a single day in prison. He died from a rival's bullet, not from a judge's sentence.
At number five is Pee Wee Kirkland, one of the most talented basketball players ever to come out of New York City. Richard Kirkland was recruited by two different NBA franchises and turned them both down. The streets paid better. By his early 20s, he was making millions in Harlem's heroin trade while dominating the legendary Rucker Park basketball tournaments during the day. He was a folk hero, the man who could have gone pro but chose the game instead. But Pee Wee did something almost nobody in his position has ever done. He walked away. He transitioned out of the drug trade, was never convicted on drug charges, and never served a prison sentence for trafficking. He became a youth basketball coach in New York City, using the same courts where he once recruited to now keep children away from the life he left behind. Pee Wee Kirkland is alive today and has been free his entire adult life.
At number four is AZ Faison, one of three kings who ran Harlem's crack trade in the 1980s. Rich Porter, Alpo Martinez, and AZ Faison became the subject of the 2002 movie Paid in Full. By 21, AZ was making over $10 million a year and was one of the biggest distributors in the entire state of New York. Then his partners started dying. Rich Porter was murdered by Alpo in January 1990, and Rich's 12-year-old brother Donald was kidnapped and killed. Alpo was arrested, confessed to 14 murders, and entered witness protection. In 2021, Alpo was shot and killed on Halloween morning in Harlem. Azie Faison is the only one who survived. He quit the game, produced a documentary called Game Over, wrote a book, and became an anti-drug activist. He was never convicted of drug charges and never spent a day in prison for trafficking. Two out of three kings are dead. The third is alive, free, and telling the story.
At number three is Red Top Walter, who was 16 years old when she became one of the biggest dealers in Harlem. A girl running a multi-million dollar operation in a world run by grown men. At her peak, Red Top was moving $300,000 a month. She ran her operation from the same blocks where Nicky Barnes' council operated. She was known for her red hair, hence the name, and for the respect she commanded from dealers twice her age. She was never arrested and never spent a day in jail. The law never caught her, but the streets did. At 16, Red Top was accidentally shot and killed by one of Nicky Barnes' bodyguards. Sammy Davis Jr. attended her funeral. She made this list because the law never touched her, but she never got the chance to spend what she earned.
At number two is George Edward Wright, whose story stretches from New Jersey to Portugal. In 1962, 19-year-old Wright robbed a gas station in New Jersey and killed the attendant over $70. He was sentenced to 15 to 30 years. In 1970, he escaped from Bayside State Prison, stealing the warden's car on his way out. On July 31st, 1972, Wright boarded Delta Flight 841 from Detroit to Miami disguised as a priest under the alias Reverend Larry Burgess. He had a gun hidden inside a hollowed-out Bible and demanded $1 million in ransom. The FBI delivered the cash, with an agent walking onto the tarmac in swim trunks to prove he was not armed. Wright released the passengers, forced the crew to fly to Algeria, and disappeared. He obtained a Portuguese identity, married a Portuguese woman, and had two children, living in a quiet beach town near Lisbon for nearly four decades. In 2011, the FBI found him through his sister's phone records. He was arrested at age 68 and admitted his identity. Portugal refused to extradite him because he was a citizen and the statute of limitations had expired. He was released. George Edward Wright is alive and free today. His hijacking led to the creation of modern airport security.
At number one is Frank Matthews of Brooklyn, New York. On July 2nd, 1973, Matthews was supposed to appear in a Brooklyn courthouse. He was facing 50 years on six counts of tax evasion and conspiracy to distribute heroin and cocaine. He never showed up. He took $20 million in cash, took his girlfriend Cheryl Denise Brown, and vanished from the face of the earth. Matthews had been the biggest black drug trafficker in America. His operation spanned 21 states, and he was earning $77 million a year in today's money. He organized the first national summit of black dealers and defied the Italian Mafia to their faces. He paid stewardesses $1,000 a month to smuggle product in their flight bags, and his Brooklyn drug mills were fortified with steel walls and armed guards. The FBI placed a $20,000 bounty on his head, the highest since John Dillinger. They searched every country they had access to and followed every lead. Nothing. More than 50 years later, Frank Matthews has never been found. There has been no sighting, no fingerprint, no confirmed contact with family. His girlfriend Cheryl Brown has never been found either. Nobody in his organization across 21 states has ever said a word. Every other kingpin in history has the same ending, prison or a casket. Frank Matthews wrote a third option. He picked up his money, took the one person he trusted, and disappeared so completely that the FBI eventually stopped looking. That is why he is number one. Not because he was the richest, and not because he was the most violent, but because in a game where everybody gets caught, Frank Matthews is the only one who never did.