Red Dillard worked under “Big” Joe Richardson for a few years and handled extortion and protection of his rackets. By the end of the 1930s, he had his mind on establishing his own foothold in Harlem having seen how Big Joe ran his operation and having knowledge of areas he could set up camp.
His Own Boss
During World War II, Dillard left Big Joe’s operation and would enter the drug trade. He struck up a working agreement with Lucky Luciano, the boss of the powerful Genovese crime family. He would receive heroin from the Genovese and delegate the distribution to his runners who sold it outside of Harlem. Bolstering his drug business was a prostitution racket.
Red Dillard would become a known name outside of Harlem’s crime circles thanks to his donations to different causes for Black people. This combination of being a philanthropist and intimidating force meant that people would either look out for Dillard and give him a heads up on police activity or say nothing if they were a victim.
Federal law enforcement went to great lengths to capture Red Dillard. They finally got it right due to a long game of putting an undercover agent in the Harlem drug scene. This agent eventually worked his way through Dillard’s operation. With the evidence and an opening, he was busted in May 1950 on possession and sale of heroin.
It was noted that Dillard and partner Robert “Gator” Lee supplied Boston and Chicago with the bulk of the heroin on the streets. Dillard was given five years in prison. In 1953, he was injured in a prison melee that resulted in both legs being paralyzed.
Upon leaving prison in 1955, he vowed to leave crime. He shunned gifts from mob bosses for not providing evidence on his partners during his sentence. Since Dillard still had money from his active days, his intent was to get into real estate or services. It was the death of his wife at the age of 33 in a medical accident that drove him back to violent crime.
Dillard took to cocaine and fighting during 1964. A sting would see him back in prison once more for a ten-year stint. He opted to move out west to Los Angeles where he dove back into the drug trade.
Five years later in 1979, Red Dillard went to jail one last time after a girlfriend turned him over to federal law enforcement. He would lose his battle to bladder cancer behind bars in 1989, at 69 or 70 years old.