Red Dillard was a Harlem-based crime boss who was dubbed “The Most Dangerous Man in the Country.” Born Dillard Morrison in Alabama, he was noted for being an aggressive child, regularly getting into fights with neighborhood bullies. He gained the name “Red” after a botched hair straightening attempt. His criminal career would start sometime after moving to New York City in 1937 at the age of 17 or 18.
Rising Through the Ranks
Red Dillard quickly took to hustling and street work to provide for his family. He paid close attention to which bosses ran the gambling rackets, who was in charge of prostitution, who ruled drugs and extortion and mixed with those in the different circles. Dillard was considered a hard worker and someone who could be trusted to carry out tasks.
He was also seen as having leadership ability and drawing others to him. In the late 1930s, several bosses took notice and he began to get regular work. His toughness was also valued and he would work in the extortion and robbery rackets at this time.
Working Under “Big” Joe Richardson
A man with fingers in different pots, Big Joe had a rogues gallery of lieutenants over his rackets. These leaders ran small rings of criminals picked by the boss himself. By 1940, Red Dillard–who had worked in Big Joe’s operation for a while–was promoted to being an underboss of sorts.
He would evade arrest for some time because he was so aggressive and hyper-violent that he intimidated victims–often after pummeling them. It would be years until law enforcement actually found something that would stick to Red Dillard and lock him away for a significant amount of time.
Before reaching 30, “Red” Dillard Morrison would progress through Harlem’s underworld at a rapid pace and start his own operation. In the next segment, we’ll explore his operation and eventual decline.