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By the age of 12, Lester had fallen in with the Halstead Street Boys, a gang that ruled the streets through intimidation and violence. His early offenses included theft and ultimately gun violence, leading to his first serious arrest at 13 for shooting a fellow gang member. Sent to a harsh reformatory for what was supposed to be rehabilitation, Lester instead emerged more hardened and resolute in his criminal pursuits, leading to a string of arrests in his teenage years.
His time in juvenile detention did not deter him; by his release, he had only become better equipped for a life of crime, transitioning from petty theft to serious robberies, earning a notorious reputation in the business.