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For other uses of the same name, see Lester. Lester was born with a wasting disease that has destroyed his muscle strength to the point where he has to manoeuvre in a wheelchair, though he can still walk short distances with the help of a cane.

Sometime after he finished his studies, Lester applied for a faculty position at the University of San Andreas, Los Santos , but was not accepted. As an act of revenge, he hacked their systems, a fact that Lester claims "never gets old". At an unknown point in time, Lester moved out to the Midwest, where he met and became affiliated with bank robbers Michael Townley and Trevor Philips , and became a regular member of their heist crews since the start of their partnership, working mostly as a planner and information scout.

During this time, Lester likely told both of them about the Union Depository , a superbank in Los Santos where the government keeps their gold reserve, leading to the three of them to come up with potential schemes on how to rob the place. In , Lester refused to participate in robbing a cash storage facility in Ludendorff , North Yankton , believing it was a bad idea. His suspicions are later confirmed when he discovers that, during this same heist, Michael was apparently gunned down and another associate, Brad , was subsequently arrested.

Following the botched heist, Lester moved to Los Santos and purchased a garment factory in La Mesa , along with several other properties to use as fronts for his various operations. During this time, Lester investigated the Ludendorff heist and learned that Michael was alive but had faked his death and moved to Los Santos as well, having previously made a deal with FIB agent Dave Norton.