Spoiler Warning: Plot and/or ending details are in the text which follows.
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- "We are about to put the Darwinism back in Social Darwinism, and brother, it is gonna be fun."
- ― Lester Crest
Lester was involved with a heist team operating out of North Yankton in the early 2000's. However, even after Lester's pleadings for them not to continue with the job, the crew went along with it anyway. The heist was a failure as a result, and the crew were either killed or arrested by the FIB. Lester went into hiding immediately afterwards, covering his tracks and cutting off all contact with any criminal connections made in the state. At an unknown time, Lester moved to Los Santos, San Andreas.
Lester met Gary Mitnick in 2009, otherwise known by his online persona, eHero. The two would partake in various criminal operations and "pwnings" which Lester himself was very fond of. Gary would often object to Lester's obsession with sorority girls, as Lester would lie about his age and attempt to get close to them. He would be ousted numerous times during this period, as one girl asks on LifeInvader, "are you really 16?". Whether or not Lester is indeed a paedophile is speculated upon wildly by Gary and later, Niko throughout the events of San Andreas Connection.
In 2014, Lester is the one responsible for blackmailing Niko Bellic and forcing him out of hiding in San Andreas Connection. Arranging to meet at Lester's Warehouse, the two form a complicated bond and Niko eventually gives in to Lester's demands.
Lester is cautious with how he tackles a heist opportunity, but is nevertheless enthusiastic when a heist is successful. Despite this, Lester has managed to remain anonymous, from the FIB and oddly, the IAA.
Lester is often cocky when it comes to pure dialogue, never passing the opportunity to add snark to a conversation. He is even noted calling Gary Mitnick, "Mitdick", "Dick", "Chump", and even, "Plastic Pusher". However, Lester acknowledges the appropriate situations when to stay focused, such as during heists.
While he respects Niko Bellic, Lester will go out of his way to draw out jokes and punchlines that anger Niko during the course of San Andreas Connection. This means Lester may have a personal bias towards people originating in the Yugoslavia region of Europe.