|“||Men aren't built for monogamy... because of evolution. We're -- we're -- we're programmed, you know, to --to spread our seed.||”|
— Lester to Dean
Lester's wife Mindy cheated on him by having a sexual relationship with someone in a bowling league. Distressed, Lester goes to drink in a bar where he is encountered by Sam, who offers him a way to solve his problem.
Sam takes Lester to a crossroads and has him summon a crossroads demon into a Devil's Trap, but before Sam can intervene, Lester tells the demon Dar, that he wants his wife killed in retaliation.
The demon Crowley gives Dean Winchester the task of killing Mindy, as a way of satisfying the Mark and fulfilling a task. Dean reluctantly agrees, somewhat, and goes to the house only to notice Lester parked outside. Dean enters the car, revealing his status as the demon hitman and asks why Lester is still here.
Lester tells him that he wants to make sure everything goes right. Tearfully he adds that his wife ruined him by cheating and wanting a divorce. Dean however, doesn't buy what Lester is saying and claims to know that Lester had been cheating on his wife first. Lester shamelessly admits to his infidelity and tries to excuse it. After Dean hits Lester and calls him a loser, Lester demands Dean to finish the job.
Not taking kindly to Lester's demand, Dean stabs him with the First Blade, killing him and voiding the crossroads contract, thus denying Crowley Lester's soul.
- Season 10
- Though he sold his soul to a demon, Dean killing him before the deal was sealed means that Lester's soul would have been spared from Hell. This makes Lester one of the few people to not go to Hell under terms of a deal.
- However, given Lester's selfish nature, he might be sentenced to Hell anyway.