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In John Wick 1, an assassin named Perkins decided to take Viggo's contract to kill John at the Continental. As we learned early on, the repercussions of violating the Continental rules are extremely severe, leading to death.

What I don't understand then is why Perkins would not only believe $4 million would be enough to save herself. As Winston says at the end of Chapter 2, he notes that "John's life is now forfeit". So as any reasonable assassin would, just as Cassian and John respect the rules of the Continental, why would Perkins both take the contract and meet Winston? Was she just an amateur at her job?

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Clealy $4million dollars was enough of a temptation to take the risk.

She's clearly not an amateur...just greedy! You can run fast and far on $4m.

She's described as "brazen" (which is defined as "bold and without shame.") and has little respect for rules.

How brazen. If they're willing to break the rules of Continental, double the bounty.

During the fight with Wick she demonstrates this..

WICK: I never knew Ms. Perkins to get out of bed for less than three.

PERKINS: Viggo's giving me four to break hotel rules.

WICK: That's unwise, assure you.

PERKINS: You were always a pussy.

Indeed, when being held by Eddie (the assassin in the room next door to Wick) she shows disrespect for Continental management.

EDDIE: You've broken the rules. You've done business on Continental grounds. And management does not take kindly to that sort of behavior.

PERKINS: Fuck management.

All of this is evidence of willingness to take risks.

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