His manner of spitting out the red pill was the dumbest thing ever. Once he betrays the free humans he is of no value to the machine and they have no reason to accept him back into the matrix in any capacity, let alone fulfill his wealth/power fantasies.
Yeah, it's like every other movie where a character engages in negotiation with a murderous psychopathic villain, the chump thinks he's in control right up until Hans Gruber shoots him in the head.
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