The next scheme takes viewers from the sun-bleached streets of Central New Mexico to the cold, snow-covered alleyways of Cicero, Illinois. Before Jimmy was a lawyer, he was Slippin’ Jimmy, a legendary conman who made his beer money tricking the populous of the Chicago suburb into parting ways with their hard-earned cash. In Season 1, there are several looks at some of the rackets that Jimmy runs with his close friend Marco (Mel Rodriguez) in the dive bars of Cook County, but the best one of these by far is the fake Rolex scam.
All that is needed to pull off this scam is a well-dressed accomplice, a couple hundred in cash, a fake Rolex, and a charming con man to run the game. Jimmy approaches the mark in a bar, and when the bar closes, tells the unwitting fellow about a cool after-hours spot nearby that’s open all night. On the way to this imaginary spot, they happen across a wallet on the ground, with a couple hundred in cash, fallen from the pocket of the inebriated businessman passed out nearby.
But there’s more money to be made than just the wallet. Glinting on Marco’s wrist is an expensive watch, which Jimmy tries to keep for himself, disguising the watch’s true value. When the mark insists on keeping the watch, Jimmy protests, leading the poor unfortunate man to offer Jimmy all the cash in his wallet for a worthless replica. The mark runs off into the night, unaware he’s just been taken for a ride, leaving Jimmy and Marco to split the cash.
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