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Working alongside his friend Dino Zerilli he began small by selling ecstasy and molly to college kids and they made a good amount of money out of that.
They often hung out at the Ooh Fa pizza restaurant which brought them into contact with Christopher Moltisanti.
The young, would-be stick-up men got high on "crank" (Crystal meth) and Jackie almost decided not to go through with it.
Jackie planned the robbery of a Jewel concert at Rutgers and drove the getaway car for Christopher and Benny Fazio. Jackie was subsequently dumped by Meadow after she found him cheating on her with a hooker.However, with the rank and file of the Di Meo Family baying for Jackie's blood, Tony refused to intervene.