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During a meeting with George, Yankee owner George Steinbrenner becomes quite taken with his lunch from a delicatessen near the stadium. Faced with Steinbrenner's growing obsession with a daily calzone, George is more than happy to oblige and bring him one, especially since it puts him in his boss' good graces. But when a misunderstanding over a tip leads George to being banned from Paisano's deli, he's forced to find another way to get it. Meanwhile, as Kramer develops his own obsession with freshly dried laundry, Jerry dates Nicki, a woman whose stunning beauty persuades anyone to do as she says.
After learning of their suspicious bet, Jerry warns Elaine she's being set up to go out on a date with by her friend Todd Gack. Todd's subsequent offer to get Jerry some prized Cuban cigars only increases Jerry's suspicions that he's using it to see Elaine again without having to actually ask her out. And though he vehemently denies using the lost bet or the cigars as a cover, Elaine begins to wonder after discovering they are meeting Todd's parents for dinner. Meanwhile, as Kramer discovers that the expensive cigars Todd sold Jerry are actually from Peru, George enlists Newman to buy Steinbrenner's lunch.
When Newman calls in sick on a rainy day, George must find someone else for the calzone run at Paisano's. Agreeing to carry out the mission for his friend, Kramer also persuades the deli's owner to let him heat up his clothes in his oven. But when Kramer isn't allowed to pay for the lunch order in pennies, George is left to explain to an irritable Steinbrenner. Finally, after Nicki also falls prey to Todd's stealthy dating ploy, Jerry gets revenge by paying for the cigars with $300 ... in pennies!