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"This is the first time I've done it with the mayor of anything," said Santa, who is marking his fifth year on the job.
Reardon said he was elated to help Santa pass out the $100 bills.
"That was pretty amazing," Reardon said after handing a bill to a woman outside of a thrift store. "I've never experienced anything quite like that."
James expressed a similar sentiment.
"This is about as cool as it gets," he said. "This is the most fun I've had in a long time."