Jimmy McCullough learned the carousel business from his father, James McCullough, who began his career working on the Steeplechase and Stubbman carousels. Working in Coney Island is a family business going back generations for Jimmy who is a descendent of both the Tilyou and the Stubbman families. He has worked on a total of four carousels in Coney Island including the B&B Carousell, which he bought from his cousin. Later he worked in partnership with his daughters to operate traveling rides starting with the SkyWheel in Toronto.
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