[WATCH] How New Jersey Lost Staten Island to New York

The video investigates the popular legend of how New Jersey lost Staten Island to New York in a sailing race. According to the tale, Captain Christopher Billopp of New York supposedly won Staten Island by circling it in under 24 hours in his ship, the Bentley, aided by empty barrels to catch the wind. However, a deep dive into historical records, including articles from The New York Times and various historical books, reveals inconsistencies in dates, details of the race, and even the identity of Captain Billopp. The narrator traces the story's origin to Reverend Gabriel Poillon Disosway, a local chronicler, who likely shared it as an embellished oral history in the mid-1800s. The investigation, which included visiting the New York Public Library and the Conference House (also known as Billopp Manor) on Staten Island, ultimately reveals the Staten Island race story to be a charming but historically unsubstantiated "tall tale" that evolved over centuries.