The legend describes Billopp's alleged role in securing
Staten Island for New York. To settle a territorial dispute between New York and New Jersey, the
Duke of York was said to have come up with a novel solution: he declared that all islands in New York Harbor that could be circumnavigated in 24 hours would belong to New York, and if such a voyage took longer than that, they would belong to New Jersey. Although there have been many descriptions of what happened during the period of before and after Billopp circumnavigated Staten Island, one, which is described in the following text, has been the most reiterated: At this time, Billopp was just across the waterway from Staten Island at
Perth Amboy, New Jersey aboard a small two-gun vessel called the
Bentley. Billopp was selected for the duke's challenge. While struggling to figure out how to complete the more than voyage within the duke's time frame of 24 hours, Billopp reasoned that if he packed the deck of his ship with empty barrels, the extra surface area could harness some more wind giving his ship a slight boost in speed. Thus equipped, Billopp completed the circumnavigation in just over 23 hours and secured Staten Island for New York. In recognition of his achievement, the duke awarded Billopp a total of of land located in what is now the Tottenville section of Staten Island. On this land, Billopp built his house, which he named the Manor of Bentley in honor of his ship. While this anecdote has been widely repeated, including by
Mayor of New York City Michael Bloomberg, reliable historical documentation of the event is sparse. In 2007,
The New York Times addressed the issue in a news article, which concluded that this event was heavily embellished over the years and almost certainly originated in local folklore.
YouTuber CGP Grey provided a similar conclusion in a 2019 video addressing the story of the Staten Island race and its historical discrepancies. ==Naval career==