castle williams

He Swam from Castle Williams to the Battery

William R. Webb
Sen. William R. Webb

When I was researching the book, I came up with way more information than I could ever use. A lot of what I found were tall tales and historical stories that popped up. One was about Captain Billy Web, and it seems like this is the best venue to tell his story. If you’ve ever stood on the shore on Governors Island, think about jumping into the water and swimming towards Manhattan.

In the almost 100 years that Castle Williams served as military prison, many attempted to swim to freedom. Most drowned in their attempt, but not Captain William Robert Webb, of the 2nd North Carolina Cavalry. As the tale goes, he successfully navigated the notoriously treacherous tides, eddies and currents and swam away from Governors Island to the Battery. In some accounts, he only had the use of one arm, due to injuries. Wearing his gray Confederate States of America officer’s uniform, Captain Webb splashed ashore and introduced himself to several passersby, and truthfully explained that he’d just swum from the island. The New Yorkers he met were amused—and nobody turned him in. He took a train home to the South. Webb got married and had eight children and founded what is today The Webb School in Bell Buckle, Tennessee. In 1912, voters in Tennessee elected him to Congress.

Webb died in 1926 at age 84.

Kevin C. Fitzpatrick has written and edited seven books with ties to New York history, including "The Governors Island Explorer's Guide" and "World War I New York: A Guide to the City’s Enduring Ties to the Great War." Kevin is a licensed sightseeing guide and has been leading walking tours since 1999. He resides in Manhattan.