The "Pilot's Monument" of harbor pilot Thomas Freeborn(1808-1846), ca. 1865.

Thomas Freeborn was navigating the ship John Minturn into New York Harbor amid a raging storm. Despite his best efforts, the ship ran aground and Freeborn and many others perished. Initially interred at the Rutgers Street Burial Ground in New York City, he was reinterred at Green-Wood by his fellow pilots, who erected the "Pilot's Monument" in his honor.

The marble monument features imagery associated with harbor pilots. Atop the base is a ship's capstan, with anchor cable coiled around it, and rising above is a mast whose truncated top symbolizes a life cut short. Atop the mast stands a personification of Hope, holding an anchor at her side. An image of the John Minturn, struggling in the waves, appears on the base. The monument was placed on this hill so that it could be seen by pilot’s working in the harbor waters below.

(Lot 1221, Sec. 111)