A Dollop Crossover | Ben Naddaff-Hafrey on Staten Island and the Revolutionary War
Sep 17, 2026 · 1h 20m
Summary
This episode explores the "Staten Island Problem," detailing how the borough's residents actively resisted the American Revolution to maintain lucrative trade with the British Navy. Hosts Dave Anthony and Ben Nadaf discuss the story of Colonel Christopher Billup, a loyalist who collaborated with the British, and his rivalry with rebel spy Nathaniel Fitz Randolph. The narrative covers the island's secessionist tendencies, the kidnapping of the Colonel, and the absurdity of a rebel soldier shooting a horse to avoid noise during an escape.
Topics discussed
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Intro: Malcolm Gladwell and the Dollop
Guest Introduction and Staten Island Context
Staten Island's Distinct Identity and Secession
Colonel Billup and the Island's Economy
Staten Island's Loyalist Stance in 1776
Trade with the British Navy and Rebel Tensions
British Occupation and the Colonel's Role
The Kidnapping of Rebel Scout Fitz
Prisoner Exchange and Colonel's Imprisonment
Washington's Failed Raid on Staten Island
Looting, Destruction, and British Departure
Post-War Losses and Billup's Exile
Conclusion and Book Recommendations
Promo: The American Way of Killing
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