Revisionist History: The Staten Island Problem Revisionist History: The Staten Island Problem

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

Sponsors: ChatGPT, PayPal, and US Mint 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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