History Daily 1259: Boss Tweed Escapes Prison
5 snips
Dec 4, 2025 Dive into the audacious escape of Boss Tweed, the infamous New York politician, who cunningly eludes his guards during a home visit in 1875. Explore how his corrupt influence was unveiled through investigative journalism, leading to his monumental conviction. The story takes a thrilling turn as Tweed orchestrates an escape plan, fleeing to New Jersey and beyond, only to be eventually recognized and captured abroad. It's a captivating tale of power, corruption, and the relentless pursuit of justice.
AI Snips
Chapters
Transcript
Episode notes
Daring Midnight Wagon Escape
- William "Boss" Tweed slipped away from his guards during a supervised home visit and hid in a covered wagon to escape Ludlow Prison.
- He crossed the Hudson by rowboat and began a fugitive life hiding in farmhouses and on beaches after December 4, 1875.
How Political Machines Consolidated Power
- Boss Tweed built power by controlling nominations, rigging votes, and steering public money to allies.
- That machine made him hugely wealthy and untouchable in many civic circles until the investigation broke it open.
The Paper That Took On Boss Tweed
- British-born editor Louis John Jennings persisted when others feared Boss Tweed and used the New York Times to publish exposés.
- A whistleblower, former sheriff Jimmy O'Brien, delivered three years of secret city accounts that became the smoking gun in 1871.