The Outlaws Who Built NYC

Scandal. Subterfuge. Street-level rebellion.

The real architects of New York City weren’t saints. They were schemers.

Why This Tour?

If you think NYC was built by polite handshakes and zoning meetings, think again. This tour throws you straight into the alleyways of history with the outlaws, hustlers, and political schemers who actually built the bones of the city, one bribe, brawl, and backroom deal at a time.

Who You'll Meet

Forget the gangland clichés. This walking tour uncovers the radical, corrupt, and wildly enterprising figures who shaped New York City, from pirate captains and Wall Street bombers to bank fraudsters, rogue publishers, and NYPD whistleblowers. It’s a crash course in how NYC was built not just by power and politics, but by those who bent the rules, challenged authority, and sometimes blew things up.

This tour isn’t about mob bosses and speakeasies. It’s about the deeper, dirtier truths behind the institutions that still define New York City today.

Where You'll Go

We walk from colonial waterfronts to 20th-century crime scenes, tracing the hidden connections between early Muslim settlers, media martyrs, deceptive charters, and the origins of the FBI. You’ll hear about the lost ship of Adriaen Block, the scandalous career of Madame Restell, the corruption unearthed by Frank Serpico, and the high-society roots of men like Jeremiah Hamilton and Anthony Van Salee, who climbed America’s ladders on outlaw terms.

Main Stories & Scandals

Pirates & Privateers

From Captain Kidd to Adriaen Block: maritime origins of NYC’s outlaw economy

Radicals, Rebels & the Press

John Peter Zenger’s seditious libel case and the “freedom of the press” that followed

Wall Street Bombing & Federal Power

How the 1920 terror attack helped birth the modern FBI and reshape policing in NYC

Schemes & Scandals

The Manhattan Company’s water charter ruse, the Brooklyn Bridge wire fraud, and other forgotten cons

Corruption & Exposure

From the Knapp Commission to Frank Serpico: the NYPD’s long war with itself

Tour Details

Meeting point: M Social Hotel New York Downtown (formerly Millennium Downtown), 55 Church Street, New York, NY 10007 (OUTSIDE the main entrance on Church Street, NOT the Fulton Street entrance)

Endpoint: White Horse Tavern, Bridge Street, Financial District

Tour length: 2 hours

Distance covered: 1.3 miles

Meeting Point: M Social Hotel New York Downtown (formerly Millennium Downtown), OUTSIDE the main entrance on Church Street (NOT Fulton Street)