"Where is the Difference" - Puck cartoon satire, 1894

The Outlaws Who Built NYC

Scandal. Subterfuge. Street-level rebellion. The real architects of New York City weren’t saints. They were schemers.

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.

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. Literally.

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.

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.

Main Features:

  • 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

Meeting point: Millennium Downtown New York, 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

Mapped meeting point for The Outlaws Who Built NYC at 55 Church Street, Manhatttan

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

“The Outlaws Who Built NYC is superb as all the others have been. Beautifully structured, thoroughly researched, delivered with clarity and enthusiasm, and enlightening from start to finish. And fun, even. If you compared the Purefinder tours to other New York walking tours, you would say they are by far the best. But you can't compare them. They are literally incomparable. Well-chosen slices of the always interesting New York story, and fascinating looks at the often-unknown people that make the story, vividly brought to life.”

notpracticing (TripAdvisor) 5*