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.