Sweet Spot With Mike Sugerman: Eat Your Way Through NYC's Mob History On Airbnb's Most Popular Tour


NEW YORK (WCBS 880) -- Organized crime on the Lower East Side? There's no one better to hear the stories from than Dennis O'Leary.

"I grew up with it and then fought against it and now I'm talking about it," said O'Leary, who grew up in an apartment building where he claims his neighbors, his friends' dads and then his buddies got involved in the "family business." "The guys I grew up with had like 200, 300 kills."

O'Leary spent eight years on the streets in the NYPD's Organized Crime and Narcotics units. The now-retired police officer gives tours of the streets he knows from both sides with history and food thrown in.

"I like to start off by showing you guys my police ID, it's always nice so you know I'm legit," O'Leary told Mike Sugerman in this week's Sweet Spot. "We start here at John's on 12th Street, it's where the mob was founded. In 1931, when they decided who's going to run which group and become these named families. That actually happened here in John's."

Some of what he talks about you can read on the internet, but other spots are more personal.

"I'd be out there buying drugs, good quantity of cocaine and I just got rushed from the back, thrown on the floor and they basically ruined work we were working on for like a year," O'Leary said."I also knew someone from the neighborhood growing up they believed he was a rat and when they found his body he had a dead canary in his mouth."

All this history comes with a side of meatballs, pizza, cheese and cannoli. It's all part of an Airbnb tour and the company tells him it's the most popular one in the world.

"I think it's both the kind of over-the-top drama of the stories but also that you understand the motivations. There's a lot of family aspects," said tourist Lawrence Newport.

'We've walked all over the city, seen all sorts of different sides of things and then you do a tour like this and you realize how much you've missed," said tourist Ella Kahn.

O'Leary has moved on. He's now in technology and donates the money he makes on the tours to charity as a way to give back. 

"I'm going to hell regardless of what I do but maybe one level of hell above the lowest level," O'Leary said.