The Bowery Boys: New York City History

Before the era of the tabloid, New Yorkers got their gossip fix from a publication known as Town Topics, where the shocking secrets of the Gilded Age were revealed. But its publisher, William D'Alton Mann, was into more than just a bit of sleaze; he used these scandalous revelations to blackmail members of New York’s high society.

In this very special presentation of the Gilded Gentleman podcast, Carl Raymond and his special guest, Vanity Fair writer Joe Pompeo, introduce you to this forgotten scheme which threatened to tear apart the morals and polite mannerisms of Gilded Age society. 

And for more adventures through Gilded Age New York, check out the Gilded Gentleman podcast, wherever you get your podcasts.

This show was produced and edited by Kieran Gannon

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Our book, The Bowery Boys Adventures in Old New York, was just re-released as a 10th-anniversary edition with lots of brand-new entries. So to celebrate, we thought we would highlight three of our all-time favorite stories from the book. Featuring:

— The Astor House, one of the first luxury hotels in the United States, owned by the original Astor himself — John Jacob Astor. When it opened in 1836, it wrote the rules for how people even stay in hotels in New York City. Why was it considered so revolutionary during its day, and why did its eventual demolition in the 20th century take almost 13 years?

— The Haymarket, the most scandalous dance hall of the Gilded Age! This lively and bawdy place, where both men and women met (sometimes upstairs, behind the curtains), sat in the heart of New York’s turn-of-the-century entertainment district, the burgeoning theater district. But the show inside was MUCH more risque. Oh-la-la! Tom gives you a little tour of the joint, so pull up your stockings.

— The Nabisco Factory in the Meatpacking District was New York’s very own Willie Wonka’s chocolate wonderland, the American center of cookie and cracker making for decades. The sweet smells from the National Baking Company’s ovens were a relief in the late 19th-century district of meat processing. It was here that two of the most important manufactured desserts in American history were born. Visitors to the High Lineand Chelsea Market may not realize they are strolling through a veritable cookie paradise!

This episode was produced and edited by Kieran Gannon

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It’s a scene more commonly imagined today in a Wild West saloon -- a shootout at Stanwyx Hall, across from the most elegant hotel in New York. The year was 1855, and the combatants were bitter rivals who had fought many times, including once in the notorious neighborhood of Five Points.

By the end, one man lie bleeding on the floor -- William Poole, a member of the Bowery Boys street gang, better known as Bill the Butcher.

The Martin Scorsese film Gangs of New York, loosely based upon the Herbert Asbury book, features a version of this character (named Wiiliam Cutting) played by Daniel Day-Lewis. But the story of the real William Poole is far more fascinating, stretching from the west side's Washington Market to the streets of today's SoHo neighborhood.

In this episode, Greg takes you into the world of Bill Poole and the domain of the mid-19th century street gang, mostly seen as scourges of the public good -- that is, until ruthless politicians began to see them as useful.

What was the Bowery like in the 1840s? And just who were the Bowery Boys?

This episode was produced and edited by Kieran Gannon.

Visit our website for more episodes related to this one and some additional images.

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Alexander Hamilton vs Aaron Burr! Delmonico's vs Sherry's! John Adams vs everybody! Some of history's most fascinating stories involve important figures who did not like each other very much.

In this edition of Bowery Boys History Live!, recorded at Manhattan's City Winery on May 26, 2026, Greg Young from the Bowery Boys brings some of these stories to a live audience, featuring author Laurie Gwen Shapiro, tour guide Billy Nemec, and the Gilded Gentleman himself, Carl Raymond.

Featuring tales of Revolutionary War spite, obscene Gilded Age banquets, and Jazz Age flights of spite. PLUS: New York City's longest-running rival.

NOTE: We performed at City Winery less than 24 hours after the Knicks clinched their place in the NBA Finals.

This episode for produced and cleaned up by Kieran Gannon.

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Bowling Green is best known today as the calming, flower-filled oasis in lower Manhattan, next to the decidedly less calming, lumbering sculpture Charging Bull, which is popular with tourists. But this peaceful park was once home to New York City’s most infamous statue -- and the stage for America's first No Kings protest.

In 1770, the old park became the home of a monumental statue of King George III on horseback, an ostentatious artifact meant to remind the rebellious colonists of just who was in charge.

On July 9, 1776, following a reading of the freshly minted Declaration of Independence, angry New Yorkers violently pulled down that statue of King George and, as legend has it, rendered his body into bullets used in the battles of the Revolutionary War. 

As we approach the 250th anniversary of the United States, we also mark the 250th anniversary of this event — not a moment of jubilation and freedom, but of anger and uncertainty. The Declaration beautifully set down the words of independence. The tearing down of King George  made the same statement — in a far messier, more violent manner.

In this episode, take a trip back to the city right before the war, when New York was split into those sympathetic to the Tories and those to the Sons of Liberty, an early organization dedicated to the liberty of the American colonies.

PLUS: Find out where you can locate artifacts from this story throughout the city today.

FEATURING: A young Alexander Hamilton, William Pitt the Elder, that rascal Cadwallader Colden and the enterprising ladies of the Wolcott household.

This special episode is not a rerun! It's a riff on a 2020 Bowery Boys episode. It has been rewritten and rerecorded (including for video on YouTube) in honor of America 250, and newly produced and edited by Kieran Gannon.

Visit the website for images and other podcasts associated with this show. 

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