The Dollop with Dave Anthony and Gareth Reynolds
Episode: Saloon Owner Billy McGlory (March 31, 2026)
Host: All Things Comedy

Overview

In this episode of The Dollop, comedians Dave Anthony and Gareth Reynolds dig into the wild and tumultuous life of William H. “Billy” McGlory, a notorious saloon owner in 19th-century New York City. As always, Dave shares the story—rife with crime, vice, and underworld antics—with Gareth reacting blindly, leading to classic riffing, dark humor, and insightful commentary about corruption, poverty, and the mechanics of vice in Gilded Age America.

Key Discussion Points & Insights

1. Billy McGlory’s Origins and Early Life (Starts ~02:03)

• Born William H. McGrory/McGlory in Manhattan’s infamous Five Points to Irish immigrants, Patrick and Honora.
• Father died when Billy was 8; mother struggled to support family, took in boarders, remarried several times.
• Billy entered a world of petty crime as a teenager, running with pickpockets and thieves, possibly part of a gang in the 4th and 6th Wards.
• Use of multiple aliases, e.g., Gilbert McGlair, "Gilly McGlory" ([04:35]).

Notable banter:
Gareth, riffing on Victorian crime tropes:

“The Oliver fan in me always wanted to be a part of that… hang out with an older man who showed me how to pickpocket… throw our fencing materials in a pile…” ([03:59])

2. First Robbery and Jail Time (04:35–06:15)

• Convicted of first-degree robbery at 16, did 5 years in Sing Sing prison, where he met more criminals.
• Physical description: “Long wavy hair and a ministerial look” ([07:03]).

3. Entry into the Saloon Business—The Burnt Rag (06:51–22:01)

• Post-prison, opens “The Burnt Rag” at 103 Bowery St.—poorly named, “chloroformy,” as Gareth jokes ([06:51]).
• Fires, shifting locations, always at the center of criminal activity.
• Became a den for thieves, sex workers, and the “lower end of society”—just blocks from the police precinct.
• Repeated police raids over liquor law violations and violent incidents.
• Customers would be “plied with booze,” then drugged, robbed, assaulted by bouncers.

Quip:

"If I’m gonna lose money, I want sex." — Gareth ([08:49])

• The Burnt Rag became notorious in police records and press (“Burnt Rag Again” headlines, regular raids, legal troubles).

4. Family and Criminal Entanglements (10:47–15:08)

• Family members involved: half-brother Johnny Thompson (actor), half-sister Honora (married thief Hugh Campbell), sister Maryanne.
• Episodes of family violence, such as the 2 a.m. brawl where Billy knocked out three of his sister’s teeth ([14:24]).

5. Bar Fights, Beatings, and the Downfall of the Burnt Rag (15:20–22:01)

• Example: Billy justifies beating Henry Snyder with a chair as “self-defense”; later, witnesses vanish under suspicious circumstances ([15:20]).
• The bar’s reputation is cemented by press coverage of fights and brutal robberies.
• Notable incident: After a man is beaten and held at a restaurant “maybe to get ransom,” the authorities finally pull the Burnt Rag’s license ([22:01]).
• Classic Dollop riff:

“What are we doing here? Good Lord, where’s the justice? The judge was like, no, that’s insane. That’s not how it works…” — Dave ([22:34])

6. Armory Hall: Notorious New Venue (23:03–36:33)

• Opens “Armory Hall” on Hester St.—becomes one of NYC’s most infamous dives.
• Features: Cancan dancers, boxing matches, “boxes” for sex work, all-night drinking, gay-friendly staff and clientele.
• “Rules”: No robberies inside, but once patrons were tossed outside, all bets were off—robbed naked, everything gone ([24:10]).

Memorable exchange:

“Once outside, they could literally be robbed of everything. And it was very common for them to be stripped naked.” — Dave
“I like that move… makes you not want to fight anything, you know what I mean?” — Gareth ([24:20])

• Gareth, mocking the constant brawling:

“Why would you go there? …I don’t know, they’re robbing people pretty hard here, but at least the girls will do a foot job.” ([26:50])

• National press described the scene as “a beastliness and depravity compared with which no chapter in the world’s history is equal” ([27:35]).

7. Battles with Authorities and the Law (36:33–45:02)

• As reform mayors wage war on vice, McGlory’s political connections (Tammany Hall) stymie closure attempts.
• Finally, under growing pressure and reform laws, McGlory is tried, convicted in 7 minutes ([44:16]), and sentenced to a year hard labor for running a “disorderly house.”
• “Several people testified, including a florist he ordered plants from but never paid…”
• Banned from opening a New York saloon until 1896.

8. Attempts at Respectability and Recurrent Scandals (45:02–54:00)

• Joins the Salvation Army, claims to support temperance, flips positions repeatedly.
• Tries and fails at various “respectable” businesses, continually targeted by the press and public.
• Buys a temperance resort in Syracuse, sparking civic panic. Locals form a “Law and Order League” to stop him ([55:13]).
• Sells property after the venture flops.

9. Later Life and Decline (54:00–62:00)

• Multiple failed attempts to open new establishments; dogged by creditors and legal trouble.
• Eventually found living in poverty; may have died in the Bronx or Orlando; exact date unknown.
• Final years marred by family lawsuits and attempts to seize his mother’s property.

Notable Quotes & Banter

• “It’s amazing how long we’ve been trying to figure out… why everything’s so crazy… and it’s always just money.”
  — Gareth ([42:38])

• “He’s just changed… Like he’s punching them in the mouth, right? Like they came after him and he’s like, all right, how about I show you how it works?”
  — Dave on McGlory moving the vice operation uptown ([41:26])

• “Welcome to Peto [sic] Island.” — Gareth, shuddering at temperance resorts doubling as child-safe amusement parks ([54:01])

• “He does that to elicit sympathy. And then they still do the evil thing… [like] Elon, Trump… they always posture like they’re going to have a change of heart.” — Gareth ([55:53])

Timestamps of Key Segments

• 02:03 – Billy’s childhood and entry into crime
• 04:35 – First robbery, aliases, and prison stint
• 06:51 – The Burnt Rag: opening and criminal business model
• 09:44 – Press and police attention
• 13:23 – Family court brawl and violence
• 15:20 – Notable bar fights and suspicious disappearance
• 22:01 – Burnt Rag closed after kidnapping/assaults
• 23:03 – Launch of Armory Hall (“hot joint”) and its infamy
• 27:59 – Description by out-of-town reporters
• 36:33 – Reformers vs. McGlory; his courtroom appearance and conviction
• 41:26 – Buying Hotel Irving, flaunting to the authorities
• 54:00 – The failed Syracuse temperance project & subsequent decline
• 59:38 – Final closure of Elmwood Park and McGlory’s disappearance from public life
• 62:21 – Episode close & hosts’ wrap-up

Tone and Style

• Irreverent, biting, darkly comic; hosts interweave historical recounting with modern analogies and satirical quips.
• Social commentary about class, corruption, and American moral panics runs throughout.
• The “Van Edition” brings in road-trip asides, adding a low-key, conversational atmosphere.

Conclusion

The tale of Billy McGlory is a microcosm of vice, survival, and reinvention in Gilded Age New York—a world where criminality and commerce were deeply entwined, and where notoriety brought both fortune and constant scrutiny. Dave and Gareth turn this history into a wild ride through American hypocrisy and the roots of urban infamy, never missing a beat for a joke or a pointed observation.

For more wild stories from American history, visit the Dollop archives or subscribe for new episodes each week!