Summary of "William J. Sharkey’s Not-so-great Escape" Stuff You Missed in History Class
Hosts: Holly Fry & Tracy V. Wilson
Release Date: August 13, 2025

Introduction

In the episode titled "William J. Sharkey’s Not-so-great Escape," hosts Holly Fry and Tracy V. Wilson delve into the tumultuous life of William Jay Sharkey—an infamous 19th-century pickpocket, con man, politician, and murderer whose dramatic escape from New York City's Tombs prison remains shrouded in mystery.

Early Life and Criminal Endeavors

William Jay Sharkey, born in the late 1840s, began his life on a troublesome path early on. Initially gaining notoriety as an expert pickpocket specializing in stealing fine jewelry, Sharkey's knack for crime did not wane even after his first arrest for stealing a pocketbook. His relentless pursuit of a life of crime led him to intertwine with the influential political machine of Tammany Hall under William "Boss" Tweed.

"Sharkey was the son of respected residents of the Ninth Ward, but he went astray early in life and after a brilliantly notorious career of the crooked sort, bloomed out into a successful political adventurer."
— Tracy V. Wilson [03:22]

Sharkey's rise within Tammany Hall saw him become a significant player in the 8th Ward primaries, leading to the establishment of his own club and membership in various influential political organizations within the 5th congressional district. However, his political fortunes waned, leading him back into his criminal pursuits.

The Murder of Robert Dunn

In 1872, Sharkey's gambling ventures took a disastrous turn in Buffalo, where he initiated a game called Pharaoh Bank—a popular card game of the era intended for gambling. After suffering substantial losses totaling $4,000 in five days, Sharkey sought to recoup his losses by funding a new Pharaoh Bank operation through his associate, Robert Dunn. Unfortunately, Dunn's venture quickly mirrored Sharkey's earlier failures.

The tension between Sharkey and Dunn culminated on September 1, 1872, following the funeral of their mutual associate, James Riley. At a saloon on Hudson Street known as "the Place," Sharkey confronted Dunn over the unpaid $600 seed money. The confrontation escalated, leading Sharkey to fatally shoot Dunn.

"Billy, put that away. It might go off and shoot somebody."
— William Welsh, Eyewitness [08:32]

The Trial: Accusations of Accidental Murder

Sharkey's trial, which began nearly ten months after the murder, became a focal point of intense public scrutiny. Faced with eyewitness testimonies placing him at the scene, Sharkey's defense contended that the shooting was accidental. According to one defense attorney, Charles Brooklyn, Sharkey was engaged in a dramatic gesture to illustrate his loyalty and inadvertently discharged the firearm.

"There was a time I would go into a butcher shop and let a butcher take a cleaver and cut that arm off for that son of a bee."
— William Welsh, Eyewitness [09:00]

Despite testimonies supporting both the prosecution's claim of intentional murder and the defense's argument of an accidental discharge, the jury found Sharkey guilty of first-degree murder. The judge, emphasizing Sharkey's intoxicated state during the incident, sentenced him to death by hanging.

"Voluntary intoxication can furnish no excuse or immunity to crimes. And so long as the offender is capable of conceiving a design, he will be presumed, in the absence of contrary proofs, to have intended the natural consequences of his own acts."
— Judge [19:04]

Imprisonment and the Tombs

Sharkey was incarcerated in the Manhattan House of Detention, colloquially known as "the Tombs." Due to his connections with Tammany Hall, Sharkey enjoyed privileges uncommon to typical inmates. His girlfriend—or possibly wife—Maggie Jordan became a constant presence, ensuring he had comforts akin to home, including fine furnishings and even a pet canary.

The Great Escape

On November 19, 1873, under mysterious circumstances, Sharkey orchestrated a daring escape from the Tombs. The escape involved Maggie Jordan disguising Sharkey and smuggling him out of prison. Reports indicate that Sharkey shaved off his mustache and concealed his clothing to facilitate the break.

"At first, reports of the escape were met with disbelief. It seemed so preposterous and even humorous."
— Tracy V. Wilson [35:41]

Despite a substantial reward of $2,000 for his capture, Sharkey eluded authorities, using his political connections to navigate his newfound freedom.

Life Beyond the Tombs

Sharkey fled to Cuba, where he initially found some semblance of restraint compared to his notorious behavior in New York. However, his life took a downward turn following his separation from Maggie Jordan. Various accounts suggest he lived under the alias Frank Campbell, continuing to assert that Dunn's death was accidental. Eventually, Sharkey was arrested in Cuba for threatening the captain and purser of a ship, leading to his return being attempted by the United States. However, without an extradition treaty between the U.S. and Spain at the time, Sharkey's fate became increasingly uncertain.

"Sharkey has more respect for the authorities in Havana than he ever showed for the police in New York and carefully represses himself when there is the slightest danger."
— Harry Davies, Private Detective [37:08]

Reports from Europe in the early 1900s suggested various fates for Sharkey, including joining the Spanish military or dying in Italy, but none were substantiated. His ultimate whereabouts and fate remain unknown to this day.

Maggie Jordan’s Aftermath

Maggie Jordan, deeply involved in Sharkey's life and his escape, eventually married actor William J. Scanlon. Their marriage was tumultuous, with Scanlon being declared insane and committed to Bloomingdale Asylum in 1892. Maggie remained a figure entwined with Sharkey’s legacy until her death in 1898.

Conclusion

William J. Sharkey's life is a testament to the turbulent interplay between crime, politics, and corruption in 19th-century New York. His audacious escape from the Tombs and subsequent disappearance cemented his status as one of the era's most enigmatic criminals. The mystery surrounding his fate continues to intrigue historians and enthusiasts alike.

Notable Quotes

• "Sharkey was the son of respected residents of the Ninth Ward, but he went astray early in life..." — Tracy V. Wilson [03:22]
• "There was a time I would go into a butcher shop and let a butcher take a cleaver and cut that arm off for that son of a bee." — William Welsh [09:00]
• "Voluntary intoxication can furnish no excuse or immunity to crimes..." — Judge [19:04]
• "At first, reports of the escape were met with disbelief. It seemed so preposterous and even humorous." — Tracy V. Wilson [35:41]
• "Sharkey has more respect for the authorities in Havana than he ever showed for the police in New York..." — Harry Davies [37:08]

This comprehensive exploration of William J. Sharkey's life offers listeners a deep dive into a fascinating chapter of New York's criminal history, combining meticulous research with engaging storytelling to illuminate the complexities of Sharkey's character and the enigmatic escape that defined his legacy.