Stuff You Should Know: The Pinkerton Detective Agency

Episode Title: The Pinkerton Detective Agency
Release Date: April 3, 2025
Hosts: Josh Clark and Chuck Bryant
Production: iHeartPodcasts

Introduction to the Pinkerton Detective Agency

In this engaging episode of Stuff You Should Know, hosts Josh Clark and Chuck Bryant delve deep into the storied history of the Pinkerton National Detective Agency. They explore the agency's origins, its rise to prominence, and the complex legacy it left behind. Through a blend of historical facts and entertaining banter, Josh and Chuck provide listeners with a comprehensive understanding of the Pinkertons’ impact on American society.

Alan Pinkerton: Origins and Early Career

The story begins in 1819 in Scotland, where Alan Pinkerton was born into a family with strong law enforcement ties—his father was a police sergeant. As Chuck notes, "the Pinkertons are just so legendary, you know, like everybody knows what the Pinkertons are" (02:14).

At the age of 23, in 1842, Pinkerton immigrated to the United States, settling in Chicago. Initially, he pursued the trade of a cooper, making barrels, a skill he honed back in Scotland. However, his career took a pivotal turn when he discovered a hideout of counterfeiters while cutting wood for barrels. Demonstrating his knack for detection, Pinkerton rallied local citizens to capture the criminals, garnering significant local recognition. This led to his appointment as deputy sheriff in Kane County, Illinois, in 1846.

Abolitionism and the Underground Railroad

From the outset, Pinkerton’s agency was involved in noble causes. From 1850, the Pinkerton National Detective Agency actively supported the abolitionist movement, aiding in the escape and freeing of enslaved individuals. As Josh explains, Alan Pinkerton worked to "assist the escape and freeing of enslaved people," even volunteering a stop on the Underground Railroad (08:45).

Pinkerton’s close friendship with John Brown, the famous white abolitionist, underscored his commitment. Together, they orchestrated daring rescues, such as assisting Brown's raid in Missouri, which resulted in the liberation of 11 enslaved people. Pinkerton financed their train ride from Chicago to Detroit, showcasing his dedication to the cause.

Innovations: Hiring Kate Warne

One of the most groundbreaking aspects of the Pinkerton Agency was the hiring of Kate Warne, the first female detective in the United States. In 1856, after Warne persuaded Pinkerton of the unique capabilities women could bring to undercover operations, he hired her. By 1860, Warne was the head of the female detective bureau, making the Pinkerton Agency a pioneer in gender-inclusive law enforcement.

Josh highlights, "she was the first sworn policewoman in the United States" long before official recognition came, demonstrating Pinkerton’s forward-thinking approach (18:16).

Role in the Civil War

With the outbreak of the Civil War, the Pinkerton Agency's influence expanded significantly. Abraham Lincoln, impressed by Pinkerton’s work with railroads, appointed him as the head of the Army of the Potomac’s intelligence division. Alan Pinkerton played a crucial role in uncovering Confederate spy rings, notably dismantling Rose O'Neill Greenhow’s espionage network (22:22).

However, Pinkerton's intelligence gathering had its flaws. He famously overestimated Confederate troop numbers, reporting up to 200,000 troops when General Robert E. Lee commanded only around 45,000. This critical miscalculation led to General George B. McClellan's cautious strategies, potentially prolonging the war unnecessarily. As Chuck remarks, Pinkerton "grossly overestimated" the troop strength (23:02).

Post-War Pursuits: Outlaw Hunting

After the Civil War, the Pinkerton Agency shifted focus to tracking outlaws in the rapidly expanding American West. They became renowned for pursuing notorious gangs like the Reno Gang, who were responsible for numerous train and bank robberies. The Pinkertons' relentless pursuit techniques—often tracking suspects across vast distances into Canada and Mexico—cemented their reputation as formidable detectives.

“We hire agents who won’t give up until they catch the person,” Chuck emphasizes, highlighting the agency’s dogged persistence (27:53).

Notable Cases: The Reno Gang and the James Gang

One of the Pinkertons' early successes involved dismantling the Reno Gang, who had amassed half a million dollars through their criminal activities in the 1860s. By leveraging their extensive network and investigative prowess, the Pinkertons captured key members, including John Reno and Charles Roseberry, recovering significant amounts of stolen money (32:26).

However, their pursuit of the James Gang, led by Frank and Jesse James, marked a turning point. Despite Pinkerton's determination to capture the James brothers, the mission faced tragic consequences. In 1875, a tragic accident occurred during a Pinkerton raid on the James family home, resulting in the deaths of an eight-year-old boy and the maiming of Jesse James' mother. This incident severely tarnished the agency’s reputation, as it was perceived as an overreach of private law enforcement (38:10).

The Homestead Strike and the Rise of Controversy

The Pinkerton Agency's most infamous involvement came during the Homestead Strike of 1892. Hired by Henry Clay Frick to break the union at Carnegie Steel in Homestead, Pennsylvania, 300 heavily armed Pinkerton agents clashed violently with thousands of strikers and community members. Despite their superior firepower, only a dozen workers lost their lives in a brutal 12-hour battle. The public backlash was immediate and severe, leading Congress to investigate the incident and ultimately outlaw the Pinkertons in Ohio.

As Josh summarizes, "Congress urged states to pass laws to make it so that corporations couldn't hire private companies to break unions" (52:15).

Legacy and Modern Operations

Despite the controversies, the Pinkerton Agency persisted, eventually evolving into a global security firm. Acquired by Securitas in 1999, Pinkerton continues to operate worldwide, providing corporate security services and consulting. Their legacy, marked by both heroic pursuits and contentious labor disputes, remains a significant chapter in American history.

Josh notes, "they trade on the name still for sure," referring to Pinkerton’s enduring brand in modern security operations (52:38).

Conclusion

Josh and Chuck wrap up the episode by reflecting on the multifaceted legacy of the Pinkerton Detective Agency. From pioneering detective work and supporting abolitionism to their controversial role in labor disputes, the Pinkertons left an indelible mark on American law enforcement and corporate security practices. The episode serves as a reminder of the complex interplay between private agencies and public interests, highlighting the Pinkertons’ place in history as both protectors and adversaries.

Notable Quotes

• Chuck Bryant at [03:30]: “Either they were pretty great and did some really great work, or they were evil from the start.”

• Josh Clark at [04:05]: “We will partner with local law enforcement when possible.”

• Chuck Bryant at [27:53]: “They would pursue them into Canada, sometimes into Mexico and beyond.”

• Josh Clark at [28:26]: “Best all around boy.”

• Alan Pinkerton at [37:03]: "They must die."

Final Thoughts

Through meticulous research and lively conversation, Josh and Chuck offer listeners a nuanced perspective on the Pinkerton Detective Agency. They balance the agency’s early contributions to law enforcement with the darker aspects of its history, providing a well-rounded exploration of one of America's most enigmatic private detective organizations.

For more fascinating explorations of history and beyond, tune into Stuff You Should Know on the iHeartRadio app, Apple Podcasts, or your favorite podcast platform.