Short History Of...

The Pinkerton Detective Agency

Host: John Hopkins
Guest Expert: Rodri Jeffrey Jones, historian and author
Date: November 17, 2025

Main Theme / Purpose

This episode explores the remarkable and controversial history of the Pinkerton Detective Agency—America’s first and most famous private detective agency. The story covers the journey of its founder, Allan Pinkerton, from radical Scottish immigrant to the creator of a powerful private security force. It delves into the agency's methods, high-profile cases, role in shaping private policing, involvement in anti-union activity, and its lasting legacy in American culture and law enforcement.

Key Discussion Points & Insights

1. Allan Pinkerton’s Early Life and Ideological Influences

• Born in 1819 in a poor family in Glasgow, Scotland. Raised in extreme poverty amid radical politics, shaping his lifelong wariness of authority and passion for reform.
• Apprenticed as a cooper (barrel maker), Pinkerton was exposed to radical ideas about workers' rights and joined the Chartist movement—eventually becoming part of its revolutionary wing.
  • Quote:
    “He became radicalized and joined the Chartist movement... a leading voice in the revolutionary wing.”
    — Rodri Jeffrey Jones, 07:40
• Possible reasons for emigration: escaping prosecution for Chartist activity or hiding after being discovered as a police informer (both theories discussed, with Pinkerton himself remaining an enigmatic figure).

2. Migration to America & Path to Detective Work

• Emigrated to America in 1842 with his young wife, initially working as a cooper in Dundee, Illinois.
• Stumbled onto counterfeiters while searching for wood, leading to his first major investigation, which earned him trust among local bankers.
  • Dramatic anecdote: Pinkerton investigates a curious island campfire, discovers counterfeiting, leads to arrests—an event he later describes as the end of his barrel-making days and the start of his detective career.
    (Narrator, 00:43–09:03)
• Appointed deputy sheriff due to his aptitude, then moved to Chicago.

3. Founding the Pinkerton National Detective Agency

• 1850: Pinkerton founds the Pinkerton National Detective Agency—the first of its kind.
  • Notable for its “We Never Sleep” motto and the wide-open eye logo (possibly the origin of “private eye”).
  • Early clients: banks, railroads, insurance companies—entities most harmed by theft and fraud in a country lacking a federal police force.

4. Early Investigations & Undercover Methods

• Pinkerton agents engage in complex operations such as:
  • Catching conductors’ ticket scams on the Illinois Central Railroad—commissioned via Abraham Lincoln (then legal counsel for the railroad).
  • Developing rigorous undercover techniques, discipline, and cross-jurisdiction work—innovations later borrowed by government agencies.
• Personal connection forms between Pinkerton and Lincoln, rooted in shared abolitionist beliefs. Pinkerton involves himself and his agents in the Underground Railroad, aiding enslaved people to escape (16:40).

5. Protecting Abraham Lincoln & The Baltimore Assassination Plot (1861)

• Pinkerton uncovers a credible assassination plot against President-elect Lincoln in Baltimore.
• Orchestrates an undercover operation involving agent Kate Warne (America’s first female detective) and himself, spiriting Lincoln to Washington in disguise.
  • Quote:
    “I think that Pinkerton was absolutely right to take these as precautions. The feeling against Lincoln was so strong...”
    — Rodri Jeffrey Jones, 23:23
• The success leads to mocking in the press but marks a turning point in presidential security and highlights the dangers of political violence.

6. The Civil War Years

• Pinkerton is tasked by Lincoln to create an intelligence and security network for the Union, guarding railroads, gathering intelligence, and operating behind Confederate lines.
• The agency’s nationwide reach and capabilities are proven, and it earns a reputation as a private law enforcement powerhouse.

7. Outlaws of the West: Jesse James, Butch Cassidy, and the Rise of the Private Manhunt

• The agency is contracted to pursue notorious outlaws:
  • Jesse James and the James-Younger Gang, Butch Cassidy’s Wild Bunch, and others.
  • Pinkerton innovates by collecting photographic mugshots—a precursor to modern criminal identification techniques used by the FBI and CIA.
  • Notoriously, the failed raid on Jesse James’ family farm results in civilian casualties and massive public backlash (Archie James killed, Zerelda James maimed), burning the Pinkerton name as both lawmen and villains.
  • Quote:
    “They did steal from the rich, but they didn’t give it to the poor. But they were heroes partly because of the people that they robbed... typically railroads and banks.”
    — Rodri Jeffrey Jones, 30:05
• The Pinkertons are depicted in Western lore as relentless antagonists—the inspiration for countless "private eye" archetypes.

8. The Dark Turn: Strikebreaking and Anti-Union Work

• In a sharp contradiction to Pinkerton’s own radical roots, the agency becomes infamous for anti-union activities:
  • Employed by corporations to infiltrate unions, break strikes, and "protect property"—frequently through violence and intimidation.
  • The 1892 Homestead Strike becomes a national scandal. Hundreds of Pinkerton agents, hired by Carnegie Steel, engage in a bloody clash with striking workers. The Pinkertons are seen as corporate mercenaries.
    • Quote:
      “You could say it’s hypocrisy... he did have a rationale that unionism and strike action... involved coercion and violence. Now this is definitely a contradiction in his personality.”
      — Rodri Jeffrey Jones, 38:17
  • Resulting outrage leads to the Anti-Pinkerton Act (1893), which bans the federal government from hiring private detective agencies—symbolizing a deep distrust of private armies serving corporate interests.

9. Decline, Reinvention, and Enduring Legacy

• As public policing becomes professionalized, Pinkertons’ shadow army model declines.
• Agency shifts focus to private security, investigations, and risk management; merges into Securitas (still operates under Pinkerton name in global security sector).
  • Quote:
    “Labour work accounted for at least one third of the income of the Pinkerton Agency over a long period. That’s a huge proportion...”
    — Rodri Jeffrey Jones, 49:59
• The agency’s history raises ongoing questions about private versus public law enforcement, corporate power, labor rights, and limits of civil liberties—a legacy that remains relevant today.
  • Quote:
    “The private detective is, of his nature, an ambivalent person. And that interests us because... that's a widespread aspect of human nature.”
    — Rodri Jeffrey Jones, 52:32

Memorable Moments & Notable Quotes

• The origin story: Pinkerton's encounter with counterfeiters by chance, deciding to become a detective. (00:43)
• A pioneering female detective: Kate Warne’s hiring and vital role in the Baltimore plot.
  “She could go places where men can’t... He hired her on the spot, making her America’s first female private detective.” (19:42)
• Outlaw mugshots: Jesse James and Butch Cassidy’s gangs posing for formal photographs, inadvertently handing the Pinkertons tools for modern criminal databases. (30:28, 36:12)
• Violent strikebreaking: The Homestead riot’s vivid scenes—Pinkertons arriving on barges, gunfire, collapse of the strike.
  “The sight of hired gunmen putting down American workers on American soil is deeply unsettling to many citizens.” (46:25)
• America’s detective archetype: The Pinkertons' image setting the stage for the "private eye"—equal parts relentless, cunning, and ambiguous.

Timestamps for Key Segments

• Pinkerton’s Radical Past in Scotland: 07:40–09:03
• First Detective Work / Dundee Counterfeiters: 09:35–11:04
• Chicago, Deputy Sheriff and Founding of Agency: 11:56–12:39
• Railroad Fraud, Lincoln Connection: 15:36–16:40
• Abolitionist Work and the Underground Railroad: 16:40
• Baltimore Assassination Plot & Lincoln’s Secret Passage: 18:59–23:46
• Civil War Intelligence Roles: 23:46–25:03
• Pursuit of Jesse James & Notorious Outlaw Gangs: 30:28–36:12
• Anti-Union Activities, Strikebreaking & Homestead: 38:17–45:22
• Anti-Pinkerton Act & Decline: 46:25–48:34
• Transformation into Modern Security Firm: 49:59–50:36
• Reflection on Ambiguity of Private Detectives: 52:32–53:06

Tone & Language

• The episode blends vivid narrative storytelling (especially when depicting raids, chases, or crime scenes) with commentary and analysis by historians, particularly Rodri Jeffrey Jones, whose insights ground the narrative with context and judgment.
• Tone is inquisitive, sometimes dramatic, highlighting moral ambiguities and political contradictions.

Conclusion

This episode reveals the Pinkerton Detective Agency as a vital—but deeply ambivalent—pillar in American history. From abolitionist beginnings and the daring foiling of assassination plots to their controversial role as corporate enforcers against labor, the legacy of Allan Pinkerton and his agency is still felt today—in our laws, our police forces, and the very image of the detective in American culture.

As brilliantly encapsulated by historian Rodri Jeffrey Jones:

“The private detective is, of his nature, an ambivalent person... And that interests us because that's a widespread aspect of human nature.” (52:32)

If you enjoyed this, the podcast recommends delving deeper into the “Baltimore Plot” and Pinkerton’s cunning via the Noiser “Detectives Don’t Sleep” series.