The Original Detective Agency

Long before the FBI existed, the Pinkerton National Detective Agency was the go-to force for anyone needing to track down a train robber or infiltrate a secret society. Founded by Allan Pinkerton in the mid-19th century, this private security firm became famous for its relentless pursuit of outlaws and its iconic logo of an open eye. You might think of them as the original private eyes who basically wrote the playbook for modern investigation and surveillance.

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1. Thwarting the Baltimore Plot

Before Abraham Lincoln could even take his first oath of office, Allan Pinkerton uncovered a dangerous conspiracy to assassinate him during his train trip to Washington. The detectives worked undercover in Baltimore to gather intel and eventually spirited the President-elect through the city in the middle of the night. It's wild to realize that the course of the Civil War might’ve been completely different if these agents hadn't been so paranoid about security.

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2. Hunting the Reno Brothers

When notorious train robbers known as the Reno Brothers hit the Midwest, they didn’t expect the Pinkerton agency to come after them across state lines. Pinkerton agents tracked them throughout the Midwest and were able to arrest key members of the Reno family in Indiana. The case made the Pinkertons famous for never letting a perpetrator escape justice.

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3. Infiltrating the Molly Maguires

Pinkerton agent James McParland spent two years undercover as a coal miner to infiltrate a secret criminal organization in Pennsylvania. His cover was so good that he became a confidant of the Molly Maguires and helped convict them of assault. He is just one example of many Pinkerton agents who went undercover to infiltrate criminal organizations.

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4. Chasing the James-Younger Gang

Jesse James was one of the most well-known outlaws of his time, and stopping him was one of the agency’s biggest challenges. The Pinkerton detectives spent years trying to bring the Jesse James gang to justice after several robberies. Although they never caught Jesse James, they were able to disrupt his operation and force him into hiding.

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5. The Great Train Robbery of 1870

The Central Pacific Railroad hired the Pinkerton agency after a large sum of money was stolen from their express car. Tracking them down wasn’t easy, but thanks to forensic evidence and suspect interviews, they were eventually able to track them down in the mountains.

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6. Protecting the Homestead Strike

During a labor strike at a steel mill in 1892, the Pinkerton agency was hired to protect the building and its valuable contents. They ended up getting bombarded by stones and other projectiles during a standoff on the riverbank. It destroyed any goodwill the Pinkerton agency had gained with the working man.

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7. Following the Butch Cassidy Trail

Known as the Wild Bunch, Butch Cassidy was part of a group of outlaws that kept Pinkerton agents busy for years. Eventually, Butch Cassidy and his companion Sundance Kid rode out of the country to avoid Pinkerton agents. Tracking down outlaws across the entire American West is one way to pay the bills.

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8. Recovering the Gainsborough Painting

The Pinkerton agency wasn’t always tracking outlaws and train robbers; they recovered a stolen portrait of the Duchess of Devonshire. An agent spent years tracking down an international gang of art thieves until he found it hidden in a Chicago hotel room.

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9. The Capture of Oliver Curtis Perry

Oliver Curtis Perry was a train robber who learned about Pinkerton agents when he attempted to rob the same train twice. After agents caught up with him in a standoff, he spent the rest of his life in prison. Who doesn’t love a good train robbery gone wrong?

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10. Solving the First National Bank Theft

When over one hundred thousand dollars vanished from a bank vault in New England, the detectives used a series of clever interviews to pinpoint the thief. They discovered that an employee had been living a double life and managed to recover most of the stolen funds before they were spent. It’s a classic example of how their methodical approach to paperwork could be just as effective as a fight.

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11. Stalking the Sundance Kid

If you thought Butch Cassidy was the only outlaw the Pinkerton agency chased, think again. The Sundance Kid’s real name was Harry Longabaugh, and he was a top target for the Pinkerton agency as well. By using photography and wanted posters, the Pinkerton agency tracked him wherever he went.

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12. The Case of the Counterfeiters

By helping the government catch counterfeiters, the Pinkerton agency proved they could handle white-collar crime as well. By posing as strangers, they eventually discovered the master engraver who led the ring. Pinkerton agents helped shape and define many of the techniques used by the Secret Service today.

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13. Guarding the Diamond Mines

When investors were swindled into thinking that California had large diamond mines, they hired the Pinkerton agency to validate the claim. The “mine” was found to be filled with industrial diamonds, a scam referred to as “salting” a mine. The Pinkerton agency saved investors a lot of money that year.

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14. Tracking the Rube Burrows Gang

If you were robbing trains in the South around the turn of the century, you might have run into Rube Burrows. A wanted train robber in multiple states, Rube Burrows was eventually caught in a swamp by Pinkerton agents. Although he put up a fight, Burrows was caught and spent the rest of his life in prison.

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15. The Mystery of the Missing Payroll

A massive payroll intended for workers at a mine once went missing, causing panic that the workers would revolt. When the Pinkerton agency arrived, they discovered it was hidden in a tree stump on the payroll custodian’s property. Always check trees when you’re trying to find stolen money.

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16. Protecting the Spanish Royalty

The Pinkerton agency became internationally known when they provided security to Spain’s royalty during their visit. Thousands of guests and heightened media attention didn’t stop the Pinkertons from providing security during the state visit. If you can handle protecting a queen, your corporate security job is sure to be a piece of cake.

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17. The Infiltration of the Steunenberg Assassins

After a former Idaho governor was assassinated by a bomb, the agency sent James McParland to investigate the radical labor leaders suspected of the crime. The case led to a sensational trial that highlighted the ongoing tension between big industry and unions. It’s often cited as one of the most significant legal battles that the agency ever helped build.

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18. Busting the Night Riders

During the early 1900s, Kentucky and Tennessee farmers hired the Pinkerton agency to protect their property from the Night Riders. By working with federal officials, Pinkerton agents helped convict the heads of the group and restore order. Their ability to blend with the locals and protect assets shows their versatility.

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19. The Recovery of the Bidwell Fortune

Two brothers managed to defraud the Bank of England of an enormous sum of money before fleeing back to the United States. The Pinkertons were hired to find them and tracked the duo through a series of aliases and luxury hotels. They eventually caught the brothers.

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20. Safeguarding the 1893 World's Fair

Serving as security at the Chicago World’s Fair was a massive opportunity for the Pinkerton agency. Handling thousands of guests and preventing any major incidents for months on end was no easy task. If you can handle security at the World’s Fair, you can handle anything mother corporation assigns you.

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