Started by Allan Pinkerton in 1850, the Pinkerton Detective Agency grew so large that it became, at one point in history, the biggest private law enforcement organization in the world. It gained notoriety for being a muscle-for-hire service to industrialists who wanted to deal with pesky strikers and unionists. However, it also handled some thrilling cases where Pinkertons took on some of America’s most infamous criminals.
10. Frank and Jesse James
The infamous Jesse James was once Allan Pinkerton’s number one target. In 1874, he was tasked by the Adams Express Company to bring the James Gang to justice following a train robbery. Pinkerton sent a detective named Joseph Whicher to apprehend the outlaws.
Whicher intended to infiltrate the James farm by posing as a laborer. However, his plan backfired when his true identity was discovered. His body was found just a day later.
Afterwards, Pinkerton sent several operatives who rallied a local posse and went after the gang. However, in a misguided attempt to evacuate people from inside the farmhouse, the Pinkertons threw an incendiary device through a window which injured Jesse’s mother and killed his 8-year-old half-brother Archie. This turned the locals against them and the posse ended up running the detectives out of town. With public opinion not in their favor following the botched raid, Pinkerton decided to stop pursuing the James brothers.
9. The Assassination of Governor Steunenberg
Many Pinkerton detectives had plenty of stories to share, but none more so than James McParland, who tackled some of the agency’s most high-profile cases. In 1905, McParland investigated the assassination of Frank Steunenberg, Governor of Idaho.
The suspect was known as Tom Hogan, but later admitted that his name was Harry Orchard. He made little attempt to conceal his crime and a search of his room uncovered evidence which proved that he built the bomb that killed the governor. However, McParland dug a little deeper and managed to get more information during interrogation. Orchard was born Albert Horsley in Ontario, Canada. He admitted he assassinated the governor for his support of the mining companies under the orders of the Western Federation of Miners (WFM). In fact, Orchard claimed to have killed at least seventeen other people for the WFM.
The bomber directly implicated several prominent labor leaders such as Charles Moyer and William “Big Bill” Haywood and later testified against them in court. They were officially charged with Steunenberg’s murder a year later, but were all acquitted.
8. The Missouri Kid
In early 1903, Pinkerton operative Charles Schumacher was trailing two men who robbed the bank in Union, Missouri of $115,000. His posse finally tracked them down to a farmhouse and demanded their surrender. A gunfight ensued and Schumacher was shot five times and later died of his wounds. Both killers escaped.
After the murder of one of their own, Pinkertons pursued the criminals all over the country, crossing into Canada at times and even posting a lookout in the Philippines. The break in the case came when detectives were able to inspect a house that the two outlaws previously occupied. They discovered a charred but intact piece of paper in the stove. Still legible were the words “George Collins” and “Hartford.” Collins was one of the criminals and Hartford, Connecticut was his hometown. That is where Pinkertons finally caught up to him in March.
His partner-in-crime was 20-year-old William Rudolph, better known as “the Missouri Kid.” He managed to escape prison while George Collins was convicted and hanged. The Kid continued his crime spree for six months before being arrested in Kansas. Rudolph was actually pardoned by the governor so he could go back to Missouri and stand trial for Schumacher’s murder. The Missouri Kid was convicted and executed in May 1905.
7. The Farrington Brothers
While not remembered today as well as other outlaws of the Old West, the gang led by the Farrington Brothers was once one of the most feared in the country. Trained guerillas under Commander Quantrill, Hillary and Levi Farrington took to robbing after the Civil War was over. They were finally arrested by the Pinkertons in 1871 after a gun battle where Hillary shot William Pinkerton in the side.
The criminals were placed on a paddle steamer headed for Columbus, Kentucky. On route, Pinkerton offered Hillary Farrington a drink at the bar. The criminal accepted, but requested to be taken in through the backdoor so people wouldn’t see him in handcuffs.
Of course, this was all a ruse. As soon as he found himself on the deck alone with Pinkerton, Farrington attacked and tried to seize his gun. A fight ensued and, although the killer managed to grab the gun, William Pinkerton landed an uppercut that threw Farrington over the rails and into the churning paddle of the boat, which diced him to bits.
His brother Levi met an equally deadly, but less grisly fate in Tennessee at the hands of a mob seeking justice for his murder of a deputy sheriff.
6. The Gold Bullion Theft
On August 6, 1901, the Selby Smelting & Lead Company’s plant near San Francisco was robbed of 37 bars of gold bullion worth over $280,000. At the time, this was the largest theft of gold bullion in U.S. history.
The thief used a railroad tunnel for access and burrowed underneath the building’s walk-in safe. He then cut a hole in the floor and left with as much gold as he could carry. The investigation was headed by a three-man group consisting of the former police chief, the captain of the detectives, and W.B. Sayers, the superintendent for the Pinkerton San Francisco office. James McParland was brought in on the case and, soon enough, they had a suspect. The cap of Buck Taylor, a former plant employee, was found in the tunnel. He was arrested and a search of his home revealed mud-covered clothes.
Police had enough evidence to convict Taylor, but it was McParland who obtained a confession and, more importantly, the location of the stolen gold. Buck Taylor was actually Jack Winters, a criminal from the East Coast, who gave up where he stashed the bullion in hopes of a more lenient sentence. McParland later wrote in a report that he believed Winters never intended to keep the stolen gold, but rather to “stumble” upon it and return it in exchange for the reward.
5. The Fatty Arbuckle Trial
Arguably, the most famous Pinkerton operative of all time was Sam Hammett, but it had nothing to do with his detective career. After he retired from police work, Hammett changed his first name to Dashiell and wrote detective stories like The Maltese Falcon and The Thin Man. In his previous life, he also helped investigate the Fatty Arbuckle case.
Roscoe Arbuckle was one of the highest-paid stars of the 1910s, but today he is mostly remembered for the shocking end of his career. After a party in November 1921 which caused the death of a young actress named Virginia Rappe, Arbuckle was charged with her rape and manslaughter. In the end, he was acquitted of all charges and issued an apology from the jury.
Rappe died of a ruptured bladder and peritonitis. This was alleged to have happened when the rotund Arbuckle laid down on her. Sordid rumors even claimed that the actor caused the damage when he used a bottle or a piece of ice to penetrate her.
During the trial, his defense team asked the Pinkertons to help prove that Arbuckle was the target of a conspiracy. They showed that Rappe’s party companion and the main witness for the prosecution, Maude Delmont, had a history of extortion and blackmail. Moreover, they proved that Rappe had previous bladder problems which were exacerbated by her drinking bootleg alcohol. This secured Arbuckle’s acquittal, but his career never recovered.
4. The Molly Maguires
Perhaps the most notorious piece of police work conducted by the Pinkertons occurred during the 1870s when James McParland went undercover to take down the Molly Maguires.
The Maguires were a secret group of Irish immigrant coal miners active, mostly, throughout Pennsylvania. At a time when tensions between mine owners and unionists were at their highest, the Molly Maguires took part in numerous violent conflicts. These included sabotage, beatings, and 16 murders, at least.
McParland managed to infiltrate the brotherhood because he could look and act the part. An Irish immigrant himself, the detective posed as a tough murderer-on-the-run named James McKenna. Slowly, but surely, he gained the trust of the Maguires and spent almost three years as one of them, gathering evidence against the organization.
McParland’s efforts led to dozens of arrests. Twenty men were sent to the gallows. The case made McParland famous and even inspired the Sherlock Holmes story The Valley of Fear. Historians later debated some of the detective’s more outlandish accusations and even questioned if he lied on the stand to secure convictions.
3. The Reno Gang
The Reno Gang is remembered today for perpetrating the first train robbery in U.S. history on October 6, 1866. This is only partially correct as it was actually the first robbery of a moving train during peacetime.
After the robbery, detectives led by Allan Pinkerton himself were hot on the trail. They arrested three members of the gang, but charges were dropped after the only witness was gunned down. The gang pulled off several more robberies, traveling from state to state with detectives always right behind them. In Indianapolis, the Pinkertons surrounded and arrested John Reno, one of the leaders of the gang. He was convicted and sentenced to 25 years in prison.
This turned out to be his lucky break as a vigilante group formed in Jackson County to stop the criminals. On three separate occasions, vigilantes captured members of the Reno Gang who were already in police custody and lynched them. All ten robbers except for John Reno died this way in 1868. Six of them were hanged from the same tree in a place which became known as Hangman Crossing, Indiana.
2. Marm Mandelbaum
Fredericka Mandelbaum (she’s the looker with the fan on the far right) rose through the ranks of New York City’s criminal underground during the mid-to-late 19th century to become the “Queen of Fences,” a shadowy figure who built an empire on stolen goods.
By the 1880s, the New York District Attorney decided it was finally time to take down “Marm” Mandelbaum. There was just one problem, though. By then, she had so many connections that it was impossible to conduct a sting operation using the police without her hearing about it. That’s why he turned to the Pinkertons.
A detective named Gustave Frank was the one to infiltrate Marm’s operation. He posed as a shady silk dealer and secured an introduction with Mandelbaum. She was extremely cautious about working with new people, but Frank played his role very well. He learned everything there was to know about the silk trade and showed himself to be very adept at dealing with the commodity. Eventually, Mandelbaum agreed to do business with him. This led to a raid on her house where police recovered numerous stolen goods. Marm jumped bail and fled to Canada, where she spent the rest of her life.
1. H. H. Holmes
H. H. Holmes was a notorious serial killer who gained infamy for allegedly luring unsuspecting out-of-town victims attending the 1893 World’s Fair in Chicago to his hotel later dubbed “the Murder Castle.” Besides this, he was also an unrelenting con man who always had a scheme in play. It was, in fact, an insurance fraud attempt that first brought him to the attention of Pinkerton detectives.
In 1894, Holmes enlisted the help of an associate named Benjamin Pitezel. The goal was to take out a life insurance policy on Pitezel, fake his death and then cash out. This required a corpse which resembled him, but Holmes took a different course of action. Instead of replacing Pitezel, he simply murdered his cohort.
Pitezel’s wife Carrie was aware of the scam and was convinced by Holmes that her husband was traveling to avoid suspicion. She even allowed three of her children to go with him as she thought Holmes was taking them to see their father.
Meanwhile, the insurance company received a tip about the scheme and hired the Pinkertons. Initially, they investigated the fraud, but became convinced that the dead man was actually Pitezel and that Holmes had killed him. Detectives tracked down the murderer and arrested him in Boston on November 17, 1894. However, the children weren’t with him.
Detective Frank Geyer retraced the movements of Holmes in an effort to locate the missing kids. He found the remains of Alice and Nellie Pitezel in Toronto while their brother, Howard, was killed and disposed of in Irvington, Indianapolis.