The Expressman, Allan Pinkerton, and the Detectives

In late 1858, Allan Pinkerton, founder of Pinkerton’s National Detective Agency (PDNA), received a bulky letter from Edward S. Sanford, vice president of the Adams Express Company containing the case files on the loss of $10,000 from a locked money pouch being transported on a train somewhere between their headquarters in Montgomery, Alabama, and a branch office in Augusta, Georgia in April that year.

Adams had employed at least five detectives to investigate the missing money, and over several months, they amassed no evidence and no real suspects. As a last resort, a New York City Police Inspector told Adams Express Company officials that he knew only one man in the country who possessed the detective ability, vigilance, and dogged perseverance to take up the case and solve it: Allan Pinkerton. 

Sandford listened incredulously and scoffed at the idea of going to Chicago for a detective while New York City was full of them. With his options dwindling in New York, he took the advice and sent the case to Pinkerton.  

At first, Pinkerton glanced through the files and thought to disregard the case altogether. However, as a sense of duty to the friend who recommended him to the Adams Express Company, Pinkerton spent the weekend in his office considering every circumstance of the robbery. Finally, with firm conviction, he drafted a nine-page report to Sanford, stating that he was inclined to blame Nathan Maroney, manager of the Montgomery office. Pinkerton offered no legal evidence from Chicago. Instead, he recommended that Sanford keep Maroney “under strict surveillance before he bites you twice.” 

While there were several people in the chain of custody, Maroney was the only real suspect. Maroney, the son of a doctor from Rome, Georgia, stood as a beacon of professional conduct in his community. With a storied past that included service with the Texas Rangers during the Mexican War, he arrived in Montgomery during the early 1850s.  

When questioned, Maroney said that he knew nothing of the matter. He further stated that he only delivered the packages to the messenger and had a receipt for them. Maroney further stated that he could not be expected to keep track of packages when they were out of his possession. 

When questioned, Maroney said that he knew nothing of the matter. He further stated that he only delivered the packages to the messenger and had a receipt for them. Maroney further stated that he could not be expected to keep track of packages when they were out of his possession. 

Despite the lack of concrete evidence, the mounting suspicions led to a request for Maroney's resignation in January 1859. While he was subsequently arrested, he managed to post bail. A trial date was set for June.  

But then there was another theft — this time it was for $40,000. Sanford sent a new letter to Pinkerton stating, “I have been bit once more.”

The Pinkerton Team: Master Detectives Assemble

Officially on the case, Pinkerton designed an intricate plan for eliciting a confession and finding the money. The thorough investigation took nearly a year and a team of 10 operatives — including Allan Pinkerton himself and other well-known Pinkertons Kate Warne, George H. Bangs, John White, Adam “The Dutchman” Roche, John Fox, De Forest, and the lively, sarcastic, and prim female operative known only as Miss Johnson — most of whom went undercover, working the case from every possible angle. He was sure the perpetrator was Nathan Maroney.  

Pinkerton’s biggest fear was that Maroney’s wife would leave Montgomery with the embezzled money. His fears were realized on a couple of months later when Mrs. Maroney, with her child in tow, embarked on a journey from Charleston to New York via steamer before finding refuge in Jenkintown, a small settlement north of Philadelphia, Pennsylvania, where her sister and brother-in-law lived. 

It was here that Pinkerton brought in Kate Warne, who posed as the wife of Jules Imbert — the notorious French forger who had been caught by the Pinkertons in 1856 — to gain the confidence of Mrs. Maroney and learn where the stolen money was hidden. Miss Johnson was both Mrs. Imbert’s companion and a distraction to the POI while Mrs. Imbert made herself indispensable to Mrs. Maroney. 

Detective De Forest, a man about thirty-five years old, five feet eleven inches in height, remarkably good-looking, with long black hair and a full beard and mustache, was known in Philadelphia a perfect "lady-killer." His job was simply to go to Jenkintown with a carriage and span of horses and romance the suspect’s wife. He knew nothing more of the case.

 

Detective Fox was also undercover in Jenkintown, as a clock and watchmaker — his former trade. His task? Frequenting the town’s bar and befriending the locals to gather intelligence. Very quickly, he became remarkably close to Maroney’s brother-in-law. Drinking buddies, as it were.  

The Fugitive's Trail: Maroney's Road Trip and the Pursuing Shadow

The suspect himself also left Montgomery and led the Dutchman on a long game across months and miles – traveling approximately by boat, train, carriage, and foot. His journey meandered through Chattanooga and Nashville, ultimately leading him to Memphis. It was there that Maroney boarded the "John Walsh" steamer heading for New Orleans, making stops at Natchez and leaving a series of clues before eventually checking into a hotel further downriver. 

When Maroney next appeared, his looks were markedly altered, suggesting he suspected a cloak-and-dagger pursuit. His circuitous route took him to Mobile, then ultimately back to Montgomery, seemingly convinced he had shaken off any followers. What Maroney didn’t realize was that as he changed his appearance, so did the Dutchman.  

Case reports from the Dutchman detailed an extravagant scheme: Maroney used the $10,000 to purchase cotton shares in South Carolina. Maroney placed the $40,000 into a box and sent it via Adams Express delivery to Galveston, Texas, under an alias. The package remained in Galveston until it was forwarded to Natchez. There, Maroney recovered it and secreted it to Montgomery, and subsequently to New York, where Mrs. Maroney retrieved it. Maroney and his wife then took a vacation in Philadelphia. But this is where the story takes a bit of a turn. Maroney was arrested in Philadelphia and sent to a New York jail to await his trial date. 

Enter Detective John White (also known as Julius Wenstrup or J.W. in Agency archives). He had perhaps the most challenging assignment — gaining Maroney’s trust while Maroney was in that New York jail. White played his part well, that of calculated indifference, drawing in Maroney with every fragmented conversation.  

As part of the operation, White was released from jail only after he elicited a confession from Maroney, promising to dispose of the money and help him set up a defense at his trial. Maroney sent a message to his wife to give the money to White. She was hesitant, but ultimately coaxed by her trusted confidante, Mrs. Imbert, she unearthed the money from her sister and brother-in-law’s cellar. White simply went to Jenkintown and picked up the money from Mrs. Maroney.  

Pinkerton and Bangs, who both took turns at going undercover during the operation, brilliantly orchestrated the case. Bangs, Allan’s no. 2 and PDNA’s first general manager, remained in Philadelphia and in communication with the leaders of the Adams Express Company. Nearly the entire amount in its original packaging was returned to the express company. 

Not long after, Maroney was extradited to Montgomery for his trial. He was confident that he would not be convicted, that is, until White walked into the courtroom. Based on J.W.’s testimony and the recovered funds, Maroney was sentenced to ten years of hard labor in the Alabama Penitentiary.  

This was Pinkerton’s first major case in the East, leading to a long-standing relationship with the Adams Express Company (see The Baltimore Plot) and earning more business from other railroad and express companies, banks, jewelers, and other organizations, who now knew that Pinkerton and his team would go to any extreme in the pursuit of justice.