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off to the identity of the customer who had passed the $10 bill, and Pinkerton strolled up to him, pretending to admire his horse. He also took careful note of the stranger: gray hair, gray eyes, about sixty-five years old, gold ring on his left hand. Pinkerton struck up a conversation with him, trying to give the impression of being the kind of guy who might be a useful recruit for a shady operation. The stranger, intrigued, invited Pinkerton for a chat outside town, where no one else could hear it. He said he was John Craig, from Vermont, and he asked about Pinkerton’s background and occupation. Craig thought Pinkerton might make a good pass-through for the dummy money operation, and he offered to give Pinkerton fifty $10 bills in exchange for $125 in real money.

Pinkerton scrambled back to the storekeepers for the cash. He turned it over to Craig, who left the fake bills for him to pick up later under a rock. Now Pinkerton knew that there was a counterfeit ring, and what the going rate was for the bills. But he needed to catch Craig with the bills on his person in order to make an arrest. He set up another deal, for a $4,000 purchase to be made in the lobby of the Sauganash Hotel* in Chicago. At the right instant, Pinkerton made a prearranged signal, and the local Cook County sheriff charged into the room and collared Craig.

Word of the successful undercover operation and arrest landed Pinkerton the job of deputy sheriff of Kane County, where he worked part-time while continuing his barrel-making business. But he wasn’t destined to stay a cooper much longer. In 1847, William Church, the sheriff of Cook County, offered Pinkerton a chance to move to Chicago and become deputy sheriff there. Allan and Joan Pinkerton moved to the bustling young city.

Pinkerton thrived in Chicago. The city was growing at an astonishing rate as thousands of new immigrants from Europe and the East Coast were pushing its city boundaries out into what had once been a rural landscape. In just over three years, Pinkerton became one of the most legendary lawmen in town. In 1849, Mayor Levi Boon appointed him as Chicago’s first—and only—detective. It was a tough world, and law enforcement officers were called to use their fists and boots in the pursuit of a rough sort of street justice that could keep the straining city under some sort of control.

Next, Pinkerton jumped from the police force to a job at the U.S. Post Office, where he worked solving petty crimes as a mail agent. At the post office, he went undercover again, posing as a mail sorter to help nail a postal worker who had absconded with $3,738 in cash stolen from inside letters. The criminal and his brother turned out to be nephews of none other than the postmaster of Chicago himself. When the news hit the papers, Pinkerton was singled out for high praise as the best detective in the country.

Press like that can change a career, and that’s what happened to Pinkerton. In 1850, he quit government service and set up a private agency with a lawyer as his partner. They called it the North-Western Detective Agency and opened a small office at the corner of Washington and Dearborn in downtown Chicago. The business began slowly and had its troubles. For one thing, historians believe that Pinkerton ousted his partner, Edward Rucker, within a year of starting the firm. But over time it became successful, and eventually it became a private intelligence juggernaut. By then, it was renamed Pinkerton’s National Detective Agency. The firm would no longer bill itself as a creature of Chicago—Allan Pinkerton signaled his national ambitions in the letterhead of his company.

In the 1850s, laws were enforced locally, county by county. There was no FBI, and the federal government didn’t have much ability to track criminals from one state to another.* With the sprawling western frontier attracting all sorts of rogues and scoundrels, and improvements to transportation making it possible for them to commit crimes in county after county as they moved west, there was a desperate need for a police force. That