by Chris Enss
Aside from women hired specifically as police matrons, widows of slain police officers were sometimes given honorary positions within the department. Titles given to widows meant little at the time; it was, however, the first hint of what would eventually lead to official positions for sworn-in policewomen.5
Even with their limited duties, police matrons in the mid- to late 1800s suffered a barrage of negative publicity. Most of the commentary scoffed at the women’s infiltration into the field. The press approached stories about police matrons and other women trying to force their way into the trade as “confused or cute,” rather than a useful addition to the law enforcement community.6
Allan Pinkerton’s decision to hire a female operative was all the more courageous given the public’s perception of women as law enforcement agents. Kate Warne had the foresight to know that she could be especially helpful in cases where male operatives needed to collect evidence from female suspects. She quickly proved to be a valuable asset, and Pinkerton hoped Hattie Lewis, also known as Hattie Lawton, would be just as effective.7 Hired in 1860, not only was Hattie the second woman employed at the world-famous detective agency, but some historians speculate she was also the first mixed-race woman as well.8
Pinkerton was an exceptional man, looking beyond gender and race as few did at the time. In the late 1840s, he was active in the Underground Railroad, helping many runaway slaves escape to Canada. He spoke out against the Fugitive Slave Act passed by the US Congress in September 1850. The law penalized officials who did not arrest an alleged runaway slave, and subjected them to a fine of $1,000 for aiding any fugitive in his or her efforts to be free. Since any suspected slave was not eligible for a trial, the law resulted in the kidnapping and conscription of free blacks into slavery, as suspected fugitive slaves had no rights in court and could not defend themselves against accusations.9
Chicago became a clearinghouse for runaway slaves. In rural areas such as Dundee, where Pinkerton resided, some enterprising young men were forming businesses to hunt fugitive slaves for a reward. Pinkerton was outraged by the “bloodhounds,” and sought ways to defy them. In 1857, he was one of a delegation called to investigate a slave catcher passing through town. Historians believe it was during this investigation that he met Hattie Lawton. Some of Hattie’s family was suspected of being among a party of slaves Pinkerton was sheltering as they prepared to disperse to Canada.10
Born in 1837, Pinkerton described the widowed Hattie as “delicate and driven.” He wrote that “her complexion was fresh and rose-like in the morning. Her hair fell in flowing tresses. She appeared careless and entirely at ease, but a close observer would have noticed a compression of the small lips, and a fixedness in the sparkling eyes that told of a purpose to be accomplished.”11
Hattie played a key role at the detective agency for many years, assuming various identities and ferreting out information that aided in solving numerous cases. One of the most dangerous assignments in which Hattie participated involved gathering intelligence about Confederate Army movements. In 1862, Hattie and Pinkerton operative Timothy Webster were dispatched to Richmond, Virginia, posing as a wealthy married couple.12
Allan Pinkerton was working with General George B. McClellan, who was general in chief of the Union Army. Pinkerton would become the officer’s personal secret operative. General McClellan received orders from the president at the White House, and he passed them along to Pinkerton, who passed them on to the operatives in the field. Hattie and Timothy pretended to be Rebel sympathizers from Perrymansville, Maryland. Timothy had indeed been in Perrymansville, working to expose a suspected plot by malcontents to damage railroad property. Then, all of the sudden, the situation became of national importance, and for a time Pinkerton and Timothy were part of history in the making.13
Just prior to relocating to Virginia, Timothy had been living in Baltimore and working on cases for the detective agency. His primary objective was to gain acceptance from groups of Southern sympathizers in the area and find out their plans to thwart the Union’s military efforts. After several months, Timothy managed to infiltrate a secessionist group known as the Sons of Liberty. The Sons of Liberty was an underground organization determined to help overtake the government, and Timothy became one of their most trusted members. Confederate secretary of war Judah P. Benjamin recruited him to be a courier for the Confederates’ “secret line” between Washington, Baltimore, and Richmond. The Pinkerton operative ensured that the documents he was carrying made it not only to Rebel combatants, but also to Union officers and Pinkerton staff members. His relationship with the Sons of Liberty was to continue after he relocated.
Unfortunately, the detective fell prey to inflammatory rheumatism and was unable to deliver messages to and from Confederate spies. Daily reports to Pinkerton had stopped as well. Fortunately for the detective agency, another operative was ready to take over Timothy’s duties.14
Hattie Lawton and Timothy Webster were living at the Monument Hotel in Richmond, Virginia, when he became sick. The numerous trips Timothy made across the Potomac River in frigid weather to transport secret documents back and forth brought on his illness. He was confined to bed, and Hattie was by his side to nurse him. She did not have the relationships he did to carry on with his responsibilities as a courier, but she was determined to find her own way to gain secrets.15
Hattie was well acquainted with Confederate secretary of war Benjamin and many members of his staff. They would tip their hats to her on the street and ask about her husband. She believed she could acquire information from one or all of the war cabinet in a social setting; perhaps at a dinner the men might discuss details between one another that could be overheard.16
In late February 1862, Hattie recruited the help of a Pinkerton operative living in Washington named John Scobell. John had been working for the detective agency since the fall of 1861. He was a former slave in Mississippi who had been well educated by his owner, a Scotsman, who had freed him. According to the Central Intelligence archives, he was quick-witted and an accomplished role player, allowing him to function in several different capacities on various missions, including as a cook, laborer, and a musician. He often worked with Pinkerton agents, sometimes playing the role of a servant who attended to horses.
Hattie wanted John to pose as the Websters’ servant and eavesdrop on influential Southern contacts when she and Timothy socialized. In between such engagements, John planned to visit popular taverns in the area to sing and pass the hat. He hoped he might pick up information from Southerners in these settings. After two weeks he learned that Confederate general Joseph E. Johnston was escorting three regiments of Rebel soldiers to Yorktown.17
“Good God!” Hattie remarked when John shared the news. “That means a whole army corps is moving, at least twenty thousand men.” John drafted a report to Pinkerton, and Hattie hurried to tell her superior, Kate Warne, also in Richmond at the time, what had been revealed.18
In the weeks that followed, John and Hattie rode out to the Confederate fortifications surrounding Richmond nearly every afternoon. She was welcomed everywhere. “A pretty young woman was always a cheering sight for battle-fatigued soldiers,” Pinkerton noted in his own report about the matter years later. While Hattie chatted with officers, John, unnoticed, would inventory everything in sight and sketch the entrenchments at will. His daily reports were lengthy. More and more, Hattie was serving as a distraction while John performed the real espionage.19
The majority of orders the spies received from Pinkerton in Washington were addressed to both Hattie and John, but on occasion a message would come through solely for John to read. Those messages would be stuffed into the barrel of a revolver. Not long after the pair had sent word to Pinkerton about Rebel troop movements, a message was delivered to John concealed in a gun. The coded message John deciphered read: “McClellan ready to move. No time for sending reports through here. Daily reports must go directly to McClel
lan. Find a way through lines so Mrs. Lawton can hand reports to Captain Lawton. Extremely important and dangerous. Always be armed. You must protect Mrs. Lawton at any cost. Pinkerton.”20
The following morning John told Hattie about Pinkerton’s message. When night fell, the operatives rode out into the country. Outside Richmond, they waited until the sun rose the next day before pressing on. Hattie had a pass to ride through the lines by day, but the pass was not good in the evenings. They had been instructed by Pinkerton to meet Captain Lawton at an intersection in front of a church. Both knew the location, and at the appointed time the three converged at the rendezvous point.
The first meeting was brief, as Captain Lawton feared they might be discovered. He asked that Hattie and John meet him at an inn in Glendale, farther away from their initial rendezvous site. He believed they could meet there regularly and safely. The inn was run by a woman supposedly loyal to the Union. Daily reports intended for General McClellan and compiled by the spies were hidden in the hollow handle of Hattie’s riding crop. John, acting as her groom (a servant who attends to the horses), rode with a Smith & Wesson tucked inside his shirt. He vowed to protect Hattie, just as Pinkerton had advised.21
During one of the exchanges of reports, John noticed a certain peddler acting suspiciously. The traveling salesman was too loud and overly friendly with the patrons. His backslapping camaraderie was too exaggerated to be sincere. He bought too many drinks for too many people. John shared with Hattie and the captain his concern that the peddler might be a counterspy. The captain left the inn immediately, hoping the cagey man would follow him.22
Sensing their conversation had been compromised, Hattie and John decided they needed to return to McClellan’s headquarters and arrange for transportation back to Washington. Hattie believed if they didn’t return to Pinkerton’s office at the capitol, they risked being arrested by the Rebels and hanged. Timothy continued to struggle with his health, but she and John agreed that his safety, as well as their own, was paramount.23
Just as the spies were about to leave the inn, a stable boy stopped John to let him know that the peddler who had set out after the captain had backtracked and was now waiting down the road with four armed riders. John reasoned the counterspy was guarding against their possible escape to McClellan’s headquarters.24
According to Pinkerton’s account of the spies’ experience as relayed to him in their reports, both were well armed and fully prepared to defend themselves. John stressed to Hattie that their horses were superior to the mounts the peddler and his men had. If they managed to sneak out of the inn, they could ride hard to the nearest Union garrison, twenty miles away. “If we get into trouble,” John reportedly told Hattie, “I’m going to shoot it out, but you keep going. You and Allan Pinkerton are more important than any one man.”25
The pair left the inn through a side door and rode swiftly along at a free and sweeping gallop. Their horses were steady, fast, and sure. They were able to put a great deal of distance between themselves and the inn, and in a short time felt a bit more at ease. “I guess we will get through all right, notwithstanding our fears to the contrary,” Hattie remarked to John. “I don’t know about that,” John replied. “We’re not through with our journey, and there’s plenty of time for trouble yet. Perhaps we had better walk the horses a spell.”26
The pair dismounted and led their rides through a richly cultivated district; on either side were farms whose growing crops had not yet been touched by the ravages of war, and the country, under the soft light of the moon, presented a scene of rare beauty. To the left ran the James River; to the right, the country was broken and hilly. The night was soft and balmy, the silence only broken by the sound of the horses’ hooves as they slowly trotted along. Once the spies felt the horses were sufficiently rested, they climbed back into their saddles and quickly pressed forward to a spot called Wilcox’s Wharf, just beyond which was the Union garrison.27
As the pair approached a growth of timber through which they had to ride, an instinctive feeling of dread came over both of them. “Just the place for an ambush,” Hattie said. “Draw your pistol, John, and be ready in case of an attack.” He did as suggested and urged his horse ahead of Hattie’s. The two made it safely to the edge of the woods, but as they emerged on the other side the peddler and his riders were waiting.
“What to do now was a question to be decided promptly,” Pinkerton later wrote of the incident. “To turn and retreat would certainly ensure their capture . . . so they resolved to bravely continue on their way. A few hurried words were exchanged between them, as they arranged that each should select a man and fire on him the instant they were challenged.”28
As the riders approached, the spies were divided, two going on each side of the road, leaving a space between them. Two of the riders were wearing Confederate uniforms, and two were dressed in civilian clothes. All were heavily armed. The peddler let out a Rebel yell, and Hattie and John spurred their horses into a full gallop. The men hurried after them and in a matter of minutes gradually closed in on the pair. John had his revolver in his hand, but wouldn’t fire on the group until he was sure he would hit one of them.29
The road the spies and counterspies raced down suddenly curved, and the full moon drifted behind the clouds, leaving the pathway in the shadows. John’s horse stepped into a hole, stumbled, and fell. He was thrown unharmed from his mount. Hattie jerked her horse to a stop, turned the animal around, and raced back to the spot where John had hit the ground. He scrambled to his feet and waved to Hattie before she had a chance to climb out of the saddle.
“Are you hurt?” she asked.
“No, but my horse is,” he replied. “Go ahead. Don’t mind me,” he ordered. “Save yourself.” She heard the Rebels yell again and sped off in the direction of the Union camp.30
Listening intently, John could hear the clatter of the hooves of Hattie’s horse in the near distance. Coming closer every instant was the sound of the approaching horsemen. John urged his injured horse to the side of the road and placed himself behind the animal; resting his weapon across the saddle, he waited for the approaching horsemen. The Confederate riders were nearly upon John, who knew he made a good target in the moonlight. When the first rider’s horse was almost on top of him, John took careful aim and fired his gun. The horse went down with a bullet through its head. The rider was knocked unconscious. John shot and killed the second rider. He emptied the remaining rounds into a third Rebel, who uttered a scream of anguish and toppled from the saddle.31
John ducked down to quickly reload his weapon. The remaining man stopped his horse with a jerk that drew the animal back upon his haunches, and then, turning the horse swiftly around, set off in the opposite direction, back toward Richmond. John fired at him as he rode away.32
It wasn’t long before John heard hoofbeats coming from the direction of the path Hattie had taken. In a moment the operative was surrounded by members of the US Cavalry, commanded by Captain Lawton and led by Hattie. John informed the captain that the fourth rider had fled, and a party of four was ordered to track down the renegade. The soldiers soon found the rider lying dead in the bush. The last bullet John had fired had struck the man—who turned out to be the peddler—in the arm, shattering it. The deceased man was taken to the Union lines.33
John was sent to Pinkerton’s headquarters in Washington and reassigned to another case. Hattie returned to Webster’s sickbed to continue caring for him.
It was subsequently learned that the peddler was a Rebel spy who for some time had been visiting the Union camps, gathering information, which he no doubt conveyed to other Confederates. “On his person were found papers which fully confirmed this,” Pinkerton later wrote about the case. “That they failed to reach their destination was a fortunate occurrence for the Union cause.”34
Despite Hattie’s round-the-clock nursing, Timothy Webster’s health continued to decline. He was in constant pa
in, and his joints and muscles were grotesquely swollen. His rheumatism was so far advanced that he had trouble walking and feeding himself. Hattie focused all of her attention on him. Reports to Pinkerton from the two operatives were few and far between. Concerned for the safety of the pair, Pinkerton sent detectives John Scully and Pryce Lewis to investigate.35
The Monument Hotel where Timothy and Hattie were living was a popular hostelry for statesmen, military leaders, and politicians. Spies and counterspies from both the North and South frequented the halls and lobby of the establishment, exchanging secrets and quietly discussing battle plans. Operatives John Scully and Pryce Lewis were unaware that Confederate agents had tailed them from Washington to Richmond. The Pinkerton men were followed to the hotel and to the Websters’ room. As they were leaving, they were recognized by a Rebel soldier, Lieutenant Chase Morton. Scully and Lewis had arrested Lieutenant Morton’s Southern-sympathizing father, Senator Jackson Morton, in late 1861. The lieutenant had the operatives taken into custody and charged with espionage. Neither Timothy nor Hattie was arrested, but a blanket of suspicion covered their every move.36
Scully and Lewis were tried, convicted, and sentenced to be hanged on April 4, 1862. They were granted stays of execution when it was revealed that both men were not American citizens but British subjects. Attorneys for the operatives advised their clients that the order to hang them could be reinstituted if they didn’t cooperate with the Confederate Army and tell all they knew. Pryce Lewis steadfastly refused to give the Rebel leaders any information. John Scully, however, was intimidated into giving up names of double agents, one of whom was Timothy Webster.37
The accusations against Timothy were dismissed at first because he was so well connected with Confederate officials, who didn’t believe Timothy was capable of being a counterspy. Only after Scully had cited examples of Timothy’s duplicity did the Rebel leaders believe the operative was telling the truth. As a result of Scully’s willingness to share, both his and Lewis’s death sentences were commuted. Erroneous information spread that Lewis, as well as Scully, had betrayed Timothy. The error was compounded later when Hattie reported the betrayal as well. Pryce Lewis fought hard to clear his name; the stigma of his betrayal hounded him for most of his life. Neither John Scully nor Pryce Lewis would work for Pinkerton again. In 1911 Lewis ended his life by jumping off the dome of the World Building in New York.38
