Lincoln's Spymaster: Chapters 7–9

Even though she was living in Washington, D.C., the capital of the Union, Greenhow fiercely supported the newly formed Confederacy. But this wasn’t unusual in Washington, D.C., which was teeming with Southern sympathizers who some called copperheads.

“Instead of loving and worshipping the old flag of the Stars and Stripes, I see in it only the symbol of murder, plunder, oppression, and shame!”

But unlike Pinkerton, whose strategy was to remain anonymous and in the shadows, focusing on the secrecy of the operation, Greenhow wasn’t so discreet. She and her fellow spies bragged and word soon reached the War Department.

“Her image is daguerreotyped on my mind,” said Greenhow. “And as it is an ugly picture, I would willingly obliterate it.”

They looked through every single book, page by page; took apart the furniture and framed paintings; and checked every nook and cranny.

For several months, Greenhow was shown leniency and kept under house arrest.

“I sympathize with any and every person who is deprived of liberty,” Pinkerton wrote in his report to Brigadier General Andrew Porter, Provost-Marshal.

“Webster’s talent in sustaining a role…amounted to positive genius,” said Pinkerton.

Always well-mannered and amicable, Webster discussed politics calmly and with conviction.

Although he had some acquaintances in Baltimore from his time spent in Perrymansville during the Baltimore Plot, within a week he was the leader of a clique—looked up to and highly regarded.

Zigler was the ringleader of a gang of ruffians in Baltimore.

“Hold your distance, you miserable cur,” said Webster.

Soon after, Webster managed to infiltrate the covert Knights of Liberty. The secret organization was planning an attack on Washington, D.C., with an army of ten thousand Confederates.

Brigadier General John Henry Winder was Richmond’s head of military police, or provost marshal, who ran counterintelligence and oversaw the prisoners of war.

Lawton had infiltrated Southern society, posing as a Southern belle, which allowed her to cultivate friendships with prominent people.

“I heard nothing further from him, directly, and for weeks was utterly ignorant of his movements or conditions,” said Pinkerton.

But Pryce Lewis refused.
“It would be folly,” he told Pinkerton.
Lewis wasn’t worried about his ability to find Webster. He was worried someone would recognize him.

“I have good news for you, Lewis,” he said. “President Davis has respited you for two weeks.”
But the priest made it clear that it didn’t mean Lewis wouldn’t hang.

Pinkerton was in the field with McClellan and the army, just south of Richmond, when he learned about the arrests of his operatives. He was reading the Richmond newspaper when he came across the headline: THE CONDEMNED SPIES.

The article, printed on April 5, stated that their executions were to have already taken place. The gallows were built. But Scully’s and Lewis’s executions were postponed.

It is intimated, and we believe on good authority, too, that the condemned have made disclosures affecting…several persons.

Rumor had it yesterday that one of the parties thus implicated was an officer holding a place under the Government.

“I know that too well—I am to die, and I wish to die like a man. I know there is no hope for mercy, but, sir, I beseech you to permit me to be shot, not be hanged like a common felon—anything but that.”

Half-hung, Webster was lying on his back, stunned.
The guards picked him up and carried him back onto the scaffold.

When Pinkerton learned that Timothy Webster was buried in a pauper’s grave in Richmond, it tormented him.

Since March, Pinkerton and his Secret Service had been traveling with McClellan on the front lines and assessing the military strength and movements of the Confederate army.

He and his army had successfully defended Richmond, pushing McClellan and his troops back, had scored a victory at the Second Battle of Bull Run, and had captured the Union garrison at Harper’s Ferry in Virginia.

In preparing his strategy, McClellan’s biggest worry was the number of enemy troops. He didn’t want to be outnumbered. To compensate, McClellan knowingly used inflated numbers so he could request more troops.

If we defeat the army arrayed before us, the rebellion is crushed. For I do not believe they can organize another army.

On the morning of September 16, Pinkerton went on a reconnoitering mission with General McClellan’s cavalry. Pinkerton wanted to see the position of the Confederate troops with his own eyes.

More Confederates streamed out of the surrounding woods and into the cornfield, coming face-to-face with more Union soldiers called in from reserve. Fierce fighting ensued, leaving ten thousand soldiers dead or wounded.

On average, there was a casualty every two seconds. By the end of the day, twenty-three thousand soldiers were dead or wounded.

“The dead are strewn so thickly that as you ride over it you cannot guide your horse’s steps too carefully. Pale and bloody faces are everywhere upturned. They are sad and terrible, but there is nothing which makes one’s heart beat so quickly as the imploring look of sorely wounded men who beckon wearily for help which you cannot stay to give,” George Smalley reported in the New-York Tribune.

Whether to renew the attack on the 18th or to defer, even with the risk of the enemy’s retirement, was the question before me.

After a night of anxious deliberation, and a full and careful survey of the situation and condition of our army, the strength and position of the enemy, I concluded that the success of an attack on the 18th was not certain.

I am aware of the fact that under ordinary circumstances a general is expected to risk a battle if he has a reasonable prospect of success.

Despite all the criticism surrounding McClellan, Pinkerton remained steadfast and true to him.

After severing his ties with the Secret Service and turning his back on espionage, Pinkerton returned to being a detective, working for the War Department in Washington, D.C.

Although Pinkerton had hoped that his younger son, Bob, would stay in school and become a doctor or lawyer, in 1864, sixteen-year-old Bob ran away from Notre Dame and forcefully told his father that he was going to be a detective. Pinkerton conceded, and was training both sons to take part in the dangerous and oftentimes violent family business.

On the same day that Pinkerton found out about the assassination of President Lincoln, the mirrors and chandeliers in the White House were already covered with black cloth. His funeral procession had begun.