• Choose a category
• All
• Classic-Fiction

Thompson and Hines would not be put off, however, and managed to pry out of the Sons of Liberty a new date for the uprising. It would now take place on August 29 in Chicago during the Democratic National Convention. The obvious wavering of the Sons of Liberty made the Confederates anxious, but they reckoned that even if only half the promised five thousand members actually came, there would still be a reasonable chance of success. Hines sent out the long-awaited signal for his followers to convene in Toronto. On August 24 Thompson handed Hines his written orders and $24,000 to cover the expenses of the mission. Over the next few days, Grenfell and sixty others slipped into Toronto. Each man was provided with $100 in cash, a pistol, ammunition, and a return train ticket to Chicago. Hines outlined the plan: they were to travel inconspicuously, in groups not larger than three or four. Once in Chicago they would meet at the Richmond House hotel for the rendezvous with the Sons of Liberty. One force would make for Camp Douglas to liberate its 5,500 inmates. The other would travel two hundred miles west to Rock Island Barracks to release its 9,000 Confederate prisoners.

Grenfell left with Hines and a couple of others on August 26. He chose as his costume for the occasion a gray hunting suit, in the same hue as the Confederate uniform, two sporting guns, and a yellow-spotted hunting dog—a loud disguise entirely characteristic of him. When one of Grenfell’s traveling companions pointed out that the suit would probably cause him to be arrested the minute he stepped off the train, he replied: “I have my English papers, and my gun and my dog, and if they ask me what I am doing, I will say I am going hunting.”36 The party reached Chicago on August 28 and proceeded straight to Richmond House. Grenfell signed the register under his own name. Hines, on the other hand, kept to his alias of Hunter. The Confederates had a suite of rooms—all labeled “Missouri Delegation”—which was deemed a sufficient disguise to allow them to blend in with the thousands of real delegates who were crowded four to a room in the city’s overburdened hotels. (The plumbing, which had so irritated Anthony Trollope during his stay in the city, remained unimproved.)

That night, the Confederates and Sons of Liberty met for the first time since the secret conferences in Canada. They revealed “that something had gone wrong”: no orders had been sent to the forty thousand members in Ohio or the fifty thousand in Indiana. By way of exculpation they pointed out that the mission had already been exposed in several newspapers and that Camp Douglas had received additional Federal troops.37 The Confederates were incensed. It seemed impossible that the hundreds of thousands of dollars funneled to the Sons of Liberty would fail to produce a single fighter. Outside the hotel windows the city was heaving with antiwar protesters, many of them obviously wearing sidearms. At least some of them, Hines insisted, would be eager to see a little action.

The embarrassed conspirators agreed to supply the Confederates with five hundred men by the following evening. The Camp Douglas plan would be abandoned, and the less guarded prison at Rock Island would become the sole target. Under the new plan, one of Hines’s deputies, John Castleman, and twenty Confederates would accompany the Sons of Liberty, while Hines and the remaining fifty would provide support by cutting the telegraph wires and stopping all trains in and out of Chicago. With the help of the prisoners from Rock Island Barracks, they would commandeer the trains and head two hundred miles south to Springfield, the state capital. In a few hours, Illinois would be theirs.

The Confederates waited uneasily for the sun to set. Outside, excited crowds tramped to and from the convention hall. Vallandigham avoided Richmond House: he was far too busy squeezing and working the delegate system. Prison breaks and political assassinations could not have been further from his mind. Only Charles Walsh,