Confederate Operations in Canada and New York

This is a book by John W. Headley, who was one of the confederate operatives operating out of Canada. He had served under Nathan Bedford Forrest and was a scout for John Hunt Morgan. He was involved in plots to free confederate prisoners held at Johnson’s Island and was involved in the fire attack on New York City. He published his reminiscences in 1906, and you can download and read the book for free here or here.

This is a pretty good book. Headley starts out by telling us what started the war. “The sectional animosities engendered by the agitation in the Northern States for the abolition of African slavery reached a climax upon the election of Abraham Lincoln to the Presidency of the United States in November, 1860. The Southern people construed this event to mean the freedom of their negroes. Indeed, the passions of the triumphant party in the Northern States and their purposes were no longer concealed.” [p. 19]

Headley relies a great deal on the Official Records, reproducing a large number of dispatches in his book. He doesn’t give us pictures of Forrest the man or Morgan the man. His account is basically what he did along with general accounts of what happened at various points in the war. The strength of the book is when he tells us about the plotting and actions in Canada and New York. He gives us an idea of the treason some high profile Democrats engaged in: “On the 9th of June Captain Hines had been sent to confer with Mr. Clement L. Vallandigham, then at Windsor, Canada, in order to obtain such information on that subject as that gentleman could furnish. On the 9th of June Mr. Thompson himself met Mr. Vallandigham, and the two thoroughly discussed the existing disaffection, which had already crystallized into the semimilitary organization popularly known as the ‘Sons of Liberty.’ Mr. Vallandigham was the Grand Commander of this order, and he represented that it was in all three hundred thousand strong. There were eighty-five thousand members, he said, in Illinois, fifty thousand in Indiana, and forty thousand in Ohio. As early as January, 1861, Hon. Fernando Wood, then mayor of New York City, addressed a message to the Common Council, in which he recommended that New York should secede and constitute herself a free city, and formulated the idea, then so prevalent, in very striking terms : ‘It may be said that secession or revolution in any of the United States would be subversive of all Federal authority, and, so far as the central government is concerned, the resolving of the community into its original elements—that, if part of the States form new combinations and governments, other States may do the same. California and her sisters of the Pacific will no doubt set up an independent republic, and husband their own rich mineral resources. The Western States, equally rich in cereals and other agricultural products, will probably do the same. Amid the gloom which the present and prospective condition of things must cast over the country. New York, as a Free City, may shed the only light and hope of a future reconstruction of our blessed Confederacy.’ Mr. Thompson, of course, and the Confederates acting under his directions, would have preferred to see the whole tendency of the movement directed toward the establishment of a separate confederacy of Northwestern States. So far as possible, they encouraged this idea among the parties who seemed most sensible of the stimulus of personal ambition. At this time Mr. Vallandigham introduced to Mr. Thompson a prominent official of the order who occupied somewhat the position of its adjutant-general, thoroughly indorsing his reliability and energy. Through this gentleman Mr. Thompson subsequently arranged for the distribution of funds to be used in arming and mobilizing the county organizations. Conferences with very many Northern men who at that period visited Canada, who were not connected with the order of the ‘Sons of Liberty,’ nor informed in any wise of the purposes of the Commissioners, further developed the fact that there was a widely spread feeling of fatigue, to use the mildest term, with the war and those who were profiting by it. A subsequent investigation of the character and sentiment of the ‘Sons of Liberty’ confirmed perfectly all that Mr. Vallandigham had said, and revealed a feverish desire of the general membership to assert and maintain their rights. Mr. Lincoln’s call, about this time, for five hundred thousand more men for the army, and the proposed draft to provide them, intensified the wish to resist a further prosecution of the war, and seemed to have ripened it into resolve. Mr. Thompson became thoroughly convinced that the movement could be induced, and that it would be successful. But there was always the doubt whether men bound together merely by political affiliations and oaths, behind which there was no real legal authority, could be handled like an army. Mr. Vallandigham returned to Ohio about the middle of June. He made speeches immediately, which seemed intended to invite his rearrest and the action he had predicted. In his first speech, after his return, at Hamilton, he almost declared the existence and purposes of the order. He said: ‘But I warn also the men in power that there is a vast multitude, a host whom they cannot number, bound together by the strongest and holiest ties, to defend, by whatever means the exigencies of the times shall demand, their natural and constitutional rights as freemen, at all hazards and to the last extremity.’ The 20th of July seemed to have been determined upon as the date of outspoken declaration of resistance. The inclination to prevent the enforcement of the draft pervaded all classes who would probably be subjected to it, and might unite all such men in an effort to prevent it. It was understood that a simultaneous movement would be concerted in Illinois and Indiana, and that in each of those States the State officers would be practically deposed and provisional governments organized. In his first report to Richmond, made in July, Mr. Thompson said: ‘Though intending this a Western confederacy and demanding peace, if peace be not granted, then it shall be war. There are some choice spirits enlisted in this enterprise, and all that is needed for success is unflinching nerve. For our part, it is agreed that Capt. T. Henry Hines shall command at Chicago, and Capt. John B. Castleman at Rock Island. If a movement could he made by our troops into Kentucky and Missouri, it would greatly facilitate matters in the West. The organized forces of the Federal Government would thus be employed, and this would give courage and hope to the Northwestern people. The rank and file are weary of the war, but the violent abolitionists, preachers, contractors, and political press are clamorous for its continuance. If Lee can hold his own in front of Richmond, and Johnston defeat Sherman in Georgia prior to the election, it seems probable that Lincoln will be defeated. Nothing less, however, can accomplish this end. It is not improbable that McClellan will be nominated by the war Democrats. His recent war speeches have broken him down with the peace party, but in my opinion no peace candidate can be elected unless disaster attend the Federal armies in Virginia and Georgia. In short, nothing but violence can terminate the war.’ ” [pp. 222-224]

Headley details a number of plans including a plan to take control of Union vessels on Lake Erie and free confederates imprisoned on Johnson’s Island in order to disrupt things in the North. “Captain Cole had located at the West House, in Sandusky, and hailed from Philadelphia. After Cole and Beall had agreed upon the plan to capture the Michigan, Beall departed to carry out his part of the undertaking. The plan provided that Beall with a force of twenty Confederates should take passage on the steamer Philo Parsons, at or below Detroit, put the passengers and crew ashore, and then steam ahead in the usual way as if going to Sandusky until near the Michigan, when they would turn and run alongside, board and capture the gunboat. The prisoners on Johnson’s Island would then be released.” [p. 234] The plan went awry when someone informed the authorities of the plot and the Captain Cole involved in the plot was arrested.

He talks about the raid on St. Albans, Vermont as well as the failed conspiracy to disrupt the 1864 presidential election, which itself was disrupted when Benjamin Butler was sent to New York with troops to keep the peace. “The leaders in our conspiracy were at once demoralized by this sudden advent of General Butler and his troops. They felt that he must be aware of their purposes and many of them began to fear arrest, while others were defiant. Among the latter were Mr. Horton of the Day Book, Mr. Brooks of the Express, and many others. However, Mr. McMasters sent for us and expressed his fears that our plans could not be carried to consummation. He appeared anxious to stem the effects of the arrival of troops but said we could not afford to make a failure. The next day, November 7th, he reported that at a conference of the leaders it was decided to postpone action. … We could do nothing but acquiesce in the views of the New York management. However, we were assured that the delay was only temporary, and it was contended that after the election, if all passed off quietly, then the troops would depart. But to increase the existing fears of our friends, the papers, on the morning before the election and also the next morning, announced the arrest of a number of our friends at Chicago and of a number of the leaders in Chicago of the ‘Sons of Liberty,’ who were to cooperate with Hines and his men. It looked as if that expedition had failed already. … We watched General Butler daily, hoping for his departure, but it began to look as if he and his troops had come to stay. The next morning after the election we saw from the papers that nothing had occurred in any other city. We presumed that the same difficulties had existed in all the cities. Our New York friends were still unable to agree upon an auspicious day for action. … But the more we insisted on the attempt in New York the weaker Mr. McMasters became. Captain Longmire was equally anxious with us to make the attempt at all hazards. We tried to get an agreement for Thanksgiving Day, but Butler still occupied the city and our cause had not gained headway in the Confederacy. Finally, after repeated interviews Mr. McMasters decided to withdraw from any further connection with the proposed revolution when it was foredoomed to failure. This left us practically at sea.” [pp. 270-271]

The failure of that plot led directly to the plan to burn New York City’s business district. “The duty of going after the Greek fire was considered rather a dangerous mission under the circumstances, but I was selected to go. I found the place was in a basement on the west side of Washington Place. The heavy-built old man I met wore a long beard all over his face. All I had to do was to tell him that Captain Longmire had sent me for his valise. He handed it over the counter to me without saying a word. I turned and departed with the same silence. The leather valise was about two and a half feet long and heavy. I had to change hands every ten steps to carry it. No carriage was in sight. I had not expected the valise to be so heavy. But I reached the City Hall Square with it safely and boarded a street car which started there for Central Park, going up Bowery street. The car was crowded and I had to put the valise in front of me on the floor in the passway, as the seats ran full length on each side of the car. I soon began to smell a peculiar odor—a little like rotten eggs—and I noticed the passengers were conscious of the same presence. But I sat unconcerned until my getting off place was reached, when I took up the valise and went out. I heard a passenger say as I alighted, ‘There must be something dead in that valise.’ When I lugged it into our cottage the boys were waiting and glad of my safe return. I was given the key with the valise and opened it at once with some curiosity to investigate the contents. None of the party knew anything about Greek fire, except that the moment it was exposed to the air it would blaze and burn everything it touched. We found it to be a liquid resembling water. It was put up in four-ounce bottles securely sealed. There were twelve dozen bottles in the valise. We were now ready to create a sensation in New York. It had been agreed that our fires would be started in the hotels, so as to do the greatest damage in the business district on Broadway. The eight members of our party had each taken a room at three or four hotels. In doing this we would buy a black glazed satchel for $1.oo and put an overcoat in it for baggage. The room at each hotel was used enough to show that it was being occupied. In leaving, of course the overcoat would be worn and the satchel left behind empty. It was agreed that our operations should begin promptly at 8 o’clock p. m., so that the guests of hotels might all escape, as we did not want to destroy any lives.” [pp. 272-273] This plan also failed, as all the fires they managed to start were put out very easily.

In summing up the lack of accomplishment of the confederate plotting from Canada, Headley tells us, “The ill-fated expedition to Buffalo and Dunkirk ended the active operations against the enemy by the ‘Raiders from Canada.’ The most of the Confederates began to depart for the South upon the advice of Colonel Thompson. None of us had ever been paid any wages in Canada. In fact, none were due except in Confederate money when we returned to the Confederacy. Colonel Thompson furnished money for expenses only in Canada and for the journey south. All the negotiations for peace which had been entered into between Thompson, Clay, Holcomb and Sanders, of the South, and Greeley, Black, and others, for the North, had failed. All the efforts of Confederates at Chicago, under Hines and Castleman, which promised so much, had failed. The plan of Cole and Beall to capture the gunboat Michigan, which would have given the mastery of the Lakes to the Confederates, had failed. The mission of the Confederates to New York City under Martin had failed. The success of either of these undertakings it was believed would have ended the war. … Now many of our best men were in prison. Burley at Toronto. Cole at Sandusky. Young and his comrades at Montreal. Beall and Anderson in New York City. Grenfel, Shenks, Marmaduke, Cantrill and Travers at Chicago, besides Walsh and Morris of the ‘Sons of Liberty,’ at Chicago; and Horton, McDonald, and others in New York.” [pp. 308-309]

This book is a very good narrative of the plotting the confederates engaged in, including plotting with Democrats from the loyal states. It also tells us the outcomes of the plots. I can recommend this highly for those interested in confederate secret operations.

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