Covert Operations


Included here:

1. Dissent and Treason in the North

2. Operations from Canada

a. Northwest Conspiracy

b. St. Albans Raid

c. Burning New York

d. Alexander Keith, Jr.


1. Dissent & Treason in the North

Abzug, Robert H. "The Copperheads: Historical Approaches to Civil War Dissent in the Midwest." Indiana Magazine of History 66, no. 1 (1970): 40-55.

Ayer, I. Winslow. The Great Treason Plot in the North during the War. Chicago: U.S. Publishing, 1895. [Petersen]

Curry, Richard O. "The Union as It Was: A Critique of Recent Interpretations of the 'Copperheads.'" Civil War History 13 (1967): 25-39.

Donnelly, Ralph W. "District of Columbia Confederates." Military Affairs 23 (Winter 1959-1960). [Petersen]

Fesler, Mayo. "Secret Political Societies in the North during the Civil War." Indiana Magazine of History 14 (1918): 183-286.

Milton, George Fort. Abraham Lincoln and the Fifth Column. Washington, DC: Infantry Journal, 1943. []

Rehnquist, William H. [Chief Justice of the United States] "The Milligan Decision." MHQ: The Quarterly Journal of Military History 11, no. 2 (Winter 1999): 44-49.

This is an excerpt from the Chief Justice's book, All the Laws But One (New York: Knopf, 1998), with a context-setting "Editor's Note." Lambdin P. Milligan was an Indiana Sons of Liberty leader who, with others, was found guilty under President Lincoln's martial laws and sentenced to hang. On 3 April 1866, the U.S. Supreme Court ordered Milligan and the others freed because the military commission which tried them lacked jurisdiction. Rehnquist concludes that "[t]he Milligan decision is justly celebrated for its rejection of the government's position that the Bill of Rights has no application in wartime."

Smith, Bethania Meradith. "Civil War Subversives." Journal of the Illinois State Historical Society 45 (1952): 220-240.

Treadway, Gilbert R. Democratic Opposition to the Lincoln Administration in Indiana. Indianapolis: Indiana Historical Bureau, 1973.

[Vallandigham, Clement L.] The Record of Hon. C.L. Vallandigham on Abolition, the Union, and the Civil War. Columbus, OH: Walter, 1863.

This is a collection of the speeches and writings of the best known of Ohio's Copperheads; they do not address intelligence issues.

Vallandigham, Edward N. "Clement L. Vallandigham -- Copperhead." Putnam's Monthly 2 (1907): 590-599.

Weber, Jennifer L. Copperheads: The Rise and Fall of Lincoln's Opponents in the North. New York: Oxford University Press, 2007.

Tyler, Civil War Book Review [], says this work "is extremely well written" in "engaging prose"; and the author "never overloads the reader with superfluous facts or details, as do so many books that developed from doctoral dissertations." Nonetheless, "Weber's study ultimately leaves the reader disappointed. Part of the problem is that Weber never clearly defines what a Copperhead is," sweeping multiple forms of dissent into her work. Thus, the book is "particularly weak in analyzing the motivations of her subjects." In addition, it "lacks sufficient detail on many of the key events in the Copperhead story."

Wubben, H.H. "The Maintenance of Internal Security in Iowa, 1861-1865." Civil War History 10, no. 4 (Dec. 1964): 401-415.

Security concerns to state officials included the southern border countries with Missouri and the state's vocal Copperhead minority. "Iowa's officialdom and its loyalist citizens consistently exaggerated both threats."


2. Operations from Canada

a. Northwest Conspiracy

Bovey, Wilfrid. "Confederate Agents in Canada during the American Civil War." Canadian Historical Review 2 (Mar. 1921): 46-57.

Andrews, Corbin. "Johnny Canuck's Influence on the [Confederate] Rebels." National Post (Toronto), 24 Mer. 1999, A17.

According to Casis Intelligence Newsletter 34 (Winter 1999), this article concerns some studies done in Guelph (south of Toronto) on the association between local ironmonger Adam Robertson and Confederate agents plotting to free Confederate prisoners being held at Johnson's Island, Ohio.

Headley, John William. Confederate Operations in Canada and New York. New York: Neale, 1906. [Reprinted] Alexandria, VA: Time-Life Books, 1984.

Headley served under both Nathan Bedford Forrest and John Hunt Morgan but is best known for his participation in the "Northwest Conspiracy." He was involved in the November 1864 attempt to burn part of New York City and in a January 1865 effort to kidnap Vice President-elect Andrew Johnson.

Horan, James D. Confederate Agent: A Discovery in History. New York: Crown, 1954.

Thomas Henry Hines led Buckner's Guides, served with Morgan's Raiders, and organized intelligence and sabotage networks among the Copperheads, as the northern anti-war Democrats were called. He was captured in Ohio in July 1863 during Morgan's abortive raid, but escaped in November. In April 1864, he set up headquarters in Toronto, Canada, as the military commander of the Northwest Conspiracy.

Kinchen, Oscar A. Confederate Operations in Canada and the North: A Little-Known Phase of the American Civil War. North Quincy, MA: Christopher, 1970.

Starr, Stephen Z. Colonel Grenfell's Wars. Baton Rouge: Louisiana State University Press, 1971.

George St. Leger Grenfell was a classic 19th century British soldier of fortune who joined Gen. John Hunt Morgan in 1862. Recruited to participate in the "Northwest Conspiracy" in 1864, his planned attack on Camp Douglas near Chicago was betrayed. Grenfell was captured, tried, and sentenced to death. His sentence was commuted, and he was sent to Fort Jefferson in the Dry Tortugas. It is assumed that he died in an escape attempt in March 1868. O'Toole, Encyclopedia, p. 210.

Starr, Stephen Z. "Was There a Northwest Conspiracy?" Filson Club History Quarterly 38 (1964): 323-341.


b. St. Albans Raid

On 19 October 1864, a group of about 30 Confederate raiders attacked the town of St. Albans, Vermont. They succeeded in robbing the town's banks and terrorizing the citizens, but failed in their objective of burning the town. The raiders fled back into Canada where some were captured by the Canadian authorities. Extradition to the United States was denied by the Canadian government, and the men were eventually released. John William Headley, Confederate Operations in Canada and New York (New York: Neale, 1906; and Alexandria, VA: Time-Life Books, 1984), has a brief account of the raid which is reproduced in part in Philip Van Doren Stern, Secret Missions of the Civil War: First-Hand Accounts by Men and Women Who Risked Their Lives in Underground Activities for the North and South (Chicago: Rand MacNally. 1959; and Avenel, NJ: Wings Books, 1990).

Benjamin, L.N., comp. The St. Albans Raid: or, Investigation into the Charges. Montreal: John Lovell, 1865. [Petersen]

Branch, John, Sr., comp. St. Albans Raid. St. Albans, VT: John Branch Sr., 1935. [Petersen]


c. Burning New York

Brandt, Nat. The Man Who Tried to Burn New York. New York: Berkley, 1990.

Surveillant 1.3: A "band of renegade Confederate soldiers, led by Robert Cobb Kennedy ... tried to burn New York City."

Headley, John William. Confederate Operations in Canada and New York. New York: Neale, 1906. [Reprinted] Alexandria, VA: Time-Life Books, 1984.

Headley served under both Nathan Bedford Forrest and John Hunt Morgan but is best known for his participation in the "Northwest Conspiracy." He was involved in the November 1864 attempt to burn part of New York City and in a January 1865 effort to kidnap Vice President-elect Andrew Johnson.

Scott, Phil. "1864 Attack on New York." American History, Jan. 2002. []

On 25 November 1864, Confederate agents tried "to set New York City aflame." The plot was put together by Robert Martin. He and seven other Confederate agents, including his second-in-command John W. Headley, made their way from Canada to New York City. The saboteurs set fires in more than a dozen buildings, but all of the fires were extinguished without major damage. The eight arsonists made their way back to safety in Canada. Later, one of them, Robert Cobb Kennedy, was captured in Detroit, transported back to New York, tried, and hanged.

Thompson, J. A Leaf from History: Report of J. Thompson, Secret Agent of the Late Confederate Government, Stationed in Canada, for the Purpose of Organizing Insurrection in the Northern States and Burning Their Principal Cities. Washington, DC: Office of the Great Republic, 1868. []

d. Alexander Keith, Jr.

Larabee, Ann. Dynamite Fiend: The Chilling Tale of a Confederate Spy, Con Artist, and Mass Murderer. New York: Palgrave Macmillan, 2005.

According to the author, this work "concerns one of the most infamous Confedertae spies in Canada, Alexander Keith, Jr.... It sheds new light on spies and spy rings during the war."

A Publishers Weekly review (via says that although "parts of this story, especially its climax [the bombing of a German ship in 1875], have been well documented, Keith's aliases kept investigators from connecting all the dots. Larabee does so in this book, but while her historical sleuthing is extensive, she often embellishes on characters' supposed thoughts and feelings in a way that will frustrate readers wanting a more rigorous account."

Taylor, Booklist (via, calls this "an engrossing narrative." During the Civil War, Keith "posed in Halifax as a sympathizer and agent for Confederate blockade runners; in reality, he ripped them off.... Detailed but never dull, Larabee's account ... [is] a high-quality historical addition to the true-crime genre."

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