After the Upper Canada Rebellion, he boasted that he had partaken in the 1837 Caroline Affair, the sinking of an American steamboat that had been supplying William Lyon Mackenzie's rebels with arms.
Three years later, he was arrested by the United States and charged with the murder of the sailor killed in the attack, but his incarceration infuriated Canada and Great Britain, which demanded his repatriation in the strongest terms; arguing that any action taken against the Caroline had been taken under orders, and the responsibility lay with the Crown, not McLeod himself.
[6] In response to American actions, a British force consisting of Canadian militiamen crossed the Canada-United States border, drove away the crew of Caroline and burnt the vessel.
[6] Described as "a man of gentlemanly bearing and demeanor",[6] McLeod was arrested on November 12, 1840, after visiting Lewiston, New York and boasting that "his sword had drank the blood of two men on board the Caroline" three years earlier.
[7] He was subsequently charged with the murder of Amos Durfee - an African American sailor found dead near the dock after the boat was destroyed,[6] and held in Lockport Jail.
[8] British ambassador Henry Stephen Fox initially informed the Americans that the legal precedent established in handing over a man named "Christie" three years earlier after his arrest for the Caroline burning would also be applied to McLeod.