The Montreal spy ring was a spy ring of the Spanish Empire that operated in Montreal, Quebec during the Spanish–American War commanded by Ramón de Carranza y Fernández Reguera and Juan Dubosc. Its intention was to collect intelligence on the United States. The ring briefly operated out of the Windsor Hotel before being forced to relocate to a house on Tupper Street. Despite the fact that this spy ring only briefly existed, it had an outsized impact on the intelligence field and espionage. George A. Downing, a member of the ring, was the first spy recruited from within the Department of the Navy to spy on the United States. However, he was never tried; two days after he was apprehended, he was found hanging from the bars of his prison cell's window. The Montreal spy ring was broken mostly by an emergency "special force" of the Secret Service under the command of John Wilkie. The spy ring was only broken, however, with the assistance of the Canadian government and the US diplomatic corps. This case also built the early career of Secret Service agent William J. Burns, who would later become the director of the FBI. Although this success was widely celebrated in the press at the time, it also masked the controversial nature of the force's methods, which included detentions without trial, unauthorized searches, interference with private correspondence, and the selective leaking of sensitive information for political purposes.
Origins during the Cuban War of Independence
Spanish legation at Washington, D.C.
The central figure in the Montreal spy ring was Ramón de Carranza, a lieutenant in the Spanish Navy. Carranza, then in his mid-thirties, was a career naval officer known for his skill with both sword and pistol. Before his period of diplomatic service, he had commanded a gunboat in Spanish Cuba. In 1896, during Cuban War of Independence, Carranza had also led several landing assaults against Cuban insurrectionists. In the Spanish naval operation at Río de San Juan on October 15, 1896, surrounded on all sides and outnumbered, he performed actions which earned him two Crosses of Military Merit and the Military Naval Order of Maria Christina.
In March 1898, he was requested to deliver to Washington, D.C. the report of the Spanish Naval Commission that investigated the loss of the battleship USS Maine in Havana Harbor. The commission's official report found that the cause of the explosion was most likely an "interior cause." Expecting to be returned to service at sea, he was immediately seconded to the Spanish Embassy at Washington, and assigned to the Spanish Empire office of Naval Intelligence.
Officially, Carranza was assigned the position of Naval Attaché, a positing traditionally used by many nations as a diplomatic cover for intelligence coordination since the late nineteenth century. He did not enjoy the assignment, believing himself better suited as a sailor. He maintained strong ties within the Spanish Admiralty and requested to participate directly in naval combat. He grew frustrated at being confined to intelligence duties, believing that Spain's chances of success depended on active engagement at sea rather than covert operations. Nevertheless, he performed his duties despite the hindrances of what he would later call the ineptitude of his superiors.
As the unofficial director of Spanish naval intelligence in Washington, Carranza relied heavily on Spanish immigrant networks in the United States. Communities in Tampa, Key West, New Orleans, and Mobile provided potential recruits and logistical support for intelligence and propaganda operations. Pro-Spanish sympathizers in those cities had allegedly raised funds to purchase a small warship for Spain and to conduct reconnaissance of American naval installations along the Atlantic coast. US field operatives also reported sightings of suspected Spanish agents as far west as San Francisco, allegedly engaged in surveillance of military facilities in the Bay Area. American intelligence later reported that Segismundo Bermejo, Spain's Minister of the Navy, had authorized plans to sabotage U.S. naval bases on both coasts. There were also fears that Spanish agents had infiltrated the U.S. Army and might reveal troop movements.
Challenge to a duel
As diplomatic conditions between the United States and Spain worsened, and the phenomenon of yellow journalism was stoking the fury of the American public toward war, General Fitzhugh Lee, the former U.S. Consul-General in Havana, and Captain Charles D. Sigsbee, the former commander of the USS Maine, provided testimony before congressional committees in which they expressed the view that Spanish naval officers might have been responsible for the destruction of the Maine.
Believing this to be a direct insult to the honor of Spain's naval service, Carranza sought permission from the Spanish Minister, Luis Polo de Bernabé – successor to Enrique Dupuy de Lôme – to issue formal dueling challenges to both Lee and Sigsbee. Bernabé forbade the act while Carranza remained an accredited diplomat, trying to maintain the reputation of the Spanish legation.
However, only shortly afterward, in April, conditions had worsened so much that the Spanish Embassy began preparing to evacuate its staffs to Canada, which was a neutral country. Bernabé agreed that that the challenges could proceed once relations between the two nations were severed. With the assistance of Captain de la Casa, the Spanish military attaché, Carranza prepared two letters of challenge, written in the formal language of dueling. A similar letter was sent to Captain Sigsbee, differing only in minor details. Both challenges were dispatched on April 20, 1898, when diplomatic relations between the United States and Canada were officially severed and the State Department granted the Spanish legation official passports. Carranza told members of the press that if Lee and Sigsbee wanted to take him up on the offer, they could find him in Canada.
History
Initial set-up in Toronto On April 21, 1898, the United States officially declared war on Spain, officially beginning the Spanish–American War. Spain strengthened its diplomatic presence in Canada by upgrading its consular posts in key Atlantic ports. New appointments included Joaquín Torroja in Halifax and Pedro Arias y Solís in Quebec City, both experienced diplomats who had previously served as Spanish consuls in Philadelphia and Tampa. On the Pacific coast, Spain also dispatched a young operative, Ángel Cabrejo, to Victoria, British Columbia. Cabrejo posed as a guardian to his sister, who claimed to be a student, but his true purpose was to observe maritime movements through the Strait of Juan de Fuca, the main approach to Puget Sound Naval Shipyard and the Esquimalt Royal Navy Dockyard.
Many members of the Spanish legation returned to Spain. However, Bernabé, Carranza, and their staffs in Washington boarded trains bound for Canada. Canada offered a number of advantages that made it an appealing base of operations for Spanish diplomats and intelligence officers. One key factor was the country's direct telegraphic and undersea cable connections to Europe, which provided a secure alternative to the U.S.-controlled communication lines that Spanish officials distrusted.
After leaving Washington, Bernabé and his staff traveled by express train to Buffalo and crossed into Canada at Niagara Falls. According to The Mail and Empire of Toronto, Bernabé immediately began sending and receiving a large volume of telegraphic messages upon his arrival on Canadian soil. Among his principal concerns was the safety of Spanish nationals employed in the cigar industry in Tampa, Florida, who were vulnerable to anti-Spanish sentiment following the destruction of the Maine.
As a result of Carranza's recent publicity, the Secret Service offered its "protection services" to the Spanish legation so that they would not be accosted on their journey. Secretly, they had been tasked by John Wilkie to observe their movements and collect intelligence. Four detectives were assigned to observe their movements, two openly and two covertly.
From Toronto, Bernabé informed Spain's Minister of State, Pío Gullón, that contact with Spanish authorities in Cuba could still be maintained through the Spanish consulate in Kingston, Jamaica. Small schooners were reportedly operating between Jamaica's northern coast and Santiago de Cuba to facilitate communications and transport under wartime conditions.
Setting up at the Windsor
Although Spain received polite denials of intelligence support from other European powers, its leaders continued to hope for sympathy from Catholic and monarchist circles abroad. The city of Montreal was the cultural epicenter of predominately Catholic French Canada. As the capital of Quebec, it was also the principal railway hub of Canada's railway system in 1898. Montreal offered convenient connections to New York, Halifax, and the Pacific coast. Its location also allowed for observation of shipping traffic moving between the Great Lakes and the Atlantic Ocean. In addition, the city's concentration of corporate headquarters and government offices enabled discreet contact with influential figures. For these reasons, Montreal emerged as the natural center of Spanish diplomatic and intelligence activity in Canada during the conflict.
Montreal already hosted a Spanish consulate general, headed by Eusebio Bonilla Martel, which provided a legitimate diplomatic base of activity. Toronto, by contrast, had only a vice-consulate staffed by an English-speaking Canadian, making it less suitable for accommodating personnel from the Spanish legation in Washington without attracting attention.
On 6 May 1898, members of the Spanish legation in Washington, including First Secretary Juan Dubosc and Ramón de Carranza, traveled by train to Montreal. Upon arrival, they took up residence in rooms 126 and 128 of the Windsor Hotel on Dominion Square and began coordinating their activities with Eusebio Bonilla Martel. Despite his objections, Carranza was ordered to establish his headquarters at the Windsor, where his superiors had already set up their offices. Carranza knew this was a bad idea; the hotel wasn't Spanish ground or even under the command and control of Spain, and was open to reservations by members of the public.
The Secret Service reserved the hotel room next door to Carranza, where they drilled holes in the walls and installed listening devices. Whether Carranza knew this is unknown, but in the lobby and the restaurant of the hotel, he was being monitored constantly by British, American, and Canadian intelligence officers. Not only that, the Spanish legation were being pursued by members of the Canadian press. There were also several Carlist agents staying here, monitoring the activities of the monarchist legation. There were so many intelligence officers in this hotel that they were literally "tripping over each other in the hallways."
George Downing, "the first Navy spy"
George A. Downing was a 33-year-old commissary yeoman who had recently been honorably discharged from the United States Navy. The position of commissary yeoman involved managing provisions and mess operations, roughly comparable to a modern logistics specialist. Downing was a naturalized former British subject who had reportedly served as a merchant sailor with P&O and as a crewman aboard a private yacht owned by a wealthy New Yorker.