Our Man in Moscow
An American Spy in Revolutionary Russia
In 1994, the security analyst Richard S. Friedman asked 61 intelligence veterans whether they were familiar with the World War One American spy, Xenophon Dmitrivich de Blumenthal Kalamatiano.
Despite his having something of a distinctive name, only two dimly recollected it. That was more than thirty years ago, when the War was just within living memory, so I think it’s safe to say that by now Kalamatiano has descended deeper still into the murky Hades of old spooks.
Which means it’s high time to rescue him from being a footnote to a footnote in the annals of intelligence history.
Annoying Plug: Exciting news for Spionage fans! I’ve selected numerous posts from this Substack, categorized them, edited them, deleted some stylistic infelicities, and made a few corrections, and have collected them into several, EZ-to-read “volumes” available for Kindle at $2.99 each. (Come on, don’t cavil at the price: This Substack is free.)
The series is called Tales From The Secret World. Titles include: Codes and Ciphers; Russians!; The Renaissance; and The World Wars.
Kalamatiano was an important figure in the history of American espionage. In the early years of the twentieth century, spying was in a transitory period between the gentleman-amateurs of the Victorian age and the professionals of the World War Two and post-War eras.
What what we would call “military intelligence” was carried out by officers seconded as attachés or observers to the various Great Powers, who would report home on troop strength, topography, armaments, expertise, and so forth that they saw during field exercises or gleaned from conversations with their well-heeled friends in the host army.
The future inventor of the modern airship (see my book, Empires of the Sky), Ferdinand von Zeppelin embarked on one such mission in 1863, when he spent several months touring the Union army during the Civil War. He duly submitted a report to his superiors in Württemberg concluding that there was nothing the Yankees could teach Germans about fighting. (And with that, Zeppelin missed the Battle of Gettysburg because he decided instead to travel to Minnesota, where he took his first flight in a balloon and the rest, to coin a phrase, was history.)
Another form of intelligence work was commercial in nature. This was generally coordinated through local consulates, with the consul or his deputy collecting information derived from traveling salesmen and friendly businessmen. Prices of goods, descriptions of new factories, supply shortages, Stock Exchange listings, trade scuttlebutt, and the like were of prime concern. Consuls were also expected to clip Press articles noting the departure and arrival of ships, rumored deals, and other newsy stuff and to send the package to the State Department every few weeks.
The U.S. consul in Liverpool, Thomas Dudley, about whom I wrote in The Lion & The Fox, thus sent home thousands of such pages during the Civil War. It was only because James Bulloch, a Confederate operative, showed up and commissioned a secret Southern navy that Dudley had to transform into the de facto head of Union Intelligence in Britain.
Getting back to Kalamatiano, he began his life in the secret world as a commercial informant, became a consular official in Russia, and ended it as a case officer running a network of agents for a nascent American intelligence service then beginning to grope its way towards institutional professionalism.
It’s that bridging of the old and new worlds that makes Kalamatiano interesting and important.
Kalamatiano himself could have stepped out from the pages of one of those Alan Furst or Eric Ambler spy novels featuring exotic émigrés of shadowy origins. He was born in Austria in 1882, the son of a Greek merchant (one presumably fond of the classics, judging by his choice of name) and a Russian noblewoman whose father was an admiral of the Black Sea fleet.
Xenophon’s father died in an accident when the lad was twelve, and in 1894 his mother married a young Russian-Jewish lawyer named Constantine Paul de Blumenthal.
Her new husband soon emigrated to America to take a job teaching languages at the Culver Military Academy in Indiana, founded that same year. Xenophon and his mother, then living in Russia, joined him a couple of years later, Indiana perhaps coming as a bit of a culture shock.
The marriage may accordingly have come under strain and there was a divorce in 1909.1 Anyway, that all lay in the future and in the meantime Xenophon took to America. He graduated with honors from Culver in 1899 and attended the University of Chicago on a scholarship. He majored in German and was awarded his B.A. in 1902. During his time in Chicago, he was a fraternity brother of Sigma Alpha Epsilon. (Such is Xenophon’s obscurity, he’s not mentioned among either Culver’s or Sigma’s eminent members on Wikipedia.)
In 1904, he joined the J.I. Case Threshing Machine Company of Racine, Wisconsin, and there his tale really begins. With his excellent German and almost-native Russian Kalamatiano was an ideal candidate to represent the firm in Europe, but most especially in Russia, where American companies were eager to expand their exports.
So off he went for several years, making valuable contacts and doing his best to sell threshing and other farm equipment to Russian businesses.
He was obviously good at his job, so good that his talents were in high demand by American companies. He soon switched from being a Case employee to a sales manager working on commission and so able to represent other firms, such as the John Deere Tractor Company.
By 1915, Kalamatiano was doing very well for himself and was appointed the American representative of the Russian Association of Commerce and Industry. As such, he had come to the attention of the the U.S. Consulate in Moscow as a helpful conduit of commercial information.
In the spring of that year, Kalamatiano moved to New York and become a vice president of the Nankivel Company, a business based at 120 Broadway specializing in exporting cars and trucks to Russia.
It was there that a former professor of his from Chicago, Samuel Harper, made contact and initiated Kalamatiano into the secret world—or at least its suburban outskirts.
Harper had friends in the State Department, who had no doubt verified Kalamatiano’s credentials with the Moscow consulate. It wasn’t top-secret material they sought; quite the opposite, in fact. They just wanted Kalamatiano to assist them to compile a list of American businessmen who, as he put it, “have shown a decided interest in Russian affairs.” Indeed, they were grateful when in 1916 Kalamatiano proposed setting up a program to help “American young men” go to Russia for a few years to learn the commercial ropes and pick up the language with “a view of using this knowledge as an asset in later life.”
This was hardly the stuff of James Bond, as you may have gathered, but it helps explain why Kalamatiano volunteered to return to Russia later that year. America had not yet entered the European war, and while the Russian front was wavering and the Bolsheviks were causing trouble, there were nevertheless rich pickings to be had for American exporters.
Thereafter, he circulated within the business elites in Petrograd and Moscow, gently steering contracts in favor of the Americans and passing on tips to his friends at the consulate, Maddin Summers (the consul) and DeWitt Poole (his deputy).
Precisely when Kalamatiano began spying in earnest is a little unclear. It was certainly after the overthrow of the Tsar in March 1917 and picked up steam following the American declaration of war on Germany in April. Kalamatiano himself recalled that it was in the autumn of 1917 that he mentioned to Summers that he intended to go home and enlist in the army, but Summers suggested instead that he stay “in Moscow and undertook certain work for the Consulate.” On November 5, accordingly, the State Department issued a passport for Kalamatiano to lend him diplomatic protection.
For the moment, Kalamatiano occupied a gray area between being a spy spy and a sorta-kinda agent. His recruitment happened to coincide with both Summers’ push to expand the consular system nationally to “render positive assistance” to interested American companies and the installation of the Bolshevik regime and the rise of the Whites against that government. By the spring of 1918, there was talk of an Allied military intervention and the Americans were keen to gauge, and encourage, anti-Bolshevik sentiment.
So it was about then that Kalamatiano’s role began to shift towards his becoming an active spymaster.
Kalamatiano was appointed to head the new “Information Service,” reporting directly to Poole, who had replaced Summers as consul after the latter’s death.
The Information Service was a hybrid beast. The Soviets were aware of its existence, but did nothing to hinder its activities. At the time, they were hoping to avoid antagonizing the Americans and, as Poole assured Foreign Commissar Georgy Chicherin, the IS’s business was simply to gather news on the political situation and economic conditions for the benefit of companies considering investing in Russia.
The part the Soviets were unaware of, though no doubt they had their suspicions, was that the Information Service had a clandestine side, one dedicated to penetrating the Bolshevik government and the Red Army. As Poole put it later, “in view of the Bolshevik totalitarian methods of government and their strict control of information, it was necessary to organize this on the well-known secret service system of cut-outs—that is, only two or three men were to know and have any contact with Kalamatiano. Then each of these men had two or three men in contact with him, and so on down, with the least possible cross-contacting.”
Well, that was the plan, anyway. The reality was that Kalamatiano would come to rely too heavily on a single agent to forward intelligence from the rest of the network. Dangerously, that agent, in other words, knew not just “two or three men” but everybody else, so if he was blown so too would be the entire network once the Cheka began its work.
It started well, though. By June of 1918, Kalamatiano had recruited “Agent No. 12,” Lieutenant Colonel E.M. Golitsin, formerly of the General Staff but now a chief of military mobilization and a senior figure in the censorship bureau. Through him, who was apparently a “right-wing” Socialist Revolutionary (SR) rather than a left-wing Bolshevik, Kalamatiano was put in contact with at least two more well-placed SR colleagues, such as a “Colonel S.,” a Hussars officer. Together they supplied maps of the various Red forces in Russia, news of White-aligned groups like the Czech Legion, and intel that SR sympathisers were planning “to lead things to a head in Moscow; i.e., turn out the bolshevicks [sic].”
Within a matter of months, quite incredibly, Kalamatiano succeeded in creating a network of some thirty agents, including a history professor at Moscow State University and a major-general in the Red Army named Zagryazhsky. Some of these were more productive than others; some presumably served only occasionally while others travelled around the country and sent in numerous reports.
His key man was the Latvian colonel Aleksandr Vladimirovich Friede of the Red Army’s Main Administration of Military Communications. How Kalamatiano managed to recruit someone so senior is a mystery, but a clue might be that one of the Russian auto brokers who’d worked at 120 Broadway during Kalamatiano’s Nankivel Company days was a certain Marcus S. Friede. Now, that could just be a coincidence, but it’s also entirely possible that Marcus was related to Aleksandr and so vouched for Kalamatiano with the colonel.
Whatever the case, Colonel Friede soon assumed the role of interlocutor between Kalamatiano and the rest of the network, abetted by his sister Mariya as courier. All messages from the various agents were collected and edited by Friede, who passed them to Mariya and thence they made their way to Kalamatiano.
It wasn’t until after American and Allied forces landed at Archangel and Vladivostock in the summer to help the anti-Red Whites that the Cheka turned its attention to cracking down on Kalamatiano’s operation. Diplomatic relations between the USSR and the West had reached near-breaking point and the vast majority of American officials departed the country. Kalamatiano, however, volunteered to stay, gambling that his Consulate cover would give him immunity.
He lost that bet. His network had already been penetrated. One Dmitri Ishevski, whom Kalamatiano had inherited as an agent from a Czech-run group, performed poorly and was fired by him, only to turn blackmailer, and, when that failed, offered his services to the Cheka. There were also, it seems, a number of other double agents and informers, including Mrs. Kalamatiano’s best friend.
The catalyst for Kalamatiano’s fall was the shooting of Lenin on August 30—which had nothing to do with the Americans, but led to fears of an Allied imperialist conspiracy against the government. In mid-September the Cheka swooped. They raided numerous apartments belonging to Kalamatiano’s agents, but the American miraculously evaded arrest.
Not for long, though. The Norwegians had taken over the Consulate as caretakers and Kalamatiano, using a Russian passport identifying him as Sergey Nikolayevich Serpovsky, a student, succeeded in sneaking close to it, so close that all he needed to do was sprint across the street, approach the gate, and seek diplomatic refuge. Alas, “there was however an armed guard, concealed in the janitor’s small house and I was surrounded and covered before I could get to the main entrance.”
Kalamatiano was taken to Cheka headquarters and kept in isolation for twelve days. For ten of those days, two to three times a day, he was interrogated by a trio of heavies: Jēkabs Peterss, the Latvian deputy chief of the Cheka regarded—and this is really saying something—as “the most bloodthirsty monster in Russia”; an Estonian Communist and Nosferatu-lookalike named Viktor Kingissepp; and the dandyish Armenian Lev Karakhan, Deputy Commissar for Foreign Affairs.
Befitting their admirably diverse backgrounds, they played different roles: Peterss, a former informant for the Tsarist secret police, was Bad Bully Cop, Kingissepp Ostensibly Reasonable Cop, and Karakhan Good Helpful Cop (offering “promises or rather suggestions of immunity”). Kalamatiano was repeatedly dragged out of his cell to face mock-execution and he never knew when the gun pressed to the back of his neck would contain a live round.
Kalamatiano, greatly to his credit, did not break but stuck to his story that he was an innocent assistant to the U.S. commercial attaché who happened to have a few chatty friends in high places. The Cheka did not, it’s safe to say, believe this, especially after they took apart a heavy cane he carried that contained a cipher code, cash receipts for payments, and a list of the thirty spies he’d recruited. This was somewhat incriminating evidence that Kalamatiano was not quite what he was claiming to be, and his carelessness in keeping it on his person is inexplicable.
Even if he’d destroyed it all, though, it wouldn’t have mattered. Virtually everyone else in his network, including his confidante Colonel Friede, had been rounded up and they proved willing to talk once the thumbscrews were tightened.
As sticklers for the legal process, the Cheka put Kalamatiano on trial on November 28, 1918. After five days of hearings, he was, inevitably, sentenced to death by firing squad—as was Friede—but on the very same evening Kalamatiano heard the verdict the Soviets temporarily commuted execution and he was held incommunicado “under particularly rigorous conditions” in a variety of prisons and camps for nearly three years.
Explaining the delay was that the Central Committee was divided on the question. The extremists, like Deputy Commissar Litvinov, were shrieking for the death penalty as soon as possible but the “moderates,” such as Chicherin, understood that Kalamatiano alive was more useful than dead. The Americans, they thought, would pay a high price to ransom him back.
The arguments went back and forth, but eventually, with Lenin backing the “hostage plan,” the moderate wing won out as the USSR descended into drought and famine. A secret deal with Washington was belatedly hammered out: In exchange for food aid from the American Relief Administration the Bolsheviks released Kalamatiano (and five other American prisoners) in August 1921.
A major stumbling block during the negotiations had been that the State Department refused to acknowledge, even when Kalamatiano’s old boss Poole was examined in a Senate hearing, that Kalamatiano had been a spy in the first place. The official story was that he was a volunteer enthusiast who had acted autonomously and without oversight, which made him come across as a rogue operator rather than as Washington’s man in Moscow. There was a nugget of truth to this in the sense that Kalamatiano had certainly exceeded his authority, especially after the departure of the Consulate staff, but the assertion that Poole and the State Department had absolutely no idea what he was up to is absurd.
Despite his three-year ordeal, Kalamatiano remained defiant and accepted full responsibility for being caught. Upon release, he requested several times to be sent either to Russia or to eastern Europe to continue his secret-service work but the State Department turned him down. Probably a wise idea. He might not be so lucky the next time he got caught.
Kalamatiano returned to the Culver Military Academy to teach but he had not long to live. During a hunting trip in January 1923 he suffered frostbite in his toes and developed gangrene. After several amputations, he seemed to make a complete recovery but in early November he relapsed—the cause was inflammation of the heart and anemia—and on November 9, he died, aged just 41 and soon forgotten after he was cremated in Chicago.
Note on the Three Interrogators: Swept up in Stalin’s Great Purge, Peterss would be arrested by the NKVD in 1937 and shot the following year. Lev Karakhan, too, came to a sticky end during the Purge and was tortured into confessing that he was a Nazi spy before being shot. Kingissepp predeceased Kalamatiano after being arrested by the Estonian Political Police in May 1922 and shot.
Further Reading: D.S. Fogelsong, “Xenophon Kalamatiano: An American Spy in Revolutionary Russia,” Intelligence and National Security, 6 (1991), 1, pp. 154-95; D.A. Langbart, “‘Spare No Expense’: The Department of State and the Search for Information about Bolshevik Russia, November 1917-September 1918,” Intelligence and National Security, 4 (1989), 2, pp. 316-334; H.T. Mahoney, “The Saga of Xenophon Dmitrivich Kalamatiano,” International Journal of Intelligence and CounterIntelligence, 8 (1995), 2, pp. 179-201; R.B. Spence, “The Tragic Fate of Kalamatiano: America’s Man in Moscow,” International Journal of Intelligence and CounterIntelligence, 12 (1999), 3, pp. 346-74.
Blumenthal would die in 1939 in Maryland, leaving behind a second Russian wife, a son, and a daughter (with another predeceasing him), the children being Russian-born circa 1911-13. I haven’t done a deep ancestral investigation, but this is what I’ve gleaned from his death notice.