In 1917, F. Scott Fitzgerald, author of The Great Gatsby, was nearly recruited for a covert mission to Russia, posing as a Red Cross secretary for Father Sigourney Fay. The mission, tied to US State Department interests during the Russian Revolution, aimed to gauge religious freedom and political shifts. Complicated by secret diplomacy and escalating unrest, the mission was likely aborted, leaving Fitzgerald with only the memory of how he almost became a spy!
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In August 1917, the 20 year old Scott Fitzgerald received a letter from his prep-school mentor, Father Fay. America had entered the war in the spring, a momentous event in itself, but an event that coincided with another momentous event when the people of Russia deposed Tsar Nicholas II in the February Revolution. Fay’s letter reached out to Scott whilst he was still at Princeton University, waiting to enlist. By this point in time, the former leader of the Socialist Revolutionary Party, Alexander Kerensky, had been elected as Prime Minister of Russia’s new Provisional Government under his breakaway party, The Trudoviks. As a key influencer in the US State Department’s bid to romance the Vatican and get their backing for their war with Germany, Fay had been selected for a three-month ‘secret mission’ in Moscow and Saint Petersburg. In the summer that year, Fay had written to Scott sounding him out about the mission and the possibility of him tagging along as his personal secretary. Scott had accepted the challenge and duly drummed up the $3600 required to cover the cost of travel and living expenses. In August 1917 Fay wrote back delighted with his decision and explaining the state of play:
“In the eyes of the world, we are a Red Cross Commission sent out to report on the work of the Red Cross… and that is all I can say. But I will tell you this, the State Department is writing to our ambassador in Russia and Japan, the British Foreign Office is writing to their ambassador in Japan and Russia, and I have other letters to our ambassador in Japan and Russia, and to everybody else in fact who can be of the slightest assistance to us … To my mind the most extraordinary thing about it is that we may play a part in the restoration of Russia to Catholic unity.” [1]
Details about the mission remain rather sketchy, but the most plausible explanation is that Fay would be there to observe the sincerity of Kerensky’s pledge to allow the floodgates of Catholic worship to open and spread among its Greek and Slavonic populations. The fall of the Tsar had meant an immense stumbling block to worship was being removed. A new era of religious tolerance was said to be emerging, but nobody knew for sure how quickly and how far any of it was likely to go. The battle for Catholic emancipation was just beginning and the US State Department, like their counterparts in London, were anxious to know who was winning and what kind of regime they were dealing with. Fay told Scott that officially they would be in Russia on behalf of the Red Cross, but he also intimated that there was a lot more to it than that. If anybody was to ask, he was to say he was a Red Cross officer and nothing more. As far as Russia was concerned the pair would be there to observe the progress of the relief effort under its chief, Raymond Robins.
The man who had conceived of the Commission, and who was paying for it all, was Wall Street banker, William Boyce Thompson. Boyce had his own reason for being in Russia. Under the cloak of a humanitarian mission, he was there to oversee the formation of a fully democratic government and explore new business opportunities for himself and his associates back in New York. George Kennan would later write that the Commission was neither needed nor particularly wanted by the Russian government, and that by September 1917, they were viewing it with enormous scepticism. Convinced that he and his team were being exploited, the head of the Commission, Frank Billing, returned to America in mid-September, “sick and disappointed.” Years later he would write that the Red Cross dimension of the mission had been nothing more than a mask.

Passport applications were made out by Fay and Scott in August to travel from Vancouver on September 27 on the Empress of Russia, but by mid-September things took a turn for the worse. Russia’s people were getting fractious. There was still no sign of peace and Prime Minister Kerensky’s already weak grip on power was declining daily. As a result, Fay’s plans were put on hold. To make matters worse, rumours were being heard that maximalist factions in Russia had been discussing peace deals with Germany. If true, the allies were finished. [2] The plan devised by the US State Department had been to take the route through Japan and the Pacific to avoid submarine warfare in the Atlantic. Having an experienced pair of eyes on the ground in Russia would have been vital in assessing the reality of the situation. In October, a brand new Russian Ambassador had been appointed to the Vatican and the allies were anxious to know if the promise of freedom of worship (and conscience) to Catholics in Russia held any water at all. With the arrival of Russia’s first Catholic Ambassador M. Lyssakowski at the Vatican in October things were beginning to look more positive, with the years of persecution suffered by Catholics under the Tsar looking increasingly likely to end. Fay’s friend and Scott’s literary mentor, Shane Leslie, had been earmarked to go too, but as he was not an American citizen he was excluded from representing the neutral interests of the Red Cross. [3]
Within weeks of Fay writing to Scott about the plans of the US State Department, the most unexpected thing happened. Refusing to accept the abdication of the Tsar and the relative absence of his Royalist supporters in government, the belligerent Tsarist General, Lavr Kornilov led a coup against Kerensky. As a result of the crisis and the risk of further escalations in violence, the whole mission was shelved indefinitely. [4] As neither Fay or Fitzgerald are mentioned in the official war council report in November 1917, it may be fair to surmise that Fay’s ‘burn after reading’ instructions to Scott had masked some genuine intrigue. [5]
After the Bolshevik revolution began to shape in October 1917, it is said that plans for the trip were aborted. However, there are a two items in the archives that challenge this notion. In a letter from their mutual friend, Father Hemmick to Shane Leslie in October 1917, Hemmick writes that he had heard that Fay had already set off for Russia “with Fitzi as secretary and an orderly.” [6] A review of Fay’s passport application for Italy a few months later in December 1917 provides another clue. In the section where Fay was asked to provide information about places outside the US in which he had resided, the priest writes that he had been “a member of the Red Cross Commission to Russia in 1917 and had a passport” at that time. [7] If Fay hadn’t made the trip to Russia, then it is a mystery as to why he would say he had. There are few clues in either Scott’s ledger or his letters that would confirm it either way.
In his ledger, entries for this period suggest that Scott meets with Fay twice: once at Deal Beach in New Jersey in October 1917 and again in November, just before leaving for Fort Leavenworth to complete his basic training. In a more ambiguous reference, Scott writes to his friend Edmund Wilson in the Fall of 1917 explaining that he had been intending to write to him sooner but that had “had a change of scene” and that the “necessary travail there” had “stolen time.” [8] Although we know that Scott was required to complete his passport application form for the trip on the Empress of Russia on September 27th that year, there’s no firm evidence that he ever went. A letter from Fay to Scott dated October 4 from New Jersey, suggests that if they did go, then it was sometime between the second week in October and mid-November, when Scott writes to his mother. [9] It may yet transpire that Father Fay did embark on his trip to Russia, just not with Scott. Perhaps anxious to spare Scott’s feelings or risk undermining his confidence, he had simply chosen to tell told him that the mission had been called off — we just don’t know.
Whatever did or did not happen in Russia, Scott had also been earmarked to accompany Fay to Rome, but for whatever reason, Fay ended up going alone. A letter from Fay to Scott just days before he embarked for Rome describes the excitement he was feeling about the mission:
“Have been made Major and Deputy Commissioner for Italy. I am going to Rome with a wonderful dossier, and there will be “no small stir’ when I get there. How I wish one of you were with me. This sounds like a rather cynical letter. Not at all the sort that a middle aged clergyman should write to a youth about to depart for the wars. The only excuse is that the middle aged clergyman is talking to himself. There are deep things in us and you know what they are as well as I do.”
In the same letter Fay reveals his interest in the young man’s literary ambitions. Although he still thought Scott should be working on a book of poetry, he said that if he was determined to complete his novel, he thought it should be called The Romance of an Egotist. He also admitted that he’d been contacted by Leslie and thought Scott would be delighted to learn that he now thought of him as “the Rupert Brook of America.” [10]
According to Shane Leslie it had been William Wiseman, chief of British Intelligence in New York and Washington in the early years of the war, who had first floated the idea of using a “confidential agent” in Rome. Although the idea had been put to President Wilson by the British Ambassador, Lord Reading, it was believed to have come from a series of private discussions between the President’s Catholic adviser Joseph P. Tumulty and Wiseman at his new HQ in Paris, with Shane Leslie, who was close to both, acting as intermediary. [11] It’s entirely likely that the scheme to plant Fay and Scott in Russia had been conceived by the same group — the Irish and Catholic questions both remaining critical to allied objectives. Wiseman had been unconvinced about the impact that Red Cross chief Raymond Robins was having in Russia and relayed his concerns back to Wilson’s most trusted adviser, Colonel House, one of the 2600 passengers who would accompany Scott and Zelda on the RMS Aquitania to London in May 1921. [12]
Leslie and Fay had both been in Russia in 1907 — Fay accompanying Bishop Charles Grafton of Ford Du Lac and Leslie on a year-long tour of the country arranged by Maurice Baring (and old acquaintance) and Alexander von Benckendorff, the Tsarist Ambassador in London — also a Roman Catholic — who had played a key part in organizing that year’s Anglo-Russian Agreement. [13] Travelling with Baring, Leslie had found Russia to be one of the most religious countries in the world. Whether it was the remote farmlands of Sosnóvka or the heavy, political centre of St Petersburg, trains were in no hurry, and in place of waiting rooms at the stations, they had chapels. [14] In a letter to his Princeton friend, Edmund Wilson, Scott had reminded him that 40% of the men in America’s army were Irish-Catholics. [15] The church’s role in managing opinion among Irish-Catholics was immense. As Washington’s wirepuller at the Vatican, Fay was making every attempt to grind down the Pope’s resolve on remaining neutral in the war with Germany.
In Leslie’s opinion, it was Father Fay’s own dogged determination to get things done and deals agreed that had led to his early death in January 1919. The British Foreign Office and US State Department were demanding solutions and reconciliations, and after months of constant, exhausting travel, Fay was providing them in abundance. The only thing he sought in return was a place at the table for the Church and the Irish at the upcoming peace conferences in Paris. He died suddenly in New York on the eve of his trip London to negotiate. In his memoirs, Shane Leslie would recall an incident in which Fay had literally thumped his fist on the table in an attempt to impress his message on the Pope. According to Leslie, Fay’s frankness had pleased Pope Benedict who was “able to judge the future better and to discount previous informants”. In another diary entry, Shane revealed that the British Foreign Office thought Fay a more effective source of information than the President’s own official adviser, Colonel House. Leslie revealed that after arriving in Rome as a courier of secret messages from the White House Fay had been followed to the Vatican “by the Secret Service of three nations.” Operating under the disguise of a Red Cross officer, and looking portly and faintly amusing, Fay was being regularly trailed by spies desperate to know what sanctions he was carrying. [17]
In 1918, Leslie would provide Fay with a series of ‘secret letters’ prepared by members of the American government for use during his talks with the Pope on matters in Europe and the Irish Question. [16] Born to a powerful American mother and an Anglo-Irish landowner, Leslie had been supporting British Ambassador Cecil Spring Rice in his bid to win the support of Irish-Americans in the pro-war effort in Washington D.C. The work he did would consist of promoting films, books or news items that furthered the aims of the war and kept the hearts and minds of the American public firmly on the side of the allies. Whilst there is much uncertainty about his exact role, a letter written by Leslie to his aunt, Jennie Churchill, offers some tantalising clues. Of his activities in the US he would say nothing more “except to say quite privately that I am not unemployed though you must not ask how”. In another letter he had warned his mother, Leonie Leslie, not to write to the Foreign Office or discuss his activities with others. [18]
One can only imagine the initial thrill Scott Fitzgerald would have felt when he received his letter from Fay. The adventure they had ahead of them would have seemed every bit as gripping as the stories told by his father about the spies of the Civil War. In June 1921 he would spend time in the company of staff from the British Embassy in Rome. Britain’s Ambassador in Rome at that time was George Buchanan, the man who just four years earlier was heading the British Embassy in Russia. In all liklihood, Scott would have sat in the bar with a gin in his hand, regaling the embassy staff with his tale of how he ‘nearly’ became a spy.
[1] ‘Dear Fitz, August 22, 1917’, Sigourney Fay, Correspondence of F. Scott Fitzgerald, Bruccoli, p.18-19
[2] Sigourney Webster Fay, August 17, 1917, Passport Applications, January 2, 1906 – March 31, 1925. The details suggest he was going to take the route to Russia via Japan on the Empress of Russia on September 27, 1917 (in the interest of the Red Cross)
[3] The Anglo-Irish baronet Shane Leslie was a friend of Fay and employed by the British Foreign Office to work in Washington during the War on Irish and Catholic propaganda. Leslie was the first cousin of Winston Churchill. Their mother were members of the American Jerome family.
[4] ‘Dear Fitz, Father Sigourney Fay’, August 22, 1917, Correspondence of F. Scott Fitzgerald, ed. Matthew J. Bruccoli, Random House, 1980, pp.19-21
[5] For the official Red Cross Commission led by Billings, Thompson had paid for everything, including uniforms. In his letters fay says that all costs of passage, including Red Cross Uniforms, would have to met by Scott and himself.
[6] Letter to Shane Leslie, William Hemmick, October 1917, Box 10, Folder 13, Sir Shane Leslie Papers
[7] Sigourney Fay, December 9, 1917, Passport Applications, January 2, 1906 – March 31, 1925
[8] ‘To Edmund Wilson, Fall 1917’, F. Scott Fitzgerald, A Life in Letters, p.11
[9] Ibid, p.13
[10] ‘Dear Fitz, December 10, 1917, Father Sigourney Fay’, Correspondence of F. Scott Fitzgerald, Random House, 1980, pp.23-24
[11] British-American Relations, 1917-1918; the role of Sir William Wiseman, Wilton B. Fowler, Princeton University Press, 1969, pp. 160-162
[12] Soviet-American Relations, 1917-1920, George F. Kennan, 1958, Princeton University Press, p.208
[13] Sublime Failure: Shane Leslie, Otto Rauchbauer, pp. 89-91; ‘Death of Monsignor Fay’, The Catholic Columbian, Volume 44, Number 3, 17 January 1919, p.7. ‘Religion in the Balkans’, Washington Post, February 14, 1913, p.5; ‘Many Catholics Hear Dr Fay’. The focus of both trips been related to matters of the Church (rapprochement between the High Anglican, Episcopalian and Orthodox Church of Russia — Fay and Leslie had yet to convert to Catholicism). Fay had also visited Russia in 1903-1904.
[14] Long Shadows, Shane Leslie, p.114
[15] ‘Dear Bunny, Fall 1917’, Letters of F. Scott Fitzgerald, p.325
[16] Shane Leslie: Sublime Failure, Otto Rauchbauer, p.49.
[17] ‘This Side of Paradise’, Shane Leslie, Dublin Review, October-December 1920: Vol 167 No.335, pp.288-289
[18] According to Professor Otto Rauchbauer, Leslie was staying at the home of Alice Lee Roosevelt Longworth, the eldest child of President Theodore Roosevelt (2127 Leroy Place). Cecil Spring Rice (also Anglo-Irish) had been a very close friend of Theodore Roosevelt. In January 1919 Leslie returned to New York where he stayed at 128 West 29th Street, a few yards down from The Plaza.