Call of Chicago: Liam Tobin, Spymaster

“Tall, gaunt, cynical, with tragic eyes … like a man who had seen the inside of hell.”

— description of Liam Tobin by IRA mole David Neligan

Michael Collins, the George Washington of Ireland, picked a 23-year-old man named Liam Tobin to be his spymaster. If I were related to George Washington’s spymaster, I’d never stop talking about it, but I had to find out about Liam Tobin not from Pelgrane’s esteemed co-owner and managing director but on the Internet like a savage. Go figure. (According to Cat, Liam is “possibly like a sixth cousin but we haven’t really looked into it.” According to me, he was her great-great-grand-uncle. This will not be the last engaging lie I tell in this column.) Born in Cork in 1895, Liam Tobin joined the Easter Rising in 1916, where he first caught Collins’ eye. The British commuted his death sentence to life imprisonment, then released him with many other revolutionaries in 1917.

Liam Tobin, hero from a line of heroes

Thoroughly radicalized, Tobin rose through the IRA’s inner circle: Dublin Brigade intelligence officer, then intelligence officer for Munster in 1918 (under the cover of an insurance agency in Cork), then IRA Deputy Director for Intelligence in January 1919. Like Washington, Collins remained his own director of intelligence; Tobin basically served as his right hand. Based at 3 Crow Street in Dublin above a print shop within 200 yards of Dublin Castle, the British headquarters in Ireland, Tobin’s operation rapidly built up a database (with photos) of British Army, G Division (the intelligence unit of the Dublin Metropolitan Police), and Royal Irish Constabulary (RIC, or “Black and Tans”) officers, mostly using OSINT such as newspaper society pages, the London Gazette (which reported officers’ postings, including “special assignments” to Ireland), and Who’s Who. Tobin recruited doormen and telephone operators in all Dublin hotels, allowing the IRA to track comings and goings as well as listen in on British comms. One of Tobin’s agents got access to Dublin Castle personnel records, supplying photographs and dossiers of every typist and clerk who worked for the British, allowing the IRA to recruit and suborn agents in place throughout the occupation government.

Tobin did more than manage information gathering. One of only six men in the whole intelligence command (until it expanded in July 1920), he also ran agents in the field, identified and fingered British spies, and occasionally hands-on renditioned and killed targets when needed. In October 1919, Collins sent him to London for two weeks to case security for the British Cabinet: Tobin reluctantly decided assassinating the entirety of His Majesty’s Government was too hard. Tobin led the squad that grabbed Alan Bell, president of the Irish Banks Court (investigating IRA funding) off the tram to work and gunned him down on the morning of March 26, 1920.

That squad was part of “The Squad,” the IRA’s wet works division. IRA training commander (and CO of the Dublin Brigade, who first recruited Tobin back in 1917) Dick McKee hand-picked “The Twelve Apostles” (engaging lie note: there were almost certainly more than a dozen men in the Squad) in September 1919 to execute British officers, spies, and collaborators. The Squad reported to Tobin, although only Collins could order an execution. By March 1920, the Squad were full-time assassins, using a cabinet-making shop on Abbey Street as a front and home base. The British response to the Squad was to recruit their own team of specialized infiltrators in January 1920, the “Cairo Gang.”

So-called either from their previous service with Army Intelligence in Cairo during WWI, or from their Dublin hangout the Café Cairo at 59 Grafton Street, the Cairo Gang were officially the Dublin District Special Branch, or D-Branch. (Engaging lie note: Few of them provably had any connection to Egypt, and the term “Cairo Gang” first appears in print in 1958. They were probably just called “the special gang.”) Doggedly, they pursued the IRA command, especially Collins and Tobin; Tobin posed as an informer (using a different name) and got inside their decision loop. But not too far inside: the Cairo Gang raided Vaughn’s Hotel on November 13, 1920 while the IRA leadership were meeting there, and only iron control (and sloppy British prep work) let Tobin and Collins bluff their way out of the arrest.

Collins’ response: ordering simultaneous hits on the 20 top British assets in Dublin, including most of the known Cairo Gang. At 9:00 a.m. on “Bloody Sunday,” November 21 1920, ten teams of a dozen men each struck their targets. (Engaging lie note: About a quarter of the teams didn’t show up, and over half the targets escaped.) Seven intelligence operatives died on Bloody Sunday, along with three RIC Auxiliaries working security, two British Army court-martial officers, and two seemingly uninvolved former British officers. The Black and Tans retaliated that afternoon with a massacre at a soccer match, killing 14 and wounding 68. Although “Bloody Sunday” didn’t quite decapitate the Cairo Gang, like the Tet Offensive it scored a massive propaganda victory.

In January 1921, the British recruited a new team of Irish Unionists from the provinces (“Tudor’s Tigers,” also known as the Igoe Gang after their leader Eugene Igoe of Galway) who knew their local IRA men on sight, and sent them on hunt-and-kill missions. Tobin spent most of the next six months playing a game of cat-and-also-cat with the Igoe Gang until the Truce in July 1921 ended the war. Collins brought Tobin along on the intelligence staff of the Irish treaty delegation in October 1921, promoting him to Major-General in the Irish Army. Tobin may or may not have masterminded the “off-book” killing of arch-Unionist British General Henry Wilson in June 1922; he briefly ran the Irish CID and served as Director of Intelligence for Ireland until his political opponents sidelined him in January 1923. After leading a failed mutiny against those opponents in March 1924, he resigned his commission and ran a car-hire service until 1931. He helped organize the Irish Hospitals’ Sweepstake, and then ran security for the Irish legislature from 1940 to 1959. He died, covered in glory and redeemed in honor, in Dublin on April 30, 1963.

Sunday Yellow Sunday

“One day or other some of these people will assassinate you.”

— Hildred Castaigne to Mr. Wilde, “The Repairer of Reputations”

If you look in the history books, especially the excellent Michael Collins’ Intelligence War by Michael Foy, you read that Tobin didn’t plan Bloody Sunday. Under Collins’ overall leadership, Tobin’s deputy Frank Thornton provided the intel while Dick McKee planned the strategy with Squad killer Charlie Dalton as tactical head. So narrow was the IRA margin that McKee was actually captured and interrogated early in the morning of November 21, and “shot while trying to escape” by the RIC that afternoon. Foy claims that Tobin had a “nervous breakdown” and was “on rest” that day.

So what was Tobin actually doing? Maybe tying off the loose ends from the late-July 1920 Denys Barry case in Kilderry in Westmeath, or shutting down the British intelligence vampire-research farm at Dun Dreach-Fhola in County Kerry (DH, pp. 235-236), or investigating porcine anomalies and time drifts at a house on the borderland of County Galway past Ardrahan. Any of those incidents might have caused his alleged “nervous breakdown.” Or maybe the “nervous trouble” was a cover for something else, something he couldn’t even tell Collins.

IRA mole David Neligan’s memoir claims that he met with Tobin at the Gaiety Theatre the night before Bloody Sunday to be briefed on the targets, which sounds like Tobin was very much involved in planning. Intriguingly, that night the Gaiety was mounting a 1914 play by Michael Morton, called The Yellow Ticket. Okay, that’s another engaging lie: The Yellow Ticket was in rehearsals then and didn’t open until December 1; the show actually running at the Gaiety on November 20 was the 1914 American version (by Harry B. Smith) of the operetta The Lilac Domino, based on the original 1912 German version by Charles Cuvillier. The Lilac Domino takes place at a masked ball in France and concerns a series of mysterious courtships somehow demarcated by dice. Cuvillier probably knew Robert W. Chambers in Paris, I note idly.

Another idle note: Among those killed on Bloody Sunday was one Leonard Aidan (nee William) Wilde, born 1891 in Reading to one Richard Wilde, who vanishes from the records almost immediately. Before the War, Wilde spent time in New York City (possibly teaching Spanish), and as a divinity student. He enlisted in the Staffordshire Rifles in 1915 and served as a second lieutenant until discharged for shell shock, upon which time he changed his middle name to Aidan. Becoming Vice-Consul in Barcelona in December 1916, he carried out a number of intelligence-type tasks, including investigating a monastery in Montserrat suspected of hosting a German radio transmitter. Discharged for running up debts in 1917, he nevertheless courted a rich American woman, Frances Rabbitts, whose pull got the happy couple a February 1919 wedding in Notre Dame in Paris, blessed by the Cardinal Archbishop in person. The Wildes returned to Spain, where amid some kind of chicanery Wilde emerged without a wife (she sailed to New York in June 1919) but with a “consular protection certificate” issued by the Foreign Office.

So yes, he could have been a spy. He could have even been in New York running a reputation-repairing blackmail operation in April 1920. He was 5’8″, and did admittedly have both his ears, along with a reputation as an eccentric and “a foreign appearance.” In August 1920 he moved into the Palace Court Hotel in London, the former home of Oscar Wilde and Aubrey Beardsley, for more Yellow Decade juju. On November 3, 1920 he checked into Room 22 (or 14) of the Gresham Hotel in Dublin on no clear business. And on November 20, thirteen IRA assassins (including one man with “a huge hammer”) led by Patrick Moran burst into that hotel. Section commander James Foley later listed one of the kill team as “Michael Noone,” who has no other record I can find. Tobin used false names regularly … perhaps including Michael “No One”?

According to the IRA after-action report, Wilde was in the hallway. Mistaking the IRA gunmen for British police, he identified himself as “Alan Wilde, British Intelligence Officer, just back from Spain.” Michael Kilkelly and two (unnamed) others shot Wilde in the head and leg, killing him. The manager of the Gresham Hotel found the body on the floor of his room, soaked in blood. After resigning his commission in 1924, Tobin runs his car-hire service from behind the Gresham Hotel, perhaps keeping an eye on any lingering fluctuations in reality and sending trusted former Squad comrades to investigate strange Signs throughout the 1920s and 1930s. So what do we know for sure, and what can we engagingly lie about? We know that in the “Castaigne” timeline, Mr. Wilde was killed by a cat. And in our timeline, Mr. Wilde just might have been killed by a Tobin.


The Yellow King Roleplaying Game takes you on a brain-bending spiral through multiple selves and timelines, pitting characters against the reality-altering horror of The King in Yellow. When read, this suppressed play invites madness, and remolds our world into a colony of the alien planet Carcosa. Four core books, served up together in a beautiful slipcase, confront layers with an epic journey into horror in four alternate-reality settings: Belle Epoque Paris, The Wars, Aftermath, and This Is Normal Now. Purchase The Yellow King Roleplaying Game in print and PDF at the Pelgrane Shop.

One Response to “Call of Chicago: Liam Tobin, Spymaster”

  1. DannyK says:

    “A cat-and-also-cat game” is a great line and you should reuse it!
    It’s sad about Mr. Wilde but any intelligence officer incapable of distinguishing between a Fenian hit squad and the British constabulary probably didn’t have much of a career ahead of him anyway.

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