One of the more flamboyant entries into the New York City scene was the Carolinian, Jonny Di Castillo. His involvement in bootlegging was comparatively shortlived, but the mystery and intrigue surrounding him is unmatched.
While he affected an Italian name and went to great pains to imply that he was a Made Man, the truth was revealed to all and sundry in the dawn of 1925 when his young cousin, Freddie McIntyre, came to town. Rather than being embarrassed by the Irish reveal, however, Di Castillo took it in his stride. None dated challenge him on it, though he never again alluded to the Mob.
From the outset, his motivations in bootlegging were clear - while he had access to some of the finest product available (and on that basis, was highly sought after as a supplier) he never pursued the career fulltime. He spent at least as much time carousing in the finest establishments and socializing with the City's elite as he did providing hooch. For the most part, these connections served him well: he spent several months cavorting with the daughter of a newspaper magnate; twice he was busted by the Police (on both occasions, his connections saw to it that the charges disappeared); he was invited to all the best parties, as a guest; and so on.
However, it was the same social aspect that led to his troubles and his eventual disappearance. Early on in his time in the City, he befriended an investigative journalist, Alice Spriggs. Indeed, rumor held that he was her lead for her expose of Mayor John Hylan While none of the allegations ever reached the stage of prosecution, none doubted that it contributed to his failure to obtain renomination in 1925.
In this same period, his connections with the party crowd tied him to the silent movie actress Lily L'Amour, who subsequently achieved significant notoriety in what became known as the L'Amour Affair. While Di Castillo was indisputably involved, his disappearance predates that venture's demise in Nairobi, Kenya.
It is unclear whether it was L'Amour or Spriggs who embroiled Di Castillo in the L'Amour Affair. As with so many other details of that escapade, the specifics are lost to history.
In piecing together what is known about the L'Amour Affair, from the collated court documents presented in Nairobi, from the medical transcripts of Freddy McIntyre, and from the personal papers of Jonah Kensington, the editor of Prospero Books and apparent backer of the L'Amour Affair's expedition, we can draw some conclusions about Di Castillo's movements in 1925.
Of the three sources available, the Kensington Papers are the most revealing, though they are also the most incriminating. They are relied on most heavily of the three, as they do include telegrams from Spriggs documenting the group's travels, and also the results of Kensington's own much later investigations.
On the formation of the core members of the Affair, a crime spree was embarked upon across New York City. This included the bloody and brutal murders of several African Americans in a Brooklyn hotel, burglary from a Harlem curios shop, the interrogation of a Professor of the Antiquities, and significant periods of public drunkenness.
Thereafter, the story becomes more grandiose. The expedition relocated to London, and under the pretext of investigating the Carlysle Expedition of 1920, or an Egyptological cult (the records show the group's motives vacillating between these two causes), the group is, at least, connected to: the Savoy fire, a major train derailment, two arsons in a country town, a car crash in Lesser Edale, a break-and-enter at the Penhew Foundation, and what appears to be a racially motivated incursion into an Egyptian Gentlemens Club of good standing.
These deeds behind them, the group moved on to Cairo. Their time in Egypt does not seem to be quite so criminal, though this may simply be a failure of adequate record keeping. Nonetheless, there were two significant events documented:
Firstly, the party visited the Bent Pyramid. The Kensington Papers make reference to an entirely undiscovered antechamber in the pyramid, housing some sort of Pharaonic automaton. By the time the group left the pyramid, some traumatic experience broke Freddy McIntyre's young mind and led to Di Castillo organizing the transit of his newly-catatonic cousin back to New York, to be admitted to the city's psychiatric institution.
The second event is more relevant for this narrative. It is only documented in the Kensington Papers, however, so it is not considered verified by any means.
According to those documents, the group found a network of secret tunnels under the Great Sphinx. In these tunnels, the group allegedly thwarted some dark cult ritual (by means of the cold blooded murder of an elderly woman). In so doing, they needed to cross a chasm, and having assured the safe passage of his colleagues, Di Castillo apparently fell to his death.
All we can ever know for sure is that Di Castillo disappeared in Egypt. Given the quality of the company he kept, the capacity for foul play by his associates can never really be ruled out.
Suffice to say, few others involved in bootlegging have a tale that can even hold a candle to that of Jonny Di Castillo.
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