Missing Over Cuba, $25,000 Reward

lsc620417rorkeOn 24 September 1963 Alexander Irwin Rorke climbed into a twin-engine plane at Fort Lauderdale airport. He was never seen again.

The good-looking 37-year-old with black hair and blue eyes was a well known figure in the murky world of Florida anti-communism. He had been a free-lance photojournalist in Cuba covering Fidel Castro’s revolution until critical comments about the new regime’s leftward drift got him in trouble. Some jail time and a deportation order later, he was up to his neck in CIA agents, right-wing Cuban exiles, soldiers of fortune, and ultraconservative American patriotism.

In 1961 he scattered anti-Castro leaflets over Havana by plane. The next year was secret boat trips to Cuba for guerrilla warfare. Early in ’63 he was back in the air, bombing a Cuban oil refinery. FBI agents warned him off. Rorke ignored them.

Now he had another mission.

A Man of Means

When Rorke failed to return, his hysterical wife called her father. Sherman Billingsley was a 67-year-old nightclub owner who’d never really liked his son-in-law. He wouldn’t even allow him in the house. When Jacqueline brought little Alex III by for visits, Rorke had to wait outside the mansion in the car.

Billingsley had convinced himself that marriage to a slick charmer was just a bit of rebellion by his favourite daughter. Her sobbing voice on the telephone finally convinced him otherwise.

“Oh my God, you really loved him,” said Sherman Billingsley in surprise.

He reached out to his contacts. Billingsley was an influential man, owner of the Stork Club, exclusive night spot for the famous and rich. Ernest Hemingway, Orson Welles, and Ethel Merman had all been regulars. These days the club was on the slide but Billingsley still had important friends, most of them prepared to overlook stories of his youthful bootlegging adventures.

He asked the FBI for help.

The War Veteran

Billingsley knew Rorke as the well-off son of a Manhattan District Attorney and owner of a vending machine business. A no-good rich kid who hammered a wedge into the Billingsley family by eloping with Jackie. But the FBI file had some surprises.

Rorke had served as a young paratrooper during the war then moved into military intelligence in occupied Germany. His enthusiasm for anti-communism began when he helped round up Soviet agents in the American zone. A brief stint as a file clerk in the FBI followed his military service  but it didn’t work out and Rorke went off to St John’s University in New York and the Georgetown University School of Foreign Service.

He met Jackie Billingsley in New York back in the early 1950s. She was a wavy-haired blonde with painted eyebrows and a face just the right side of hard. It was love, even if Jackie’s father didn’t think so. They married without Sherman’s permission at the Roman Catholic Church of the Holy Trinity on West 82nd Street.

Rorke spiced up his life with some freelance journalism for the Hearst Organisation. Suspicious minds would later claim it was all perfect cover for a spy who never really left the spook world. The truth may have been simpler: Rorke was just a restless war veteran with too much money and a taste for adventure.

Either way, he was in Cuba during the revolution and did some prison time for being one of the first to spot the creeping communism in Castro’s rule. After being deported, Rorke began to spend time in Florida with Cubans who had washed up there to escape the new regime. It was a melting pot of right-wing resentment and paramilitary groups, funded by genuine patriots, casino owners who wanted their property back, and Mafia-types who had been bleeding the island dry for decades.

The CIA was there too.

Bay of Pigs

On 17 April 1961 the exile paramilitary unit Brigade 2506 tried to overthrow Castro. The resulting catastrophe became known as the Bay of Pigs Invasion.

The CIA had been training the Brigade since the previous year, using middlemen and sympathisers to claim the funding came from a Cuban millionaire. No-one was fooled. It was an open secret in Miami that the American government was helping the exiles get their country back.

jfkThere is no evidence Rorke had any contact with the Brigade but he was prominent enough in the anti-Castro movement that the CIA got in touch with him. He helped run a number of organisations, some Cuban, others formed by anti-communist Americans; he gave military training to paramilitary groups, spoke at conferences, wrote press releases. The CIA found him loudmouthed and fanatical but useful.

As a true believer, Rorke did not abandon the cause when the Bay of Pigs Invasion turned into a dramatic failure. Castro’s forces were waiting for the exiles and killed hundreds in three days of fighting. The survivors marched into prison camps. One of the dead was Alejandro del Valle, son of a mercenary who fought for Haile Selassie back in the 1930s. America denied any involvement in the invasion but couldn’t find anyone prepared to believe that.

In the aftermath the CIA quietened down its activities in Florida. Rorke carried on being as loud as ever, dropping leaflets over Havana in late ’61 from a twin-engine Beechcraft he co-owned with twentysomething pilot and Air Force veteran Geoffrey Francis Sullivan. In 1962 he was making secret boat trips into Cuban with fellow exiles for guerrilla raids and a reported assassination attempt on Castro.

When the boat was confiscated, first by the British and then American customs authorities, Rorke was unhappy the CIA refused to help him get it back. By the summer of 1962 the CIA, which had been “counselling” him and funding some of his activities, dropped him completely.

“A loose talker,” it said.

Rorke didn’t care. Not even the Cuban Missile Crisis of October 1962, when the world came to the brink of nuclear war, could deter him from his anti-communist crusade. He carried on the fight.

Burning The Midnight Oil

By 1963 Rorke was splitting his time between New York and Fort Lauderdale. Jackie and Alex III moved down to Florida to see more of him.

At the end of April 1963 he appeared in Washington DC at a meeting of the Anti-Communist Liaison Committee (he was one of the Committee’s leaders) and announced he had just returned from a night time bombing mission against an oil refinery in Cuba. Suddenly he was all over the news and a hero to American anti-communists.

It wasn’t all welcome publicity. The Treasury Department tried to seize the Beechcraft aircraft and fined Rorke and Sullivan $500 each. The FBI investigated. They found Rorke in New York’s Dover Hotel complaining that Sullivan and the Beechcraft had played no part in the raid: it had been carried out by Cuban exiles in a PBY flying boat that picked up Rorke and some companions after they sailed out of Miami.

He seemed upset that more than a few journalists refused to believe the raid had taken place. The FBI agents must have shared the scepticism because Rorke rang their offices a few days later to report a Havana radio broadcast describing the attack. The FBI later confirmed his story, along with the detail that the home-made napalm bombs Rorke helped tip out the airplane door had failed to explode.

The FBI suggested he might want to tone down his activities. Rorke told them the Department of Justice had a vendetta against him. The agents left not believing the all-American activist had any intention of abandoning the Cuban exile cause.

The Last Flight

In late September Rorke told his wife he was flying to Nicaragua. The Treasury Department had apparently released his plane and Rorke wanted to see Nicaraguan dictator Anastasio Somoza Debayle about founding an import-export business. It may have been true but Somoza’s country was anti-communist enough to be a useful base for more missions against Cuba. Many exiles outside Florida carried out their activities from locations in Central America and the Caribbean.

mugshots2Or the whole thing may just have been a cover story. When Rorke and Hamilton (somewhat jittery about this flight, the pilot’s wife noticed), and a Cuban exile called Enrique Molina Garcia boarded the plane at the Fort Lauderdale they filed a flight plan for Panama. The trio set off, refuelled on the Mexican island of Cozumel, then filed another flight plan for Honduras.

Then they took off and disappeared forever.

Sherman Billingsley was one of many who assumed they had headed for some covert mission over Cuba. He offered a $25,000 reward for their return during a press conference at the Stork Club.

The money was never claimed and Alexander Irwin Rorke was declared legally dead in 1968.

The Usual Conspiracies

No-one knows what happened to Rorke, Hamilton, and Molina Garcia but that hasn’t stopped the speculation. Some claim Molina Garcia was a former Castro loyalist prison guard who joined the opposition and was never trusted in the exile community. They dream up schemes where he delivered the two Americans into the hands of the communists. Others like to point out that Rorke had earlier been associated with the American Frank Sturgis (aka Frank Fiorini), a former military man and nightclub owner who fought alongside Castro during the revolution before defecting in 1959. Some suspect he had tangled loyalties. They point to Sturgis’ role as a CIA informer and future Watergate burglar.

Researchers into the November 1963 assassination of President John F Kennedy believe Rorke’s presence in the American anti-communist hard-right is evidence of some connection to a conspiracy. And the daughter of Geoffrey Francis Sullivan believes the pilot was jailed and eventually executed in Cuba. She claims he was seen alive as late as thirty years after the flight. In 2010 she sued Fidel Castro over her father’s death.

No-one knows what really happened. Occam’s Razor dictates that semi-amateur missions against a communist dictatorship in the wake of a failed coup and near nuclear war were never going to end well. Rorke was on borrowed time from the moment he set foot in Florida.

If you have any ideas about Alexander Rorke’s disappearance then share them in the comments below.

For more warlike weirdness, you can buy my  books in paperback or ebook:

Soldiers of a Different God: How the Counter-Jihad Created Mayhem, Murder, and the Trump Presidency [or amazon.com]


Lost Lions of Judah: Haile Selassie’s Mongrel Foreign Legion [or amazon.com]


Katanga 1960-63: Mercenaries, Spies and the African Nation that Waged War on the World  [or amazon.com]


Franco’s International Brigades: Adventurers, Fascists, and Christian Crusaders in the Spanish Civil War [or amazon.com]

2 thoughts on “Missing Over Cuba, $25,000 Reward

  1. I AM BRIAN RORKE,you wrote about my father,ALEX I RORKE, with out permission and false statements,no one notified me of you unacceptable work!this is so unacceptable work, just like unsolved mysteries!


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