Dubliner on a royal mission in Cuba 250 years ago

As the Seven Years War came to an end, brigadier general Alexander O’Reilly planned to keep the English out of Havana

“Havana was a European city longer than any other in the western hemisphere and it still shows.” Photograph: Roxana Gonzalez/Getty Images

Brigadier general Alexander O’Reilly, the Dubliner who had quit his country and joined the Flight of the Wild Geese, had a great deal to do on a day like this in Havana 250 years ago this year.

As the Seven Years' War, which pitted the British and their Hanoverian vassals against the Bourbon monarchies of France and Spain, wound down, his mission was to take back for his master, king Charles III of Spain, that city and the swathe of Cuba from the English who had been occupying it for the previous 10 months. His head was buzzing with plans for new fortifications which would, he hoped, ensure that the island would never again be conquered by the English king George III or anyone else.

Charles III’s descendents were to keep it until the US seized control of the island from the 12-year-old Bourbon king Alfonso León Fernando María Jaime Isidro Pascual Antonio de Borbón y Habsburg-Lorena, otherwise Alfonso XIII, in 1898 as Cubans themselves were in revolt against the Bourbons.

Washington kept it for a while and made it one of its first colonial possessions outside North America.

New fortress
O'Reilly's plans took the form of the new fortress of La Cabaña at the entrance to one of the finest harbours in the Caribbean, years later to be the base of Che Guevara in the first years of Fidel Castro's revolution and within whose walls not a few counter-revolutionaries were to be executed.

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Though few tourists to today's Havana have much inkling of it, the island had a rich history long before Fidel's tough father Ángel immigrated here from the rocky Spanish province of Galicia, made good as a successful landowner and started a second family with his second wife, his former servant Lina Ruz. With his carefully shaven head Ángel usually carried a whip.

There are no streets or monuments called after Fidel Castro – yet. But Calle O'Reilly – which the Cubans pronounce O'Rayly – is one of the main streets of the Old Town, which commemorates the Dubliner. Apart from La Cabaña, the city has a wealth of military fortifications – El Morro, La Punta, La Real Fuerza, Atarés, not to mention the former Jesuit church, built of handsome coral stone, where Columbus's bones rested for a time and which became a cathedral when his majesty of Spain closed down the order in his dominions in 1767.

Havana was a European city longer than any other in the western hemisphere and it still shows. In the 19th century the Spanish business communities – the Basques, the Asturians and others – vied with each other to demonstrate by their buildings who was top dog. And that too still shows.

The Asturians, who made their fortunes in their ships which carried freight across the Atlantic, seem to have come out the winners and their palace, carefully restored by the government, is a still a monument to European regional pride and rivalry.

Fine collection
With five floors connected by marble staircases it today contains the finest collection of English and Scottish pictures in the New World with works by Kneller, Reynolds, Gainsborough, Romney, Thomas Lawrence, Raeburn and Joseph Wright of Derby, all the collection of Oscar Cinetas, a Cuban magnate who gave it to the state before the Revolution.

O’Reilly, who became field marshal, captain general and a count, married Rosa, the young sister of the governor of Cuba.