North Korea and Cuba enjoy warm relations, with Kim writing an emotional tribute to Fidel Castro following his death last year.
And now Kim Jong-un has sent another letter to the island nation, which was badly hit by Hurricane Irma last week.
The tyrant expressed his condolences to Raul Castro after 10 people were killed and £1.67 billion worth of damage was caused in the country by the Category 5 hurricane.
The letter from Kim was also published by a Pyongyang-based propaganda newspaper.
He said: “Receiving the news of the causalities and losses of many materials caused by the recent hurricane in the eastern and central areas of your country, I extend deep consolation and sympathy to you and, through you, to the Cuban government, people and residents in the afflicted areas.”
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A direct message from Kim himself, rather than a note sent through a spokesman or other government official, is rare.
This is only the third time the pot-bellied ruler has put his own name to a letter of condolence, following messages to Fidel in 2012 following another hurricane and to Syrian dictator Bashar al-Assad after the Syrian’s mother died last year.
North Korea’s relationship with Cuba is an unusual one, with the two enjoying close relations despite a huge geographical distance.
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Last year Kim made a gushing tribute to Cuba following the death of leader Fidel and ordered three days of morning in North Korea.
Kim said Fidel was a “close friend and comrade” as he signed a book of condolences at the Cuban embassy in Pyongyang.
As three days of official mourning began, the despot said the country had been overcome with “deep sorrow”.
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In a statement, the ‘Supreme Leader’ said: “Castro made all efforts to strengthen the friendly and cooperative relations between the two parties, governments and peoples of our two countries and extended firm support and encouragement to our efforts for national reunification and just cause with the invariable revolutionary principle and obligation for over half a century.”
In a separate editorial in a Pyongyang-based propaganda newspaper, Kim said Cuba was now a “shining success” thanks to Fidel’s influence.
The opinion piece read: “The Korean people are overcome with deep sorrow together with the revolutionary Cuban people and expressing deep condolences to the party, government and people of Cuba and the bereaved families over his demise.
“His demise is a great loss to the Cuban people and the progressives of the world struggling for socialism and justice.
“Fidel Castro Ruz is a revolutionary fighter as he built the first socialist system in the Western Hemisphere of the earth and devoted his whole life to the prosperity of the country and its people’s happiness.
“The shining successes the Cuban people have made in socialist construction are directly linked with his name.”