Bahrain’s Sheikh Khalifa bin Salman al Khalifa, the world’s longest serving prime minister and a staunch ally of neighboring Saudi Arabia and the United States, has died, the royal palace announced on Wednesday.

Sheik Khalifa, a dominant figure in the Gulf island’s politics for much of his near half century in power, passed away on Wednesday morning at Mayo Clinic hospital in the United States, Bahrain’s state news agency said.

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