5. Osbourne Fleming
Osbourne Berrington Fleming (born February 18, 1940) is a politician and a former chief minister of Anguilla. He held that post from March 6, 2000, three days after the Anguilla United Front, a conservative coalition which included Fleming’s Anguilla National Alliance won parliamentary elections, gaining at least 4 of the 7 seats, until February 15 2010 in which he retired from his seat as the chief minister of Anguilla.
Mr. Fleming was a prominent and successful businessman prior to entering politics.
He served for many years as Minister of Finance before winning election as Anguilla’s Chief Minister.