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| 1999, Jan |
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| Barbados prime minister Owen Arthur, whose administration helped the unemployment level in Barbados drop from 22 percent to 11 percent, was reelected by an overwhelming majority to the head of state position. The Labor Party of Barbados took 26 of 28 seats in Parliament. | 1 |
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| March |
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| The Antigua and Barbuda Labor Party won its sixth consecutive victory in parliamentary elections. However, in April Antigua and Barbuda's offshore banking industry was disrupted by warnings from the United States Treasury that lax procedures on the islands were making Antigua and Barbuda's banking industry very susceptible to money laundering. | 2 |
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| Aug. 11 |
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| Guyana president Janet Jagan of the People's Progressive Party (PPP) faced civil unrest in the opposition People's National Congress (PNC) and resigned her position for health reasons. The two parties were divided mostly along racial lines, the PNC being composed primarily of blacks and the PPP of East Indians. Jagan's replacement was 35-year-old Bharrat Jagdeo, who became the youngest head of state in the Western Hemisphere. | 3 |
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