November 21, 1857 - Estrada Cabrera

His twenty-two-year grip on Guatemala was maintained through surveillance, political assassination, and the systematic elimination of rivals — making him one of the longest-ruling dictators in Central American history. The concessions he granted to the United Fruit Company reshaped the country's economy and sovereignty in ways that outlasted his regime by decades, laying the groundwork for what critics would call a "banana republic." His rule became a template for the region's subsequent authoritarian governments.

From Wikipedia

Manuel José Estrada Cabrera (21 November 1857 – 24 September 1924) was the President of Guatemala from 1898 to 1920. A lawyer with no military background, he modernised the country's industry and transportation infrastructure, via granting concessions to the American-owned United Fruit Company, whose influence on the government was deeply unpopular among the population. Estrada Cabrera ruled as a dictator who used increasingly brutal methods to assert his authority, including armed strike-breaking, and he effectively controlled general elections. He retained power for 22 years through controlled elections in 1904, 1910, and 1916, and was eventually removed from office when the national assembly declared him mentally incompetent, and he was jailed for corruption. As such, he was the longest-serving leader of Guatemala.

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