Native New Yorker Henry Flager had a vision to connect the Florida Keys. With the experience of establishing the Standard Oil Company with John D. Rockefeller, he was able to become the wealthy and well respected businessman he is today. He turned his vision and dream to life in 1885 when he began a short line railroad from Jacksonville and St. Augustine to extend south toward Miami. The whole point of this railroad was to connect the deep port of Key West, later on it went way beyond. This railroad would benefit the growing amount of 10000 people living in the Key west city and the shipping commerce. He had even envisioned connecting Key west with Cuba. The development of the railroads took years with many interruptions like hurricanes which were quite devastating, along with being hit with the Great Depression. As we all know, The Great Depression caused lots of damage to the whole United States, the keys population decreased from 22,000 to 12000, and 80% of residents depend on government assistance. Therefore, Federal Emergency Relief Administration had to step in and give a hand to continue development and promotion of the beautiful attraction that is Key West, to increase tourism. It was not easy to accomplish but the hard workers were able to make Henry Flagers dream come true by the age of 82 when he first rode and witnessed that his dream came true from Homestead to Key West. The result was the Key West Extension, the largest deepwater port on Atlantic Coast.
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