Mainly because of Henry Plant's connections in the War Department, Tampa was chosen as an embarkation center for American troops in the Spanish-American War. Lieutenant Colonel Theodore Roosevelt and his Rough Riders were among the 30,000 troops who waited in Tampa for the order to ship out to Cuba during the summer of 1898, filling the town to bursting and delivering another huge boost to the local economy.
The discovery of phosphate, the arrival of Plant's railroad, and the founding of Ybor City and West Tampa—all in the mid-1880s—were crucial to Tampa's development. The once-struggling village of Tampa became a bustling boomtown almost overnight, and had grown into one of the largest cities in Florida by 1900.
During the first few decades of the 20th century, the cigar-making industry was the backbone of Tampa's economy. The factories in Ybor City and West Tampa made an enormous number of cigars—in the peak year of 1929, over 500,000,000 cigars were hand rolled in the city.
In 1904, a local civic association of local businessmen dubbed themselves Ye Mystic Krewe of Gasparilla (named after local mythical pirate Jose Gaspar), and staged an "invasion" of the city followed by a parade. With a few exceptions, the Gasparilla Pirate Festival has been held every year since.
Beginning in the late 19th century,
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