At San Juan Hill, 1100 Spanish soldiers were ordered to hold San Juan hill against an American offensive on June 1, 1898. For reasons still not quite clear, Spanish General Arsenio Linares chose to hold nearly 10,000 Spanish reserves in the city of Santiago and failed to reinforce his position. Despite this, the struggle lasted for more than twelve hours, and cost at least four hundred American and untold numbers of Spanish lives. During the engagement, Theodore Roosevelt became famous for his bold "charge up San Juan Hill".
In truth, Roosevelt was actually responsible for capturing Kettle Hill, one of the smaller heights in the vicinity, but the error (since attributed to a newspaper reporter) stuck.
See also: El Caney
In New York City, 'San Juan Hill' at the turn of the 20th century was an enclave of rough tenements in the West 60s, scene of pitched battles between the largely black residents and platoons of 20th Precinct police; the neighborhood was later razed to make room for Lincoln Center.
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