–Up both Kettle Hill and San Juan Hill in Cuba in the Spanish–American War. He then rides his “hero” status right into the White House in September, 1901 via the vice presidency. His boss earlier in the first year of his White House stint, President William McKinley was assassinated after six months in office, springing ‘T.R.’ into the Oval Office. From San Juan Hill to the presidency of the United States within 3 years.