Richard "Dicky" J. Bolles

Richard J. Bolles (August 1, 1843 – March 25, 1917) was born in New York City and was given the nickname, "Dickie" because of his 5'6" height. He has been described by various sources as the Napoleon of Finance, and a land swindler. which he held for many years.

Colorado Bolles went west in 1885 for business opportunities in Aspen, Colorado. In 1890 he settled in Colorado Springs where according to his obituary, "At one time he owned in Colorado what was said to be the richest silver mine in the world, his holdings there netting him $6 million." Agnes W. Cain was a shrewd Cleveland businesswoman, age 36, who became his secretary during his successful Colorado mining days. After a time, private detectives arrived in San Francisco to investigate Madam Bizette. She was aware of everything but offered no explanation. Sometime later, she announced that she was going east, and she was gone.

Florida In 1907, Bolles was invited by Florida's Governor, Napoleon Broward, to assist in draining Everglades and developing the area around Miami. The following year Bolles and investors from Colorado Springs founded the Florida Fruit Lands company and purchased of undeveloped land for $2/acre from the Florida Internal Improvement Fund with the stipulation that 50% of proceeds from land sales would be used to drain Everglades land.

His sales pitch was ultimately a scam and the truth eventually was revealed. In 1911, unhappy customers brought suit against him. In 1913 he faced trial but claimed that his salesmen misrepresented the land sold due to being "misled by officials of the State of Florida and officials of the United States Department of Agriculture."

On March 26, 1917, Bolles collapsed on Florida East Coast Railway Train 86 en route from Palm Beach to Jacksonville. Members of the Boston Red Sox from the American League Baseball team were travelling from Miami to Macon in the same sleeper car. They attempted to save him but were unsuccessful. Cain had been in Jacksonville for nearly ten years and was well established in local real estate and investment circles. A young Roger Painter began working for Bolles in 1916 for $4/week doing office jobs. After working together for several years, Agnes and Roger hit it off and were married early 1923 Mr. & Mrs. Painter moved into the foreclosed former hotel before it was leased to the Florida Military Academy.

In 1983, George Hallam, an English Professor at Jacksonville University wrote the book, Bolles: The Standard Bearer. In it, Hallam quoted from Richard Bolles' journals: "I am in nearly every business and social transaction guided almost entirely by impulse, with no fixed principles."