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Kitty and Derek Spence loved to entertain and built High Hope Estate with hospitality in mind. The guest book is full of notables who have enjoyed the splendor of High Hope; Charlie Chaplin, Ian Fleming, Noel Coward, Max Lerner, Agnes De Mille, Kurt Vonnegut, Adlai Stevenson and Richard Helms, to mention a few. Their circle of friends came from all over the world to visit in Jamaica.  Marilyn Monroe and Arthur Miller had dinner at High Hope  with Kitty while on their honeymoon to Jamaica in 1957.  They also had a flat in London, a home in Switzerland, and an apartment on Park Avenue in New York. They enjoyed the company of politicians and the literary crowd.

Kitty was a beautiful and fascinating woman. In her youth she posed for the famous American artist Maxfield Parrish. The extremes of her personality are seen throughout the property. For example, Kitty had Great Danes and Chihuahuas. She was married four times; Derek was her last husband. Her second husband was Robert Lehman of the Lehman Brothers banking family who was one of the richest men in the United States during the mid-30s. Kitty's grandfather was William Jennings Bryan William Jennings Bryan, known as "TheGreat Commoner", was a three-time Democratic candidate for president and served as Secretary of State under Woodrow Wilson.  Kitty's mother was the first woman ever appointed as an Ambassador from the United States in the 1930s.  Her appointment was to Denmark. It was actually Kitty's mother who introduced her to Jamaica, which Kitty came to love.

Derek was an English gentleman whose family had a monopoly on the mining of alum in the mid-1800s for the entire British Empire. Alum was mined for dental use and holding colors fast in fabrics. While Derek, better known as Derry, was chairman of the company which his grandfather had started, his true interest was in horticulture. While in England, Derry worked with lilies, but upon moving to Jamaica noticed that only three common varieties of hibiscus were to be found. He established a full scale nursery, still in operation, and from the red, white and yellow common hibiscus, developed over 560 varieties of hybrids. Today, High Hope still boasts one of the largest collections of hybrids in the world. Derry was known in Jamaica for his philanthropic work and Kitty as an eccentric, fun loving lady. She once had the pool moved from the upper level where the house sits to a lower level of the property because she enjoyed swimming in the nude and did not want to offend her guests. Derry died and was buried in Jamaica. Kitty, who earlier was invited to be an honorary member of the Mohawk Indian tribe, died of natural causes, was cremated and her ashes were scattered over the sacred burial grounds of the Mohawks in upstate New York.

Over 200 years ago, this property was the site of a retirement home for British Military officers. Before that, there is evidence that the indigenous people of Jamaica, the Arawak Indians found the property to be a useful vantage point (550 ft. elevation) ideal for observing approaching ships. It is fair to assume that the Arawaks were standing in the very place where the villa of High Hope now stands when they saw Christopher Columbus' ship arriving in Jamaica in search of the new world.

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