Shortly after being appointed Ambassador in 1957, Whitney acquired the Wentworth country estate. The diplomatic life gave him and his wife access to all that they enjoyed: the establishment; the celebrity; the jewels; the style; the sophistication; the art; the country estate; the horse racing; the golf.

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Ambassador Whitney, an American aristocrat, became deeply ingrained within English society, forming close friendships with figures including the Queen and Prince Philip, Princess Margaret and Lord Snowdon, and Prime Minister Harold MacMillan.

Whitney entertained extensively while in Great Britain, both in an official and personal capacity. After rapidly exhausting the embassy budget, he went on to use his own funds for the next four years.

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Through his travels across Britain and beyond, Ambassador Whitney saw the best of the best. After visiting the Prime Minister’s official country estate, he thought something similar would be a very desirable supplement to his vast official London residence. Whitney made his choice carefully. Money was not an issue but style, location and quality were paramount. He had noticed Cherry Hill some years earlier in a MoMA exhibition and saw it as a  great architectural statement and a complementary backdrop to his sculptures and treasured art collection.

Whitney retained the estate for nearly 30 years and, as Ambassador, used it for relaxing and lavish entertaining in a more intimate setting. On weekends, he would invite friends over for golf and during the Royal Ascot races he would entertain there afterwards. While away, Whitney would often loan the property to friends including Winston Spencer-Churchill. He took great personal interest in the property and commissioned landscaping, extensions and a newly built horse stable. Many of the paintings displayed at Cherry Hill were exhibited at the Tate gallery in 1960 as part of the John Hay Whitney Collection.