The wealth of the Cholmondeley family was greatly enhanced by Cholmondeley's marriage to Sybil Sassoon (1894–1989), a member of the Sassoon family, a Jewish banking family with origins in Baghdad and India, and heiress to her brother Sir Philip Sassoon.
Sir Philip served in the First World War as military secretary to Field Marshal Sir Douglas Haig and, during the 1920s and 1930s, as Britain's undersecretary of state for air.
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The family name of Sassoon, is also commonly shared by many Armenian and Kurdish families and tribes who all originate from the mountainous district of Sason (whence the family and tribal names), west of Lake Van, in upper Mesopotamia, in modern Turkey.
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With two of his brothers he later became prominent in England and the family great friends of the Prince of Wales, later Edward VII.
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Long involved in finance, commerce, and the law, they are considered to be one of the principal families in the "cousinhood" of senior sephardic Anglo-Jewish families, the de facto Anglo-Jewish aristocracy: these influential families of the "cousinhood" include the d'Avigdor family, Sassoon family, Goldsmid family, Henriques family, Kadoorie family, Lousada family, Mazza Family, Montefiore, and Samuel family.