Includes: an illustrated letter from Jack to Peregrine Churchill from [?] the Western Front, and letters and postcards from Jack to Peregrine on subjects including Peregrine's dislike of school, a story about Peregrine's schoolfellow John Amery, a visit to the Canadian Rockies and the United States, particularly San Francisco, a stay with William Randolph Hearst, a dinner in Hollywood with Charlie Chaplin and Harold Lloyd, financial matters, sending up food as the shops in London were empty, and a wedding present for Mary Churchill [later Mary Soames]; letters from Peregrine to Jack on subjects including his hopes for the university and college entrance exam for Trinity College [University of Cambridge], studying engineering and his dislike of Harrow. Also includes letters from Peregrine's teachers and invoice and receipt for the removal of Jack's effects from 54 Berkeley Court, London, after his death.

Includes typewritten transcripts of the letters prepared by Celia Lee, filed next to the originals.