Prince Henry was the first Royal prince to be educated publicly, attending St. Peter's Court School in Kent and then Eton College. His elder brothers had attended the Royal Naval College in Dartmouth, but Prince Henry went to Sandhurst before joining first the King's Royal Rifle Corps and then the 13th Hussars, moving on to the 10th Hussars. He greatly enjoyed sports whilst at school and was an noted huntsman and shot. Throughout his military career he represented the King at a number of events including investing the Emperor of Japan with the Order of the Garter and the coronation of Emperor Haile Selassie.

In 1935 he married Lady Alice Montagu-Douglas-Scott, the daughter of the Duke of Buccleuch and they acquired the Barnwell Manor estate near Peterborough. He fought during the Second World War and became the first Royal Governor General of Australia in 1945. In the years of his brother's reign, and those of his niece, Queen Elizabeth II, he represented the monarch on many occasions including the independence of Ceylon, now Sri Lanka. He died in 1974 and following the death of his widow, Princess Alice, Duchess of Gloucester many of his possessions were sold at Christie's in a landmark sale held on the 26 and 27 January 2006, which included this waiter.