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Harry Slingsby was the father of Barbara Slingsby, the second wife of Sir John Talbot (1630–1714), MP. In 1655 he was implicated in a projected Royalist uprising in Yorkshire and was imprisoned in Hull. Oliver Cromwell decided to make an example of him and he was beheaded at the Tower of London on 8th June 1658. This portrait would have served as a private family memorial.

Sir Harry's 'Diary', kept between 1638 and 1648, not only gives a valuable account of the Civil War in Yorkshire, but also provides a vivid picture of the life of a country gentleman. In 1806 Sir Walter Scott published it in an abbreviated form, it was published in full in 1836.