In 1961 Wolff joined Randolph Churchill's team of research assistants on the Official Biography of Winston Churchill project. The preface and acknowledgements describe him as in charge of research, but his own correspondence throws this supervisory role into doubt. The process of working with Randolph Churchill generated a considerable quantity of papers and had one on-going consequence in that after Randolph Churchill's death Wolff was one of the Executors of the Estate, which included the Biography amongst the assets. All the papers listed here relate either directly to work on the Biography or to the consequences of Wolff's association with Randolph Churchill.