Simon seemed destined for a seat in the Cabinet. However, after three years as Solicitor-General, he resigned from his office and his seat in Parliament in 1962, to widespread surprise, to become a High Court judge, and President of the Probate, Divorce and Admiralty Division, replacing Lord Merriman. His legal practice at the family bar had prepared him for this position perfectly. The year after taking office, he had an operation to remove a benign tumour. The operation left him paralysed on one side of his face: he had a speech impediment and also lost the use of his right eye; he habitually wore a black eye-patch thereafter, which gave him somewhat of a piratical air.