His brothers included:[1] He matriculated at Exeter College, Oxford on 20 March 1607,[a] and was admitted on 1 February 1609 to the Inner Temple, where he was called to the bar in 1618.

He early identified himself with the popular party and was unsurpassed by any other member in his vigour to effect the impeachment of George Villiers, 1st Duke of Buckingham, and was likewise insistent that supply should be postponed to the redress of grievances.

About a week after the execution of King Charles I in 1649, he accepted on 8 February 1649, a new commission as Lord Chief Justice of the upper bench on the understanding that no change should be made to the fundamental laws of the kingdom.

[citation needed] On 13 February 1649, he was voted a member of the Council of State, which appointment strengthened the government, and his presence on the western circuit contributed much to the settlement of the public mind.

Don Pantaleone Sá, a brother of the Portuguese ambassador, was arrested for a murder committed in an affray in the New Exchange in the Strand, London.

The decision was without precedent, for it could neither be denied that the Don was of the household of the ambassador, nor that the privilege of exterritoriality had theretofore been understood to extend even to cases of murder.

[5] On the outbreak of the Penruddock uprising on 12 March 1654–5, Rolle was at Salisbury on assize business, when he was surprised by the cavaliers under Sir Joseph Wagstaffe, who coolly proposed to hang him.

[citation needed] He served as one of the commissioners for the trial of the insurgents at Exeter in May 1655, and being unable to decide against the merchant George Cony, who had sued a customs officer for levying duty from him by force without authority of parliament, and rather than give further offence to the Lord Protector Oliver Cromwell he resigned on 7 June 1655.