In April 1684 his widowed mother made a strong appeal to him to make suitable provision for her and her fatherless children, but to this he replied that, for the sake of peace, he had already conceded more than legal obligations required.
[1] On 2 October 1684 Montgomery was imprisoned and fined for harbouring covenanters, religious rebels,[2] and on 7 May 1685 he and his mother were pursued on account of conventicles held in his father's lifetime, but both pleaded that they were not responsible.
[4] He was chosen as member for the county of Ayr in the Convention of the Estates of Scotland which met on 14 March 1689, when he distinguished himself by his eloquent advocacy of the resolution proposed by Sir John Dalrymple, that King James had forfeited his throne and kingdom.
His ambition had already selected the office of secretary of state for Scotland, as that alone commensurate with his services and abilities; and when George Melville, 1st Earl of Melville, chiefly on account of his moderate opinions, was preferred, Montgomery, although offered the office of lord justice clerk, so deeply resented the supposed slight that he determined at all hazards to have revenge, and immediately set himself to organise a political society called The Club, the main purpose of which was to concert measures against the government.
[11] Some time afterwards he returned to London, and on 11 January 1694 was taken into custody, on the accusation of being the author of several virulent papers against the government;[12] but on the 18th he made his escape from the house of the messenger where he was confined, the two sentinels who guarded the door leaving their arms and going with him.