With hindsight, it is clear that Sherewood's election as mayor in 1641 was just the first in a series of disputed elections. The decision to abandon succession by strict seniority proved to be a fertile basis for factional intrigue. None of the mayoral elections over the next five years went entirely smoothly and, in some cases, even the corporation minutes struggled to disguise the extent of the disagreements. But none of these disputed elections was ever quite the same. All sides were to be skilled at finding permutations on that initial argument. There were to be several devious twists and turns along the way.

The election of Sherewood's successor in August 1642 was overshadowed by the wider political crisis. When the members of the Cambridge corporation assembled on 16 August, only the most optimistic or most naive could have assumed that a civil war was not about to start. Over the summer both the king and Parliament had begun to raise men, money and arms as precautions against a conflict that seemed increasingly imminent. Four days earlier Charles had announced that he would raise his standard at Nottingham on 22 August.

Cromwell for his part had already made sure that Cambridge was in the vanguard of the military preparations on the parliamentarian side.