Robert Aske was a leader in the rebellion that followed church reforms enacted by England's King Henry VIII. When Henry broke from the Roman Catholic Church in order to divorce his first wife, Catherine of Aragon, he named himself titular head of what he styled as the Church of England. This meant that all property held by the Catholic church transferred to Henry. The Pope and other Catholic leaders naturally did not agree with this, but it was up to the local English people to protest and defend various properties, ranging from large, prosperous monasteries and convents down to tiny village churches.

Henry proceeded to seize such properties and all their wealth, giving it all to those to whom he owed favors, to his friends, and family. Part of the reason many English men and women were angry with Henry for this had to do with their piety. Most people during the period not only believed in God, but in a variety of religious superstitions. Furthermore, their own personal parish church was important on a social level. This is because most churches, monasteries, and convents served not only to nourish parishoners on a spiritual level, they also functioned as the only community social service for orphans, widows, the old, and the sick.

When Henry began dissolving these treasured resources, many people were furious and publicly protested. Robert Aske, who came from and old, well-to-do family in Yorkshire, was a lawyer, having served as a Fellow at Gray's Inn in London. He was also pious and mightily resented Henry's reforms. When he left London for his home in Yorkshire, the townsfolk and country people implored him to help lead a rebellion that had already begun. He agreed and helped to organize and lead what became known as the Pilgrimage of Grace. Later in the same year (1536), he was widely regarded as the "chief captain" of the rebellion.

Revolt was at that point wide-spread, and became a grave concern to the king. Henry sent messengers to speak with the rebellion leaders, and asked that Aske come to London for dialogue with the king. Aske was assured safe passage to London and back. He was also promised that the king would seriously consider ways to make peace with the rebels. The visit to London appeared successful, and Aske was on his way returning to Yorkshire when Henry ordered him arrested and returned to London. This rash decision was taken based on word that revolt had erupted yet again in the north.

Aske was housed in the Tower of London, later tried and convicted of high treason, and then returned to York to serve as an example of what could happen when one crossed Tudor rule. Aske was publicly hanged in chains. Despite film depictions of Aske as old and having a wife and children, or as a violent soldier, he was in his thirties when executed, having never married and with no children.