We don’t really consider Henry VIII to have had friends, rather subjects, cronies and duteful wives and ministers of state. But Henry was a very sociable person and craved genuine relationships. Charles Brandon, the son of Henry VII’s standard bearer at the Battle of Bosworth, was to be his closest friend and companion for his entire life. They were educated together and Charles would hold a succession of important offices in the royal household. Henry VIII trusted Charles with some of the dirtiest jobs at the Tudor court, clearing out Katherine of Aragon’s household and later arresting and extracting a confession from Anne Boleyn. Henry also forgave him for marrying in secret his favourite sister, Mary Rose. Yet Brandon’s life was by no means free from misadventure. His marriage to Henry’s sister Mary was disastrous, and his relationship with Anne Boleyn fraught. He was accused of treason and was responsible for a military fiasco. Steven Gunn explains how Brandon not only survived these vicissitudes of fortune and managed to retain the king’s friendship, but steadily increased his own power, wealth and standing. Charles died in 1545, Henry ordered a lavish funeral and he was laid to rest in St George’s Chapel in Windsor where Henry had buried his favourite wife, Jane Seymour, and where he would end up himself a mere 18 months after his one true friend.