Gregory, born about 1520, was the only son of Thomas and Elizabeth Cromwell. Gregory’s two legitimate sisters died along with his mother of sweating sickness when Gregory was nine.

Thomas Cromwell sought to ensure his son’s well-being and education in the aftermath of his bereavement by sending him to nuns to be cared for. Cromwell knew many abbesses having gained a reputation as a man of business, legal advisor and arbitrator: an irony probably not lost upon the nuns when they were unceremoniously booted out of their homes. After Gregory outgrew the nuns Cromwell sent his son, aged about fifteen, to be educated in Cambridge where he worked hard according to the letters that his tutors sent Cromwell but without the gifts that Cromwell himself demonstrated for language and learning. It must have been frustrating for Cromwell, a self-made and apparently self-taught man, to see his son provided with the best education that money could buy but apparently lacked the skills to make most use of the education which his father provided.

One of the letters that Gregory’s tutor sent to Cromwell reveals a narrowly averted tragedy. Gregory’s room-mate accidentally set fire to his bedding and caused much damage but, fortunately, no loss of life. Cromwell was called upon to compensate the tutor for the loss of his possessions. Other letters cover more mundane affairs such as the need to feed a clothe the growing boy.

In a bizzare twist of fate Cromwell arranged for Gregory to marry Elizabeth Seymour in 1537– sister of Jane Seymour so was the brother-in-law of the man who had his father executed in 1540– Henry VIII. So technically Henry VIII was the uncle of Gregory’s children. Gregory did not suffer from his father’s fall from favour instead he went on to become a baron owning extensive lands in Leicestershire and in Rutland. He was created a baron less than five months after his father’s execution and would eventually regain some of the lands that the king had confiscated when Cromwell was found guilty of treason.

Gregory died in 1551 of sweating sickness. His letters demonstrate the depth of his affection for his wife and his children. There is no picture of him that is known. It is odd given the number of pictures of Cromwell painted by Holbein that none was commissioned of Cromwell Junior. There is however a possible picture of Elizabeth Seymour who went on to marry for a third time after Gregory’s death.