Cromwell was born into a wealthy family

Cromwell was born into the landed gentry into a family that was descended from Thomas Cromwell's minister's sister (his great-great-granduncle). On his father's side, the Cromwell family had a long history of wealth. Although he came from a wealthy family in Huntingdonshire, he belonged to a junior branch, and despite being a gentleman, he was not wealthy. They belonged to the group of people who owned a lot of land in the area. Since they benefited from Thomas' administration of the Dissolution of the Monasteries, his family amassed enormous wealth. Cromwell had a good life, but not one like the upper-class families. His education was also respectable.

Only four of his letters and a summary of a speech he gave in 1628 remain, so little is known about the first 40 years of his life. Oliver had to leave Sidney Sussex College in Cambridge when his father passed away in 1617 in order to care for the estate, his mother who had recently lost her husband, his wife Elizabeth, and ultimately their nine children. Financially, it was a struggle, but Oliver's luck changed after his uncle gave him leases on several properties in Ely, including the lease on the home he and his family moved into in 1636 and lived in for just over ten years. The obligation to collect the local taxes was included in the lease.