Simon Bradstreet was the final Governor of the Massachusetts Bay Colony, which by 1686 had lost its charter. For over three generations the Massachusetts Bay Colony had inched increasingly further from English rule. Governors were frequently called to defend the Colony's charter to operate as a relatively independent company.

Bradstreet arrived in Boston with John Winthrop aboard the Arabella and over the next fifty years he served as an Assistant of the Massachusetts Bay Colony (a position comparable to today's Governor's Council), while representing Massachusetts in the New England Confederation for 33 years. Finally in 1679, he was elected Governor.

As English calls to revoke Massachusetts' charter grew, Governor Bradstreet took a conciliatory approach to England. Eventually all of New England's charters were revoked and together they were made in to the short-lived Dominion of New England. Bradstreet rejected offers to join the new government, which was maintained by Joseph Dudley until the arrival of the reviled Royal Governor, Sir Edmund Andros.

England's "Glorious Revolution" of 1688 disrupted Andros' rule, who was sent back to England in chains. The eighty-four year old Bradstreet found himself ruling again until the arrival of Massachusetts first Royal Governor, Sir William Phips in 1692.