 He studied at Harvard College, graduating in 1765 with an MA.After graduation, as the political tension escalated between Great Britain and its North American colonies over issues such as trade, taxation, and governance, Winslow publicly put his support behind Massachusetts Governor Thomas Hutchinson and helped create "a company of Tories" in an effort to keep the peace.By 1774, Winslow was forced to flee Plymouth, and in April 1775, as a member of the British Army, he was involved in a bloody confrontation at Lexington against the Patriot militia.