The Winslows had both slaves and servants in their households. While slaves were black and held as property for life, servants were white and under contract to work for a shorter period of time. It is difficult to tell how many servants and slaves worked in their household. From a memorial to the commissioners investigating Loyalist claims for compensation, we know that Edward Winslow Senior arrived in Halifax in September 1783 with "three black servants" and Edward Winslow Junior mentions the names of several of his "servants" - Hector, Daphne, Mother Silk, Little George, Caesar, Frank, and Juba - in his letters.
What is clear from his correspondence is that the Winslows treated their white and black servants differently. In a remarkable letter to his wife, 18 September 1784, Winslow drew a sharp distinction between John Porter, a "scotch boy," whose training included the possibility of schooling, and his "Black boy" Frank, who was segregated because of his colour. While the documentary evidence is slight, the existence of black Winslows in New Brunswick who claim Edward Winslow as their ancestor suggests that he had sexual relations with at least one of his servants. In 1905 Martha Mathilda "Tilley" Winslow became the first black woman to graduate from the University of New Brunswick.
Elite Loyalists such as Edward Winslow held beliefs about class, gender, and race that were only beginning to be questioned in Europe and North America. In the eighteenth century, a rigid class hierarchy determined one's status in society and lower orders were expected to defer to their "betters." Patriarchy, the view that women and younger men were subordinate to older men, was widely accepted and racist thinking allowed black people to be enslaved, sexually exploited, and cruelly treated.
The views of Edward Winslow and his friends took root in New Brunswick with devastating results. In his eagerness to create a "Gentlemanlike" colony, Winslow seems to have given little thought to the fact that he and other Loyalists displaced Aboriginal and Acadian peoples living in the lower reaches of the St. John River Valley in 1783. Women were excluded from political rights in New Brunswick until the twentieth century and racist attitudes prevailed long after slavery was officially abolished in the British Empire in 1834.
Not all Loyalists in New Brunswick shared Winslow's values. Included in the Loyalist migration were a number of Quakers who called for an end to slavery and supported equality for women. From the earliest days of settlement, the rank and file of Loyalist men questioned the right of a small elite to control the government and the patronage it dispensed. By the mid-nineteenth century political reform opened the door to wider political participation.