Olivia Winslow and her husband worked as corporate lawyers.
Present: Season ThreeEdit
June and the Waterfords travel to Commander Winslow's house. George's surrogate daughter, Polly, greets her father and the guests. She is joined by Winslow’s other children, who hug their father. Commander Winslow's wife Olivia greets the guests and introduces her children to the Waterfords. Serena holds the Winslows' baby in her arms.
Serena socializes with Mrs. Winslow, who says she is prepared to tolerate his vices. She tells Serena that she and her husband used to work as corporate lawyers and had no time for a family before the establishment of Gilead. Olivia also reassures Serena that she will have a family one day.
High Commander Winslow is killed by June at Jezebel's, with the body being disposed of by the Marthas at the establishment. Officially, Gilead considers Winslow to be missing, due to both the absence of a body and the recent arrest of Fred and Serena by American authorities in Canada.
After hearing of her husband's alleged disappearance, Olivia visits Eleanor Lawrence, accompanied by Naomi Putnam. She expresses concern that if her husband is not found, her six children will be taken away. Eleanor almost tells Olivia about June's plan to liberate children from Gilead; instead, Joseph clarifies that they will take the Winslow children in if George is not found. Olivia thanks Eleanor.