Esther Williams (EW) was born into an artistic circle; an accomplished painter in her own right, her mother, Esther Baldwin Williams (EBW), was a student, studio mate, and later patron of Maurice Prendergast. EBW frequently corresponded with her mentor and friend, whom she also hosted as a guest at both her Annisquam and Boston houses. As the numerous works by Prendergast in the Williams family collection attest—including the two sketches on view here—EW was immersed in the American master’s insightful portraiture and evocative landscapes throughout her childhood. One of Prendergast’s visits with the Williamses is commemorated by another painting donated to the Addison by EW, Annisquam Beach (1907-10), bearing the inscription: “To my friend Oliver Williams,” EW’s father. Moreover, sittings for portraits by Prendergast of both her mother and her nurse, Annie Sargent Jewett, took place at the Williamses’ home and would have likely been witnessed by the young EW. These two portraits demonstrate the subliminal, if not formal, influence that Prendergast’s treatment of his subjects had on EW during the formative years of her aesthetic development.