Winston Gray Character Analysis

In “Hope,” Winston Gray is Millie’s lover. He’s a young cane cutter from the rural region of Montego Bay, and he meets Millie toward the end of his work season when they cross baths on Kingston Beach. They fall in love and have sex just days before Winston is set to return home. Winston tells Millie he wants to have a future together and promises to write all the time, which he does—and he sends money, too. However, Willemina, having heard rumors about Millie and Winston’s dalliances and wanting to ensure that Winston doesn’t hold Millie back from building a better life for herself, intercepts the letters and hides them from Millie. In the meantime, Millie discovers she’s pregnant with Winston’s child and eventually gives birth to a baby boy, Eddison William. Winston, having not heard back from Millie, returns to Kingston after the baby’s birth. Initially Millie, not knowing that Winston has been sending her letters and money all this time, is irate, and she Winston and berates him for being a “lyin’ field bwoy.” But when Willemina ultimately gives in and presents Millie with Winston’s letters, the couple reconciles, and Winston expresses his desire to have a future with Millie in England. The story ends on an ambiguous note: just after Winston declares his desire for a future with Millie, he sees Eddison and recognizes that the baby is likely his. It’s not clear whether this discovery reinvigorates Winston’s desire to have a future with Millie—or whether, as Willemina seems to have feared, it will scare him off.