After years of suffering in Gilead, The Handmaid’s Tale season 4, episode 5, “Chicago” gives June a major wardrobe change rife with several hidden messages. Outside of flashbacks, June has been depicted only in the clothes she is forced to wear as a handmaid in Gilead. Her red cloak is both an instantly recognizable staple of the show and a symbol of the oppression forced upon the wearer. When June finally reaches Chicago, which is outside the control of Gilead, she finally arrives in a place where her cloak can be shed in exchange for a new outfit — a change that is symbolic of her journey.

June’s new look is a stark difference from her Gilead attire. The red cloak and white bonnet are replaced by a plain yellow hoodie, jeans, and most importantly, a blue Chicago Cubs baseball hat. It’s the hat that offers the most significance for June, as it plays a role not only narratively in this episode, but is full of meaning for her character. June acquires her cap as a gift from Janine as the two get ready to part ways. Janine had actually gotten the hat earlier in the episode as a gift for Steven, the leader of the resistance group the two on the run handmaids were reluctantly taken in by in the previous week’s episode. It’s revealed in The Handmaid's Tale season 4 that Janine and Steven were romantically involved and that she had become somewhat infatuated with him despite June’s disapproval. In order to get the hat, Janine tries to trade her handmaid’s cloak for it; when that is not enough, as a show of good faith to her friend, June offers up her cloak as well, and the seller agrees to make the deal. 

Related: The Handmaid's Tale: Why June Says She Should've Left Janine Behind

This seemingly innocuous moment of bartering in "Chicago" is actually one of the key moments of the entire The Handmaid's Tale series to date. June and Janine have just traded in the clothes most closely associated with Gilead for something that is associated with the old United States that they spent most of their lives in. As much as the red cloaks of handmaids are instantly recognizable as something from the oppressive religious culture of Gilead, a baseball hat is a clear cultural product, and therefore symbol, of the former United States. Baseball has been called “America’s game” and “the great American pastime”; it's a sport that was born in the United States and has been shared by generations of Americans. In helping to get this hat, June is literally trading away a piece of Gilead for a piece of the United States.

The Handmaid's Tale Gilead Map

The fact that June wears a Chicago Cubs hat is also significant, and it relates to her journey in The Handmaid's Tale. The Cubs for most of their history were a downtrodden, cursed franchise. For a span of 108 years, they were never able to win a World Series, becoming the ultimate underdog in the sports world, until in 2016 when they were able to break through and win the title. June in that same way is the ultimate underdog: Everything June experienced in Gilead was designed to keep her down under the yolk of authoritarian oppression. She’s suffered indignity after indignity, often taking two steps back for every step forward in her quest to destroy or flee Gilead. The Handmaid's Tale has been building up these tragedies to make June’s hopeful final victory all the more meaningful — just as it was for the Cubs team, whose long period of failure made their 2016 World Series win all the more powerful for fans.

As "Chicago" comes to a close, it becomes clear that June has just taken a significant step towards freedom and revenge. She, along with her hat, were badly damaged by bombs sent from Gilead, but there is light at the end of the tunnel. June is still standing, continuing to battle in an insurmountable fight. Right before the credits roll, a beaten-down June is reunited with her best friend Moira, offering a small victory in a moment of chaos. If the Cubs hat is any indication, The Handmaid's Tale is setting June up to be a victor against all odds — and June appears to have finally arrived at freedom’s doorstep.

Next: Handmaid's Tale Season 4 Episode 5 Ending: What [SPOILER] Finding June Means