*Jim-related spoilers.*
I’ve written about Jim’s relationship with Oluwande, but I wanted to circle back and give them their own individual write-up as well. Although, like Olu, they’re less prominent in season 2 than they are in season 1, they’re an important character whose presence adds a lot to the show.
A major theme of Our Flag Means Death is figuring out who you are outside of expectations: regardless of what society, family, or friends think a person is supposed to be, it takes courage for someone to find the grace to carve out space for themselves as something different. Jim embodies that idea in more ways than one. As a child, their entire family was murdered by the Siete Gallos, and they were taken in by a nun who raised them to be a killer. To Nana, nothing was more important than Jim taking “God’s divine revenge” and avenging their family.
And for a long time, that’s what Jim lives for. They kill the first of the Siete Gallos, Spanish Jackie’s favorite husband, and then are forced to go on the run from Jackie, which is how they end up on the Revenge in the first place. Their knives are always at the ready, and they put themselves at serious risk to return to Jackie’s to recover their father’s dagger. They’re both ruthless and reckless, showing little interest in their own well-being.
But the more time they spend on the Revenge, the further away that quest seems. At sea, Jim grows closer to Oluwande, and by the time they find themselves back on St. Augustine, they’re forced to face Nana and admit they’ve only killed one of the Siete Gallos. Jim lets her shame them for this, and they try to push themselves back into a vengeance-driven life they’ve already started to cast off, giving up Oluwande in the process. It’s only after another confrontation with Jackie that they realize they can’t keep living for Nana’s revenge. They want more than that now, and it involves returning to the crew and Olu.
Jim further challenges expectations with their gender. Although they’re raised as a girl, they disguise themselves as a man when they go on the run from Jackie, and by the time their true identity is revealed, they’ve started to understand that they’re not really either. The crew doesn’t get it at first—“What kind of name is Jim for a lady?”, “Are you a mermaid?”—but Jim is prepared to be who they are without elaboration. “I’m gonna keep this very simple,” they say. “You all know me as Jim, ¿sí? So just…keep calling me Jim.”
Between affirming their gender and, even more significantly for him, putting their revenge quest to rest, Jim is able to feel surer and safer in who they are. Throughout much of the first season, they’re spiky and standoffish, a cynic in comparison with most of the Muppets in the crew. They’re not really won over by Stede’s softness, and they respond to most things with a sharp remark. But in season 2, Jim lets their guard down more. Even after being forcibly separated from Oluwande and made to crew for Ed during his Kraken era, they find ways to hold to hope and care, quite the contrast from their hard-edged season 1 self. They look out for and encourage others, helping those around them find strength and a bit of lightness during a frightening time, and once they’re back on the Revenge, they’re gradually able to unwind and just be. The Jim of season 1 would’ve never been instrumental in planning Calypso’s birthday, and they certainly wouldn’t have tried their own retelling of the wooden boy story to comfort an upset crew member.
It's certainly a big departure, and Jim’s reduced screentime in season 2 can make that feel a bit less purposeful than it could be. If (when???) we get a third season, I hope we get more time with them and can more clearly see the throughline of these changes in them.
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