*Some Izzy-related spoilers.*
At this point, I’ve decided I’ll probably just do Favorite Characters posts for all the Our Flag Means Death characters I write about. I’m in far enough now that it would feel mean if I did, like, a dozen Favorite Characters write-ups and just two or three Character Highlight write-ups. So Favorite Characters for everybody! In the case of Izzy, I don’t adore him in the same way I do Stede, Ed, Frenchie, Roach, and so on, but he’s definitely a very interesting character.
Izzy has been sailing with Ed for decades, and for a good chunk of that time, it’s been as his first mate. When he meet him in season 1, he’s a severe little man who has a lot of ideas about what constitutes real piracy. Some of that is his general disrespect for “amateurs,” like Stede and the crew of the Revenge, but it’s also tied to his beliefs about masculinity. There are certain things that a pirate Simply Doesn’t Do, and in his mind, Stede embodies all of them. Ed becomes fascinated by Stede before they even meet, and once they do finally come face-to-face, Izzy quickly decides he has to get Ed away from him by any means necessary.
There’s the jealousy aspect, of course. Izzy appears to have some sort of unrequited love for Ed, and as the person who’s been Ed’s right-hand man for so long, it burns Izzy up to see his captain falling in so easily with someone Izzy considers to be a fool and a disgrace. More than that, though, it’s not Ed Izzy is in love with—not the real Ed. No, Izzy holds up and venerates Ed’s Blackbeard persona. That, in his mind, is what a real pirate looks like. When Ed is around Stede, he indulges in his softer side, enjoying Stede’s finery and being more emotionally open. Izzy views this as dangerous. He’s afraid of losing Ed, not just to a possible romance with Stede, but to Stede’s whole way of being.
Throughout season 1, Izzy is placed in opposition to Stede and Ed’s relationship, and more importantly, to Ed’s character growth. He doesn’t want Ed to change and tries to hold him where he is, even though Ed is very explicitly unhappy with his current way of life. At the start of the series, Ed is bored and depressed, understimulated because his infamy invites surrender rather than challenge. He’s desperate to get out from under the stifling identity of Blackbeard, and Izzy can’t have that. When he realizes Ed doesn’t really plan to go through with killing Stede, he tries to do it himself, challenging Stede to a duel. And when that doesn’t work, he hands the Revenge over to the literal enemy, the British navy, offering them the chance to execute Stede in exchange for remanding Ed into his “custody” (gross.)
Izzy holds on so tightly to what he thinks Ed is supposed to be, but that’s never who Ed really was. When Stede and Ed are separated at the end of season 1, Ed feels abandoned and heartbroken, and Izzy can’t abide that. Their subsequent confrontation spurs Ed to retreat deeper than ever before into Blackbeard. Izzy thinks this is supposed to be everything he wanted, but in truth, it’s more than he bargained for. The depressed Kraken-era Ed buries his vulnerability deep beneath his hard, ruthless Blackbeard persona. When Izzy displeases him, Ed cuts off one of his toes. He forces his crew into an endless grind of raid after raid, so much so that he’d rather dump their plunder in the ocean than let it slow down the ship. In desperation, trying to pull Ed out of this, Izzy suggests they talk it through, inadvertently invoking Stede. This sends Ed spiraling, and he ultimately shoots Izzy in the leg.
This is where Izzy’s character transformation really begins. He loses the leg due to an infection, at which point he becomes depressed and drinks heavily, wondering what good he’ll be as he fears he won’t be able to be the pirate he was. But the newly reunited crew of the Revenge bands together to help him out, constructing a prosthetic for him. Izzy is deeply touched by this, and although he maintains something of his edge, he isn’t the same bitter man as before, not beholden to the same prescriptive views of gender and vulnerability.
The show doesn’t delve much into Izzy’s motivations here, but I imagine it’s affecting to be met with compassion by the crew. The same people he mocked as not being “real pirates” are now supporting him, in spite of his past betrayals, and they’re offering to welcome him into their fold. As for Stede, he didn’t turn the crew into good people, but he made space for them to embrace that side of them with his gentler “talk it through as a crew” approach. Early in season 1, Izzy also seems to realize that Stede really does know and appreciate Ed, maybe even realizing that Stede understands the real Ed better than he does.
This growth allows Izzy to make peace with Stede and Ed getting back better. He doesn’t try to separate them any longer, instead making deadpan jokes about their sex life. And overall, instead of being so focused on micromanaging who he wants Ed to be, Izzy starts spending a little more time figuring out who he wants to be. This is shown most starkly on Calypso’s birthday, when Izzy dips a toe into understanding his own softer side—first, he has Wee John make up his face so he looks pretty, and then he serenades the crew with a gentle rendition of “La Vie en Rose.”
It's because of these changes in Izzy that he’s the one to give the money speech in the season 2 finale, quietly standing up to Ricky and staking claim for the pirates. In lieu of my usual collection of several great shorter lines from an Our Flag Means Death character, I’ll just include the whole speech here, wonderfully delivered by Con O’Neill:
“You don’t know the first thing about piracy, do you? It’s not about glory. It’s not about getting what you want. It’s about belonging to something when the world has told you you’re nothing. It’s about finding the family to kill for when yours are long dead. It’s about letting go of ego for something larger: the crew.”
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