Bonus video! How gay were pirates REALLY?

So one reason why it might, hypothetically, have been more likely for pirates to have gay relationships than other men was that pirates were already living outside the law, and would be hanged if caught, so they would have no reason to fear any extra legal penalties. After all, what would the forces of the law do if they were found out, hang them twice? Also, just to add to what you were saying about Olaudah Equiano: he was writing that in a published memoir, so it seems at least a bit unlikely that he would even hint at having had a relationship that would have got him killed if anyone found out about it. Given that the memoir was intended as an anti-slavery tract, it seems more likely that he was basically saying, "See, a black boy can be close enough friends with a white boy that they sleep in each other's arms; doesn't that prove that black people aren't actually subhuman and that maybe you guys should stop enslaving us?"

Recent "post-gay" theories about historical gays. Before gay identity arose in the 19th century, male same sex sex was often seen as something you did, not something you were. It didn't identify you. Same sex relations were usually older, richer, powerful males having relations with younger, poorer, less powerful males, through preference or availability. The shocking part for the public was often which male took the female's assigned passive part, not the inappropriate age of the male taking this part (Separate childhood as we know it, another Victorian innovation, hadn't quite been invented yet.) This violation of gender roles is where moral outrage was usually directed. Obviously there were adult male couples -- James I, Baron Von Steuben, etc. But this gives some insight about what might have been happening on board those all-male pirate ships and others, how they saw it, and how hard it is to compare it to what many gay men experience today, committed romantic relationship with your equal, which some academic indicators suggest is beginning to change again. Herman Melville, married with kids but bi or gay, offers a more recognizable 19th century view of possibly gay sailors, as in "Moby-Dick" (it's in the title!) and "Billy Budd."

Interesting... I'll have to watch OUR FLAG MEANS DEATH. And I must say, I LOVE that T-shirt, Matt. 😉

One thing that I think you overlooked was looking into the few female pirates who were around during the Golden age of Piracy. If you did, you would have probably would have come across the story of Mary Read and Anne Bonny, who were both real-life Pirates of the Caribbean, serving under pirate captain John Rackham in 1720 as they attacked ships across the West Indies. The pirate ship was captured in October 1720, near Jamaica, and all the male crew was executed while Read and Bonny were spared death by "pleading their bellied" (i.e. saying they were pregnant). Read died of illness while still in prison a year later, while Bonny was released and likely lived the rest of her life quietly in Jamaica. While Read and Bonny did reportedly did adopt male personas while pirating, there's no proof that either were actually trans (as we would understand that terms today), or if they were lovers. However, there is compelling evidence that they were at least close friends, and that when their pirate ship was under attack, it was these two who were first on deck, fighting side by side, and as hard (if not harder) than any of the other male pirates. During their trails they were described as "wearing men's jackets, and long trousers, and handkerchiefs tied about their heads: and ... each of them had a machete and pistol in their hands and they cursed and swore". Their potential romantic relationship has been long theorized though, and there's a pretty beautiful statue of the two of them called Inexorable, that sits near Execution Dock in London which celebrates their lives and fiery spirits. All this to say, if people loved what our Our Flag Means Death did for Blackbeard, then it's high time they make a similar show giving these two their due.