Rhys Darby and Taika Waititi in key art for 'Our Flag Means Death' season 2

The Real Stories Behind the Pirates of ‘Our Flag Means Death’

Season 2 of Our Flag Means Death is exceeding all expectations. Created by David Jenkins, the Max series takes inspiration from historical pirates and casts them in a new light. Rhys Darby’s gentleman pirate Stede Bonnet and Taika Waititi’s Edward “Blackbeard” Teach (and their interesting relationship) are based on real people. So are Israel “Izzy” Hands (Con O’Neill) and season 1’s John “Calico Jack” Rackham (Will Arnett).

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The depictions may not be 100 percent accurate, but they aren’t exactly inaccurate either. Historical records from this period are varied, skewed, and severely lacking. So we can’t say without a doubt who these people were or how they acted. Since pirates were considered by criminals by their contemporaries, depictions of them would not have been favorable. Also, many accounts may have been sensationalized to sell newspapers and books. Mentions of overt queerness or women not fitting prescribed social standards might have been left out of any recorded text. Pirates are also a group that didn’t leave much in the way of primary sources. Not many pirates kept journals or held extensive correspondence, so many of these accounts come from word-of-mouth from supposed witnesses.

Our Flag Means Death takes these figures in a direction that is fresh and adored by fans. The show became an unexpected hit for pirate lovers everywhere. It only makes sense that the hit queer pirate show would bring in more historical figures for season 2. Let’s look at all the infamous pirates that have been given a new lease on life in OFMD.

Zheng Yi Sao

Ruibo Qian as pirate Zheng Yi Sao in 'Our Flag Means Death' season 2

Zheng Yi Sao is considered to be one of the most (if not the most) prolific pirates in history. Although the real Zheng Yi Sao sailed long after the other pirates featured in the show, she’s a great addition to the cast. Introduced as “Susan the soup merchant” and played by Ruibo Qian, Zheng Yi Sao reveals herself to be a pirate queen early on in the season. As in real life, she commands a fleet of ships with a tight crew. During her reign over the seas near China, Zheng Yi Sao led over a thousand ships and personally commanded over 200 ships along with their crews. Her pirating days ended after negotiating her surrender to the Chinese government, and she lived the rest of her days as a free woman.

John Roberts / Bartholomew Roberts, a.k.a Black Bart

Although he wasn’t called Black Bart (the pirate, not the Western outlaw) in the show, this notorious pirate made an appearance. While Stede Bonnet and Oluwanda accompanied Zheng Yi Sao onto a ship, they were told the captain was called John Bartholomew. In real life, this captain was more well-known by his aliases Bartholomew Roberts and Black Bart. The real-life version is credited as one of history’s most successful pirates, and overtook more than 400 ships. Some sources also credit Black Bart with writing a pirate code that ensures democracy and equality on ships. He also served as inspiration for the Dread Pirate Roberts in The Princess Bride.

Captain Benjamin “Ben” Hornigold

Blackbeard (Taika Waititi) and Captain Hornigold (Mark Mitchinson) in 'Our Flag Means Death' season 2

Captain Benjamin Hornigold was mentioned in season 1 of Our Flag Means Death, but we didn’t see him until the new season. Calico Jack and Blackbeard joked about how they met on the ship and mutinied against the captain. While in purgatory, Blackbeard sees Hornigold, who wants to go by Ben, as his guide in the unknown land. The real Hornigold was a pirate and may have had Blackbeard as his second in command when he sailed. He also was one of the pirates to establish a pirate settlement on the island of Nassau. When the King of England established a system for pardoning pirates, Hornigold saw the shift in the times and took the pardon and hunted his former pirates until his death.

Anne Bonny and Mary Read

Two pirate women smile in a room full of antiques in 'Our Flag Means Death.'

Anne Bonny and Mary Read have always been known as a duo; they sailed together and went to jail together. They were among the few women tried and convicted of piracy in their time. Some historians feel their story is very well documented via A General History of the Pyrates by Captain Charles Johnson. However, others—including myself—think the record falls apart under scrutiny. Luckily for those of us obsessed with this pair, OFMD featured them in episode 4 of season 2. They were a perfectly unhinged and chaotic couple of former pirates who open an antique shop.

Edward “Ned” Low

A pirate holds a violin bow while shushing in 'Our Flag Means Death.'

Ned Low (played by Bronson Pinchot) showed up looking to settle a score with Blackbeard. After Blackbeard broke his record of ships taken, Low had to get revenge and torture the other pirate. The show frames Low as a sadistic man who gets joy out of hurting and murdering other people. From several sources, it seems like the real Ned Low had the same hobby. The historical New Low didn’t have the musical connection as he did in the show, but he still was one of the cruelest pirates around. One account claimed he cut off a man’s lips, cooked them, and then made the man eat his own lips. Another story said he made a ship’s crew eat their captain’s heart. This guy was twisted. Unlike many of the other pirates, stories of his death conflict. No one knows exactly what happened to him. He may have been hanged, murdered, imprisoned, or died of old age. He probably wasn’t killed by Stede Bonnet, but who knows?

Hell-Cat Maggie

When Ned Low’s crew arrived in OFMD, one of them said her name was Hell-Cat Maggie. There are no pirates in recorded history with the name Hell-Cat Maggie. However, in the mid-1800s, a member of the Irish gang the Dead Rabbits had that name. She was an outlaw who fought against other gangs. In another life, she could have perfectly blended in as a pirate. Cameron Diaz’s character in The Gangs of New York was partially inspired by her.

(featured image: Max)

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D.R. Medlen
D.R. Medlen (she/her) is a pop culture staff writer at The Mary Sue. After finishing her BA in History, she finally pursued her lifelong dream of being a full-time writer in 2019. She expertly fangirls over Marvel, Star Wars, and historical fantasy novels (the spicier the better). When she's not writing or reading, she lives that hobbit-core life in California with her spouse, offspring, and animal familiars.