I first became aware of Cutlass Liz in the movie The Pirates (2005). I was interested in the character, because the movie features a lot of other historical figures (ripped entirely out of time, mind) from Black Sam Bellamy to Queen Victoria. Liz, however, was a pirate I’d never heard of. But since the main characters in the movie are all (very) fictional, it didn’t bother me.
Then I did some research.
The legend of Elizabeth Shirland goes back quite a ways. It should, because Cutlass Liz began her career in the earliest days of piracy. The story goes that she was born in Devon the most sea-going of English counties, sometime between 1550 and 1560.
For reasons known only to herself, she decided while in her early teens that she was not going to live the life assigned to her. The story says that she disguised herself as a man (easy to do with the baggy clothes of the day) and went to sea as a sailor.
By 1577 she had enough experience to join the crew of the Golden Hinde and sail under none other than Frances Drake, the king of the Buccaneering Pirates. Drake was just embarking on the voyage that made his fortune – a round the world trip, with stop-offs to raid Spanish shipping and towns all over Central and South America.
Drake brought back so much gold that he became a legend. He had been backed in this endeavor by Queen Elizabeth I, and brought back so much gold that the queen’s share paid off the national debt. Elizabeth didn’t share in this acclaim, but she did get hooked on a life of adventure and piracy.
Elizabeth next turns up with her own ship – perhaps the result of the huge share of plunder that a sailor working for Drake would have received. She headed immediately for the Spanish Main, where she tried to live up to Drake’s legacy. She was very successful as a pirate.
However, according to legend, she also began to live openly as a woman, and to take lovers from among her crew. This led to trouble. Apparently some of these men tried to take over, and Liz earned her nickname by running them through with her trusty blade. This, in turn, led to more trouble.
Finally one of her lovers decided that he needed to get rid of her altogether. He betrayed her to the Spanish, who broke in on the two of them in the act. Elizabeth was dragged naked and screaming to the deck of her own ship, where she was summarily hanged. She did, however, murder her betrayer/lover with one last thrust of her trusty blade before she was dragged to her death.
There are reasons to believe that this story is true. Women did disguise themselves as men and go to sea. And anyone who survived Drake’s circumnavigation of the globe would have had more than enough money to buy a ship outright. It’s also believable that, owning a ship and captaining it herself may have given a woman enough confidence to think she could reveal her sex without consequences. That this wouldn’t work out for her also seems entirely believable.
However, the story has its flaws. Historians have identified an Elizabeth Shirland who married, had one child and lived her life quietly in Devon, never going to sea at all. But Elizabeth was one of the most popular names in England at the time, and Shirland was also quite common. There may have many women with similar names.
Another point against the legend is that “Liz” was not a common nickname for Elizabeth at the time. “Bess” was far more popular. (We can mitigate this by noting that the name "Liz" was used, but it seemed to have indicated a low sort of woman.) Also, the word “cutlass” was not in common use. The type of sword later called a cutlass was more commonly called a “hanger” because it hung off the belt. So “Hanger Bess” seems a more likely name.
It’s also pretty obvious that Liz’s behavior and fate seems to indicate a certain amount of male wish fulfillment.
Another piece of the story is even more far-fetched. This rumor says that Liz was a member of the lost colony of Roanoke. Captured by hostile natives, she lived with them for a while as a slave, then stabbed her owner with his own knife and escaped. She was picked up by the Spanish, then rescued by Drake just in time to go on his historic trip.
This seems far too unbelievable to be true, and is further discredited by the fact that we have a complete list of the Roanoke colonists, and she wasn’t one of them. In this version of the story, she also wins mountains of gold that far outshine those brought back by her mentor.
We’ll probably never be sure of the truth in all this. I see a person who may very well have lived, and who became a nexus for any bits of fiction that sailors cared to attach to her. Someone wanted to tell his “Cutlass Liz” story when other people were discussing Roanoke, and modified the tale accordingly. Someone else was talking about Drake’s mountains of treasure, and someone else wanted to out-do him.
I find this far the most believable version of events. But you can make up your own mind.