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So I got bored... Again.
My headcanon for Bessie is that She was an orphan who worked in the factories just to get by. She eventually had to quit her job in her 30s due to her health rapidly deteriorating, which led to her moving out into the middle of the woods. Her health made a recovery being away from the factory, and she started to write books about research she did on America's wildlife to get some money, but eventually decided to live a life constantly moving from one place to another, living off the land while documenting new things she discovered. She was especially interested in birds. I imagine one day She was just minding over own business at her campsite in the Grizzlies, when Hosea suddenly rides by, being chased by some bounty hunters. And Bessie offers to help hide him until the bounty hunters leave.
She wasnt in the best health, but she thrived out in the wilderness, away from society. And was the sweetest person to be around.
Hosea and Bessie were 100% the sweetest couple.... the sweetest couple who is very capable of either robbing you of everything you have or killing you.
So I got bored-
My silly little headcanon is that Annabelle was from a rich, french family. But ran away to America at 16 when her family(mainly her father) was insistent she marry an old man of wealth, stealing a good chunk of her family's money before she left.
In America, Annabelle became infamous for her robberies. She'd dress like a woman of high standard, waltz into banks, hop on trains, stop stagecoaches, and act like any proper lady when announcing that she was infact robbing the place. And ofcorse when no one listened, they sure as hell will once they witness Annabelle blow someone's head off. Her main weapon of choice was a shotgun she built into a parasol to disguise it. But she had plenty of other weapons, such as a knife and revolver sitting in straps on her legs, a twist off mechanic for the parasol's handle that reveals another knife, her heels on her boots have razors embedded in the back, she was decked out at all times.
Annabelle found her success by defying society's standards when it came to women, and using it to her advantage.
Dutch and Annabelle Van Der Linde were a batshit insane couple, and I am here for it.