1-Stand and deli-whoops!
The few robberies that this highwayman has tried to carry out have been a disaster. The first time he tried to hold up a coach with an ancient double barreled shotgun, but when he pointed it at the coach driver, both the barrels fell off and the driver sent his coach galloping away. Next, he tried to hold up a coach with a flintlock pistol, but it went off in his hand and injured a noble lady in her arm. He fled and escaped, but gangrene claimed first the lady's arm and then her life, and he had to flee the region as her father put a huge price on his head. Later he tried to rob a priest with a pistol and sword, but the pistol discharged into the ground when he tried to draw it and the sword stuck in the scabbard, the priest being one who worshiped Mathom, the God of Delays
The only child of an earl, who was sent away for a planned arranged marriage, she was kidnapped by a highwayman who at first meant to get a heavy ransom for her. But somehow the two of them clicked and he and she quickly fell in love with each other. Within only a matter of months she was carrying out highway robberies with him. If she is caught soon and brought to trial and her father's lawyers cannot get her acquitted, she can at least plead her belly and thus escape the gallows and the gibbet, as she is now pregnant with the child of her highwayman lover.
The Robin Hood robs the rich (partly because the poor have very little worth stealing) and unusually genuinely does share some of his spoils of crime with the poor. Because of this he has a great deal of local support, and his supporters spy for him, refuse to betray him, and do what little they can to help him and give him succor in hard times. As a result it is very hard to track him down and either capture him or kill him. As long as he maintains the local support and refrains from doing anything stupid, he is almost uncatchable.
The Royalist was an army officer who thought for the King of his country against the King's Parliament. When the King lost the war, the King was brought to trial, found guilty and beheaded, whilst the officers of the royal army of major-general and above were locked up or forced into exile, and the royal army officers below that rank were dismissed without pensions for fighting on the wrong side. It was revenge for as he saw it being unfairly dismissed for fighting for the King that made him turn to highway robbery, targeting where possible the wealthy members of Parliament. In one case, he held up, robbed and very nearly shot dead the Parliament's Lord Chief Justice and made him beg on his knees for his life.
5-With this Kalashnikov in my hand
His country was occupied and he joined the resistance forces, and after a few attacks on military convoys he was one of those who survived long enough to be sent as part of a team to rob rich countrymen who were considered to be collaborators and use their money for the cause of his country's freedom. They wait until they leave their secure and guarded villas, stop them with a couple of stolen police cars and rob them or worse.6-The Lady
Frustrated that the frankly sexist laws and mores of her society have almost no legitimate roles for a middle class woman like her apart from wife or concubine, she has stolen a pair of pistols from her father, masked and disguised herself and become a knight of the road, delighting in particular in robbing the rich industrialists who she feels are responsible for restricting the roles of women, confining them to the most unpleasant jobs or preventing them from having jobs entirely.
The Novelist wanted to write a story about dashing highwaymen and decided that the best way to find out about them was to become one and carry out his own robberies. He had studied crime hard enough not to be caught, at least for the time being, and managed to write several best selling novels. If he had any sense he would give up his secret life of crime, but he finds it too enjoyable to give up.
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Update: (This was a 30 that was thought of years ago but I decided to free it from Mathom's grasp by making it into a 7 instead.)