Another admitting of biases here, though in a somewhat opposite direction than before: I love rogue heroes. I like cheering for them. But I do think it’s too bad that the approach of many amateur authors to creating a rogue hero is to dumb down the legal system opposing him—or make it nearly nonexistent.
1) There is a large cache of stereotypes under the bed. Toss them out the window. These include: the dumb guard, the lecherous guard, the magistrate who takes endless bribes, and the sadistic captain. You can have people in the legal system who are dumb, lecherous, taking bribes, and sadists, but it’s far, far too easy to make these the only kind of people that your rogue hero encounters. So he gets to fool the guards by dressing up as a woman or performing other stupid tricks, he gets to feel triumphant that the magistrate who would judge him is corrupt, and he gets to kill the captain without a twinge of conscience.
Somewhere lost in the mess is the idea that the rogue has committed crimes, and is probably not entirely innocent of many of the same “sins” that the author condemns the legal stereotypes for holding. Also lost in the mess is the idea that such open corruption would get noticed and corrected, ruthlessly, even if the people who did the correcting weren’t very nice. Perhaps the people who replaced the dumb ones would be just as corrupt, but they would certainly be better at hiding it.
This goes back to the rant on secondary characters. Don’t make them stupid for the sake of making your hero shine. A nice twist might be the hero confidently dressing up as a woman to sneak past a guard he thinks is stupid, only to have the guard slam him in the groin with a pike and haul him off to jail, while explaining that two people have tried that in the last day.
2) Think out your trial system. Juries and judges are a fairly recent invention as far as real world justice systems go, along with the idea that a defendant is innocent until proven guilty, entitled to legal representation, and many, many others. Remember that the Miranda rights weren’t established beyond doubt in the United States until the 1960’s. It is unlikely that your fantasy world, unless it’s achieved a technological or magical level of living well above subsistence, would have the same concept of human rights as ours.
Too many amateur fantasies have juries and judges who are supposed to be impartial, even if they vary the number of jurors. Other times, they have heroes who are outraged that such things don’t exist—for example, that the judge is not impartial—even when the systems of their worlds are very clearly set up differently.
Unless there’s a good reason for it, like your hero coming from the modern world, don’t affix modern feelings and customs to your fantasy world’s legal system. The medieval world included many customs we would find unfair, such as trial by ordeal, but if “unfair” suits your fantasy world better, then adopt it, or come up with something in keeping with your world. Don’t slap modern legal ideas down in a world where they’ll stand out like a second nose, just because you don’t want to shock your readers’ delicate sensibilities.
3) Cells should not be easy to escape from. It seems that no matter how well guards make their cells, those dratted rogue heroes keep getting out of them.
It shouldn’t be that easy. Consider: The stereotypical fantasy cell is stone on three sides, with iron bars along the fourth. It’s covered with foul-smelling straw. It has a chamber pot and possibly a cot. It has rats. It most likely has spiders. The guards leave food and water once a day or more often. The prisoner doesn’t have any keys.
Yet people manage to stroll out of them all the time.
Most of the ploys they use are transparent, and dependent on the stupidity of the guards. They’ll pretend that someone in the cell is sick, for example, and get the guards to come in alone. They’ll wait until food and water are delivered, and attack then. They’ll throw the chamber pot and escape while the guards are choking on the mess. In the most extreme cases, they somehow manage to hack their way out through solid stone or open the locks with weapons or lockpicks the guards somehow missed.
In anything resembling reality, it’s unlikely these would work. The guards should know better than to send someone in alone, or come alone when they bring the food. The chamber pot probably won’t be available as a weapon, and even if it was, there’s no guarantee that a blinded guard striking at a prisoner would miss every single time. And experienced guards would have no reason not to strip a prisoner naked and search him or her carefully for weapons.
Don’t make the cells a snap to get out of, particularly if your heroes are wounded. Assume the guards have at least a modicum of intelligence, that use of these cells would have been discontinued if people could escape so easily, and work from there.
4) Consider how people in the legal system will see your heroes. If your hero is a rogue and has stolen a great amount of things, the guard captains and judges are unlikely to share in his self-congratulations. Put yourself in their shoes and think for a moment. How would you react if your house was burglarized, or if you were responsible for protecting houses that were being burglarized? Anger and helplessness are understandable reactions, not stupid ones, as is the desire to resist celebrating the rogue as a hero.
If your heroes aren’t rogues, just wandering adventurers, also try to think how a guard captain would react to these dangerous, careless, irresponsible people walking through a town it’s his duty to protect. The heroes might be able to sneer at dead enemies and fires in houses, but then, they don’t live in those towns and don’t feel as if they were at home there. It’s quite different for the people who lose loved ones and homes, or at least have to clean up the bloodshed and arson, and it would be careless to demonize them for those reactions.
5) The heroes shouldn’t be the only ones with unusual skills. Guards in fantasy seem to consist almost exclusively of armor-wearing, hard-drinking men who aren’t very skilled with their swords. If their weapons aren’t swords, they’re pikes or spears, and they don’t know how to use those. Yet somehow they’ve managed to effectively oppose everyone until the heroes come along.
Why not let there be archer guards occasionally? Or good swordsmen? Or former thieves who could follow the heroes around on rooftops and evade their booby traps? Mage guards would be interesting. So would women, or guards of other races, like elves, who would have skills that the heroes are used to possessing only for themselves. All of these would have some claim to effectiveness, and would give the heroes a challenge, in the same way intelligent prison guards would.
And look at it like this: Your heroes would have to work twice as hard to defeat them. If they outshone them anyway, they would look far better than if they just conquered the usual guys who rush in to be hacked to death like idiots.
6) Guard captains and judges are likely to have resources. At the very least, they’re going to have better connections in their hometowns than wandering heroes. That means they could probably pay someone to keep an eye on the heroes, or pick up reports of unusual strangers from townspeople they already know. They may even have a full-fledged spy network. It boggles the imagination when a hero who has never been in a town before can walk in and vanish from the eyes of a captain who’s been commanding the same guards in the same town for twenty years.
Guard captains and judges are also likely to know the town itself better. They’ll know the best hiding places, the people rogue heroes might turn to for help, the notorious thieves. They won’t wait to look for a thief just to nicely make it convenient for him to rob a house.
7) All those feisty heroes should get slapped down at least some of the time. This is another very common device: to have a witty rogue hero whose every word makes the guards gape in silence, or look foolish if they try to respond. If that really has to happen in your story for plot reasons, guards trained to violence are likely to resort to violence at the very least. That feisty rogue hero can probably count on at least a few bruises, and bad treatment in the cells, like late food or drink the guards have pissed in.
It might be even more interesting to have a witty guard who can answer back, or someone, probably the captain, who’s seen this all before. For a good example of this (and many other ways of breaking the stereotypes about guards), read Terry Pratchett’s City Watch subseries. That tells the story from the viewpoint of the guards, especially their commander, Samuel Vimes, and the criminals convinced of their own brilliance can seem just as foolish from the opposite side.
Other than parents, guards seem to be the demonization target of choice in fantasy. I don’t really know why, considering how great a problem thievery and violence are in our world. Maybe it’s just easier to cheer a rogue hero from the armchair than to think about what it would mean to face one.