Gentlemen and Scoundrels: Writing A Sympathetic Thief

A while ago, I brought a short story to a writer’s workshop. It was the story of a thief-for-hire trying to get his hands on some blueprints, only to stumble across a heavily secured lab.

            One of my readers told me that he didn’t like my main character, mostly on the grounds of him being a thief.

            But there are plenty of likeable thief characters in fiction. So, how do you separate the villainous thieves from the merely neutral ones?

            Backstory—Every character has a backstory. Why is your character a thief? A sympathetic thief will have his roots based in poverty, where stealing is the only way he can survive. Perhaps he was orphaned, perhaps his family is just too poor to afford even the most basic of needs.

            A villainous thief is someone who doesn’t need to steal to survive, but does so anyway.

            Motivation—Why does your character steal? A good thief steals because she needs money for necessities: food, clothing, rent. A good thief steals because his mother/wife/child/ whoever is sick, and an honest trade will not cover the medical expenses. A good thief may no longer be in the poor house if he’s older and very good at his job, but he might continue to steal because it’s the only way he knows how to make a living.

            A villainous thief steals for cheap thrills or out of a sense of entitlement or greed.

            Where’s the loot go?—Depending on your thief’s circumstances, the money/loot will go to different places. Some use it merely to make sure they can keep a roof over their heads and food in their bellies. Sometimes they gotta pay off a big debt. Maybe they’re not stealing for themselves, but for the people around them without the skills to do so for themselves.

            Or are they hoarding the loot for themselves? Or maybe using it to fund illegal and unsavory activities? Perhaps they don’t do anything with the loot, only taking it so that someone else couldn’t have it.

            What’s their moral code?—Most sympathetic thieves will not steal from people who can’t afford the loss, preferring somewhat wealthier targets. They almost always go out of their way not to kill, even in self-defence. There may be other morals, but these two are the big ones that will separate a good thief from a bad thief.

            As a rule, thieves are usually a neutral fraction in anything. Very rarely do they involve themselves in the overall conflict going around them. Thieves who don’t eventually end up involved in the climax rarely serve as protagonists. A thief character with a strong moral code will join in the conflict because she doesn’t want to see innocent people hurt, despite her criminal past. In another case, a thief character will do his best to actively avoid getting involved in the conflict until he’s into deep to back out, or the conflict becomes personal.

            Of course, thief characters can have a wide variety of personalities that can either add to or take from their likeability. It’s all about how you mesh these abilities together. Here are some sympathetic examples that I’ve had experiences with.

Robin Hood—Let’s start with a classic good-guy thief. Charming, debonair, witty. Robin Hood actively involved himself in the conflict of his story, stealing from the rich to give to the poor. We like this type of guy because he’s against corruption and always looks out for others. If your thief character is anything like Robin Hood, chances are we’ll be rooting for him.

Sly Cooper (from the Sly Cooper games)—Now, Sly was born into thievery (though he was orphaned at a young age) and genuinely enjoys his work, partly for the infamy, and partly for the thrills. There’s a good hint that he could get out of thieving and become a law-abiding citizen, but he chooses not to. However, Sly’s got a strong moral code. He won’t stand to see innocent people hurt and he’s always actively involved in stopping the villain. It also helps that he comes from a line of thieves that specialize in stealing from other thieves (mostly).

Garret (from Thief)—The 2014 reboot of the series sums up Garret rather nicely: “At first, I stole to survive. Now, I survive to steal. It’s all I know and all I will ever know.” Garret falls under the “orphan who had to steal to survive” section of backstories (which brings him into the Keepers in the original trilogy, a segment of his backstory absent from the latest game). Garret’s probably on the less likeable spectrum because he truly enjoys what he does, and hires himself out. What makes him likeable is his dry wit, love of awful puns, refusal to kill unless he has no choice, and how we can always trust him to save the City for one reason or another.

Locke Lamora & Jean Tannen (from Scott Lynch’s Gentlemen Bastards Sequence)—Though their methods are more akin to those of con-men, Locke and Jean both consider themselves thieves to the bone. Both are orphaned, both were raised by a former master thief, and both have excellent skills in both the conning side and the traditional B&E side of thievery. Unlike the previous examples, they have no issues torturing or killing the people who make enemies of them. However, they’re charming and witty, have genuinely strong feelings of loyalty and kinship to their friends, primarily steal from the large corrupt aristocracy, and have actively risked their lives to save people to whom they literally owe nothing out of a sense of moral obligation.

            And those are my tips for separating the sympathetic thieves from the scumbags. Please note that this post refers to fictional thieves.

            Stealing is wrong and you shouldn’t do it.  

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