Tag Archives: writing thieves

Any advice on how to write a heist story something like oceans Eleven?

Well, you can start by watching Ocean’s Eleven, and Ocean’s Eleven, and then Leverage, and then Burn Notice, and then The A-Team, and then Mission: Impossible, and then all the other heist stories like The Italian Job or Heat. Watch, read, uncover as many stories about criminals as you can from fiction to nonfiction to reading security analyst blogs. Read the spy memoirs, the thief memoirs, the fake ones and the real ones. Check out magicians, hypnotists, card tricks, and sleight of hand. Watch the making ofs and director’s commentaries looking for clues behind the thought process of these stories. The hows and the whys as you look into the research they did. Burn Notice, for example, is famous for using stunt props and technological rigs that work in real life. Like using cell phones to create cheap bugs on the go.

The worlds of criminal fiction and spy fiction rely on being able to present (or convincingly fake) a world which feels real. A heist is all about exploitation. So, you need a world with security structures to exploit. You’ve got to know how things work before you can craft a way to break them. Social engineering, hacking, and every other criminal skill is about breaking the systems in place. So, you’ve got to get a baseline for how law enforcement and security analysts work. What security systems are set up to look like. The ways we go about discouraging thieves. Better yet how people behave. Real, honest to god human behavior.

So, you know, pick somewhere in order to start your research. Get an idea of what you want write about stealing, then learn everything about the object, the museum, the city, the country, and its customs as you can.

If you’re setting a heist in a futuristic or fantasy setting then luck you, you get to make all of it up.

Learning the plot structure and conventions of the heist genre is the first step. This means watching lots and lots of heist movies, shows, and reading books. Over time, as you become better at critical analysis, you’ll begin to see specific story structures and character archetypes emerge.

The Heist Story is a genre. Like every other genre, it comes with its own structure, cliches, archetypes, plots, and genre conventions which necessitate the narrative. The better grasp you have of those, the better you’ll be at writing a heist.

For example, a heist story like Ocean’s Eleven relies on a collection of thieves rather than a single individual. The character types are as follows:

The Pointman – Your planner, strategist, team leader, and the Jack of All Trades. Can also be called the Mastermind. They’re the one who can take the place of anyone on the team should they fall through. They’re not as good as a specialist, but they’re very flexible. Narratively, he plans the cons and subs in where he’s needed.

The Faceman – Your experienced Grifter, here for all your social engineering needs. These guys talk their way in.

The InfiltratorYour cat burglar or break-in artist. Basically, the conventional genre thief. Your Parker, Catwoman, Sam Fisher, or Solid Snake. The stealth bastards, they’re all about silent in, out, and playing acrobatic games with the lasers.

The Hacker – The electronics and demolitions specialist. Usually this is the guy in the van overseeing stuff remotely. Your Eye in the Sky. Their skill set can be split up and swapped around as necessary.

The Muscle – The one who is good at fighting. They’re combat focused characters, usually with mercenary and special forces backgrounds. Though, that’s optional.

The Wheelman – The one who handles the getaway. They’re your often overlooked transport specialists. It’s not just that they can drive, they’re skilled at getting lots of people around, figuring out how to move your valuables, and exiting hostile cities or countries undetected. They get the team in and they get them out.

For an example of these archetypes, I’m going to use Leverage. Nathan Ford, The Pointman (technically, he’s written like a Faceman). Sophie Devereaux , The Faceman. Parker, the Infiltrator. Hardison, the Hacker. Eliot, the Muscle. They all take turns being the Wheelman.

Other examples like Burn Notice: Michael Westen, the Pointman. Sam Axe, the Faceman. Fiona, the Muscle. They all take turns with explosives, Michael will invariably take all the roles during the course of the show.

Ocean’s Eleven has multiple variants of these archetypes, all broken down and mixed up.

You can mix and match these qualities into different individuals or break them apart like in Ocean’s Eleven, and more than one character can fill more than one role, but that’s the basic breakdown. For example, your hacker doesn’t need to be a guy in a van overlooking the whole security grid. One guy or girl with a cell phone can sit in the lobby of a building with an unsecured wireless network and crack the security. Welcome to the 21st century. The skills don’t necessarily need to take the specific expected shape.

What you do need is the basic breakdown:  You need someone to plan the con, you need someone to be your face or grifter, you need someone to break in, you need someone to watch the security/electronics, you need muscle to back you up, and someone’s got to cover the getaway.

These shift depending on your plan, but this is the expected lineup for a heist narrative. The first step of a heist narrative is not the plan because we don’t have one yet. We’ve got an idea. Pick your target. Maybe it’s a famous painting. Maybe it’s a casino. Maybe it’s a rare artifact from a private investor’s collection loaned to a museum for a short period of time. Maybe it’s art stolen by the Nazis during WWII. Whatever it is, figure it out.

The next step is simple. If you want the thing, you’ve got to find a way to get it. This is a big job, your standard thief won’t be able to pull it off alone. So, you gotta go recruiting. Get your team together. Make sure to establish the goals of the different members for joining. Who they are. Their pedigree. One might be an old flame or an old enemy. This is where we lay out some character driven subplots.

When everyone’s together, we’ve got to lay out the plan. Before we have a plan though, we need to establish where the object is and the issues in getting it. Why this has never been done before. So, what are the challenges? Invariably, an object worth a great deal of money will have a lot of security protecting it. Figure out what that security is, who the item belongs to, what sort of retribution do the thieves face beyond what they might expect. Lasers, pressure plates, cameras, security, other career criminals, mob bosses, the rich and powerful, whatever.

After that: How do you get it? Then you’ve got to plan the con, while taking everything into account.

Then, We prep the Con. There will be steps to take before the con can be put into place, your characters taking their positions in plain sight. Stealing whatever pieces you need to make it work. Casing the joint. Etc.

Then: Run the Con. This is the part with the actual stealing. Better known as the first attempt. Things go well, there may be a few mistakes, but things are going well and then we…

Encounter Resistance. While running the con, something goes wrong, pieces fall apart, the thieves come close to success but the object gets moved and they suddenly need a new plan. New information may pop up, it may be one of your artists was running a con of their own separate from the rest.
If there’s a double cross in the works then this may be when and where it lands.

We’re ready now, so it’s time hit up: Steal the Thing, Round Two. Your characters put their new plan into play and get about thieving the object of their desire.

Lastly: The Get Away. This is the part where your thieves make for the hills with their stolen treasure. This can be short or long depending on the kind of story you’re telling and other double crosses may occur here. It could be the end of the story or the beginning of a new heist.

Heist stories are like mystery novels. They’re all about sleight of hand and misdirection. You’ve got to keep just enough information on the table to keep your audience on the hook, and just enough information off the table to surprise them later on the twist. Yet, when they go back to re-read the novel again, they’ll find the answer was there all along. They just didn’t see it coming.

If anything, learning how to write a well-done heist or a mystery or any kind of novel in this genre will teach you a lot about how to manage your foreshadowing and create superb plot twists. Like any good con, you need to lay out all the conflicting pieces where people can see them, let them draw their own conclusions, withhold the critical context, and then hit them with the whammy.

Like lots of audiences, new writers (and even some old ones) can get distracted by the shock and awe. They see they’re impressed by the conclusion, not the lay-up. If you want to write any kind of fiction, you need to learn to see past the curtain and pay attention to the critical pieces leading into an important moment rather than the moment itself.

Good writing isn’t modular, you can’t just strip out pieces and run with them because you’ll end up missing the crucial, sometimes innocuous pieces that ensured the scene worked. Like the Victorian Hand Touch, every moment between the two leads and most of their scenes with secondary players are working for that singular instance of eventual, gleeful catharsis.

If you’ve got a plot twist coming in your novel, every sentence from the second you start writing is working towards it. You start laying out your pieces, funneling in your tricks, and playing with misdirection. You may have multiple twists, to cover yourself, divert your audience, congratulate them for successfully guessing your ploy, and reassure their initial suspicions before catching them again on the upswing.

The clever writer is as much a con artist as their characters. The only difference is the target of their con is their audience. The tricks in their bag are narrative ones, and they work with the understanding that it doesn’t matter if someone guesses the end so long as they’re entertained by the journey. A great story stays entertaining long after the audience has figured out all the twists.

So, don’t get caught up in Red Herrings and frightened about not being able to outsmart other people. Tell a good story with conviction and heart about a bunch of crooks out to steal their heart’s desire.

That’s all there is to it.

-Michi

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Hi there! I love your blog! I’ve seen you mention a few TV shows and movies for research, and I was wondering what your opinion is on the show Leverage and it’s accuracy for social engineering in potentially violent situations. I remember one character saying that “Thieves look for entrances, but grifters create them.” They’ll often use approaches like this to avoid violence.

If the question is: can you use social engineering in order to defuse or avoid violent situations? The answer is yes.

Grifters are conmen, and like spies, they don’t want to fight unless it is absolutely necessary. Whether they can fight or know how isn’t really the point: combat makes messes, big messes, and draws the kind of attention they don’t want/can’t afford.

As for the line, “thieves look for entrances, but grifters create them” the point of it is that grifters focus on people as the exploitative aspect to get what they want. After all, it doesn’t matter how good your security system is if your infiltrator is expected to be there. When someone opens the door for them, they didn’t have to break in.

It is worth pointing out though, being able to stop, defuse, avoid, or redirect violence via social engineering (especially when the character is the target) is very difficult and requires someone who excels at rapidly changing their story/manipulating under life or death pressure while also maintaining their consistency/re-establishing their innocence/regaining their target’s trust.

That’s masterclass social engineering. The average person, even the average grifter can’t do it. When we see Nate Ford, Sophie Devereaux, or Michael Westen on Burn Notice socially engineer their way out of potentially explosive and violent scenarios, we’re supposed to understand this level of manipulation is very difficult. You need a solid ability to read people, predict their behavior patterns, understand how to shift your role so you suddenly seem trustworthy, confuse them, and then redirect their anger somewhere away from you.

You can see another variant of this kind of social engineering on display in The Negotiator. Samuel L. Jackson’s character is a hostage negotiator. Deliberately maneuvering a man who’s taken a child captive around his apartment so he can be taken out. You can see him joking with the target, gaining his trust, distracting him, and guiding him off topic until he’s in a position to be neutralized.

The Grifter is not a fighter, they are a talker and their trick is getting people to move however they want. A skilled grifter can slip in, turn the best of friends against each other, and walk away without a care. Grifters don’t punch. They trick other people into doing the punching for them. When sitting down to write a Grifter, remember: their first instinct is getting others to act in their place, to create the openings they need, and be their fall guy.

On the whole, I’ve liked Leverage ever since the episode where Eliot pointed out that guns are ranged weapons, and the most common mistake people make is giving up the distance advantage by getting in too close. However, I’ve only watched the first season. I liked what I saw, it’s an enjoyable caper show in a similar vein to The Equalizer, Person of Interest, or Ocean’s Eleven. Not quite in there with the original Law & Order when it comes to accuracy (in this case for cops) but certainly better than White Collar, which uses similar techniques (though never, ever pay attention to White Collar’s usage of the FBI… ever). The X-Files, meanwhile, fudges a bit but it’s pretty good when you’re wanting to get a grasp of the FBI’s culture and what happens to someone who doesn’t come from a military/law enforcement background.

Of course, the patient zero for these types of shows is the original Mission: Impossible. The television show, not the Tom Cruise movies. Mission: Impossible is all about flipping people and manipulating them into positions to do what you want. The A-Team is its slightly more pulpy counterpart, but its a similar (though far less subtle) deal.

On the whole, Leverage tends to explain itself better, which is helpful when you’re trying to learn or take techniques from a television show rather than just absorb.

The reason why I often suggest Burn Notice and Spy Game is not necessarily just because they’re good, but also because they teach. The narrator on Burn Notice, especially in the first season will offer up a lot of helpful/beginner tradecraft for a variety of situations. This, ultimately, will help you more for taking pieces and creating your own characters than a show that’s trying for smoke and mirrors like White Collar. The same situation is there with Spy Game, where Robert Redford’s character is teaching Brad Pitt’s on how to be a spy. Ultimately, more helpful in the long run than just watching The Recruit. The Michael Mann films like Heat and Collateral are exceptionally good for learning tradecraft, but you have to know that’s what you’re watching/looking for. You’ll learn more by watching them together, rather than separately. The Borne Identity novels are also very good at showing the tradecraft, while the Le Carre ones tend to be a little more hit and miss.

When you’re new, you want sources that are free with their information. Who are good at getting you to think, to take what you’re seeing and apply it to new settings. You may not ever figure out how to build a car bomb, but learning about how the thought process of a spy, criminal, or conman works will serve you better for your writing than a hundred other movies that only show.

After you’ve drawn back the curtain then you can turn to those other shows, novels, and narratives with new eyes. Once you see what they’re doing, how they’re doing it, and why when they don’t explain you’ll get more out of those other sources than you did before.

When you’re watching a well put together show like Leverage, start questioning character motivations. Not just whether the social engineering there works, but why the characters are choosing to go that route or which routes they prefer. Leverage gives you five characters with different specialties, four thieves and the guy who made a career catching them. They all think in different ways and have different approaches when it comes to problem solving. Leverage offers up a heist per episode, so you have lots of opportunities to see the characters in action. Evaluate their problem solving methods and you’ll come away with more than just questioning whether or not it works.

How and Why.

Then, go find a good video on YouTube where a professional magician explains pickpocketing. It’s the art of misdirection.

Once you understand basic theoretical underpinnings (whether or not you could ever actually pull the real thing off) then you can apply it to many different situations in a fictional context.

When it comes back to applying this to the combat arts, learning to see the big picture is the first major difference between trained and untrained. The untrained only copy surface level, singular techniques, while trained delves deeper to understand how these techniques work together.

My advice for when you’re wanting to pick and choose television shows for accuracy is to check who their consultants are/were, and what experts in the show’s chosen field say about it. That doesn’t always guarantee accuracy, but it will help you flip through the rave reviews.

If you want to watch more fun shows with Timothy Hutton or just like detective shows, I recommend Nero Wolfe.

-Michi

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I have a character who is a thief, and for squeezing-in reasons she can’t have anything but leather armor. So, what weapon would she carry around in case she gets caught by any full-armor-wearing enemy? I was thinking a Misericord? Thank you!!! *hug*

I feel like we’ve covered this before. A dagger isn’t going
to do much when you’re fighting against an armed and armored guard. For that
matter, neither is the leather.

If your character’s going to be going up against guards who are
armed with sidearms (maces, swords, whatever), going after them with a dagger
in a straight up fight is suicide. A knife fighter needs to get much closer to
the target than a swordsman. This means they need to get past the sword. Against
any competent, or even semi-competent combatant, trying to rush past the sword
will end with your character impaled.

The obvious solution to carry a sword of your own, isn’t
necessarily an option either, because 99% of the time, it’s just going to get
in your character’s way. It will hit things, get snagged, make noise, and this
will draw the attention of those same guards your character is trying to avoid.

If they wanted to make good on killing people with the
dagger, then their best bet would be coming in from behind, when the guard
doesn’t see them, and slitting their throat. However, this will cause other
problems.

Your character is a thief, they’re already a part of the
underworld that can easily draw the ire of the people who run their world simply by stealing something too prominent or important. This is a
classic genre hook for a reason.

If you have a thief slipping off with a few gems or baubles
and getting out undetected, that’s just a thing that happens. It could have
been the servants, it could have been a mistake, or it could be any number of
other possible scenarios.

However, if you have a thief slipping into homes and killing
people, that will make the setting’s elites feel unsafe, which will lead to
them pushing the city guard to crack down on the underworld. At that point,
your character will put her allies in danger. Remember that old cliche? “No honor
among thieves.” When the city guard is kicking down doors, and kneecapping
fences, it’s not going to take long for someone to offer up your character’s
name, if only because they hope it will let them walk out of their cell with
one or two functioning limbs.

It’s worth remembering, if anyone in the setting’s underworld, knows she’s the one who started
this, they will hold her directly responsible for bringing the guard knocking
through their door, and ruining their livelihood.

As I mentioned earlier, a classic genre hook is a thief
accidentally stealing something ridiculously valuable. It may be an ornate
artifact with ties to some eldritch power, it may be documents that implicate
their victim in some conspiracy, it may simply be a piece of absurdly valuable
jewelry. In any of those cases, it can result in a similar crackdown, no dead
bodies necessary.

Any competent thief is going to know they should avoid
drawing too much attention to themselves. They can still get into messes like
this unintentionally, but if a guard spots them, it is far safer for them to run, and escape, rather than stand and fight.

If your character was an assassin, then, yes. I’d say taking
a few daggers, a garrote, and maybe a few other fun little party favors is a
good idea. The basic thought with fighting guards would be the same, take them
out without giving them any opportunity to fight back, or avoid them entirely.
That said, assassins are an entirely different animal, they don’t rely on persistent
contact with the setting’s underworld the same way thieves do. They just need
to get paid, they don’t need to fence what they’ve stolen, or keep appraised of
what the City Watch is doing, or stay coordinated enough to avoid tripping over
each other on jobs. An assassin just needs a client (who isn’t necessarily part
of the underworld) and tools (which they may be buying through legitimate
channels and modifying on their own). They may still bring heat down on the
underworld, and make life miserable for the city’s thieves, but they’re much more insulated from that world than your character would be.

I mentioned earlier that leather armor might not be a good
choice for your character. It won’t do much to protect your character from a
guard, but that’s not the real problem. The big issue is that it will announce
that your character isn’t just part of the background. Under the best
circumstances, a thief needs to be able to blend into the crowd and disappear.
If they’ve got a cloak, a dagger hidden away, and a few deep pockets, that’s
going to be much harder to spot in a crowd than someone wearing armor.

Beyond that, if your character is climbing or squeezing into
places, the leather will just be more weight to move around, and more bulk to
pull through tight spaces. Granted, it’s not a lot of weight or bulk, but if
her goal is to remain undetected, then it’s not doing her any favors.

Carrying a dagger is a good idea, but not to use as a weapon.
Knives are very useful utility items, and that’s no different for your
character. It can be used as a
weapon, but it’s something your character would probably want to avoid unless
they were desperate.

So, stab them in the neck and run like hell, I guess. Or, you
know, don’t bring a knife to a swordfight.

-Starke

On the subject of writing about thieves, or a criminal underworld, in a fantasy setting, the first thing that comes to mind are the Fafhrd and Gray Mouser stories by Fritz Leiber. If you’ve never heard those names before, they’re really worth taking a look at.

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I am writing a chase scene for a fantasy thief story. Reminiscent of the Thief games. Any advice?

Remember that Garrett isn’t a fighter. The games have been a little inconsistent on this point, but the character your looking at is one who survives on staying out of sight, avoiding detection, and only removing guards when there is no other possible option. In a straight up fight, he will lose. It’s just not his skill set.

Ironically, if you’ve been playing the games, you should have a pretty good idea how to follow his approach to hostile environments. As with everything else, it varies between the games, but Garrett’s best approach to danger is slipping away undetected.

If he’s being chased, his best option is to find a way to disappear. Although it’s not a very Thief concept, blending into a crowd and slipping away is one of the best immediate responses. Failing that, finding ways to take a path his pursuers don’t see, or can’t take is the other solution. Garrett caries a lot of specialized tools, including things like the flash mine to deal with pursuers. Whether he uses the resulting confusing to blackjack everyone who was stunned, or escapes is up to you. These kinds of gadgets are, somewhat, a staple of this archetype, so it’s not an unreasonable suggestion.

-Starke

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