A Criminal Hero and the Caper That Almost Wasn’t

One of the truths about crime fiction is that no one’s hands are clean. For me, that’s often the point. Most of my stories involve protagonists who are generally good but find themselves in situations that force them to bad things for the right reasons. In The BadShepherdwe see Bo Fochs working outside the system when he believes that justice won’t be served unless he does. Then we see him face the consequences of those actions. Put simply, he does bad things for the right reasons because he believes no one else will.

For my next book, though, I wanted to explore a protagonist on the other side of the law. In A Legitimate Businessman, due out later this month, our hero is a professional thief named “Gentleman” Jack Burdette. This was a lot harder than I thought it would be. When I set out to write the book, really what I wanted was an Elmore Leonard-style caper story with colorful characters, snappy dialogue and a casual attitude towards the law. However, I quickly found that in writing it, I couldn’t connect with my character because he was a criminal. I couldn’t justify the things he did enough to care about him. He stole things, it was exciting to write but I didn’t care. It was hard for me to empathize with a crook. I worried that my readers would too.

When I finished the first draft of this book, I’ll be honest, I didn’t like it. I didn’t know what I had. I also didn’t like my hero. Oh, I thought he was written well and everything he did was true to his character…but I didn’t like him. I didn’t care whether he survived the book or not. As protagonists, criminals are a different breed than anti-heroes and are harder to draw out because they are fundamentally “bad”. Because of that, I think, they are much harder to get right.

Without giving anything away, part of how I squared this particular circle was to make Jack the least of the criminal characters in the book. By comparison, he’s not such a bad guy. I also gave him some legitimate motivations. Even if you don’t agree the choices he makes, you can see why he does it and it fits within the world of the story. Through the editing process, I was able to shape this character, find his true self. I was able to give him a kind of code and a reason for being that not only made him fun to write but also fun to read.

I love “Gentleman” Jack and he’s one of my favorite creations. I also think this book is some of my best work and I cannot wait to write more books with him. That’s a long way from staring at my first draft and wondering if I was ever going to release it. The wonderful lesson in this, both for writers and readers, is that to get truly invested in a book and a character, we need to have enough of a connection with them that we feel genuine empathy for them so that we understand the choices they make.

Richard Stark’s Parker is a purely amoral criminal who steals without compunction. By comparison, Elmore Leonard’s Chili Palmer is a mobbed up shylock who is trying to go straight (-ish). With the former, we don’t care about his motivation–we also aren’t given any, which is part of the beauty–we only read the book for the caper. With the latter, Chili is trying to go straight by moving from one very criminal enterprise (loan sharking) to a slightly less criminal one (Hollywood). With A Legitimate Businessman, I was trying to thread the needle between these two, create a criminal protagonist who does criminal things, makes no apologies for that but is also one we genuinely want to see get away with it.

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