STARRED REVIEW
June 30, 2020

How to write a bad boy (that readers can unreservedly love)

Behind the Book by
Joanna Shupe reveals how to write a hero who is the perfect amount of dangerous and lovable.
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Joanna Shupe’s latest historical romance series, Uptown Girls, follows three Gilded Age society girls as they find love outside the stifling ballrooms of high-class New York City society. In The Devil of Downtown, Shupe’s conclusion to the series, kindhearted activist Justine Greene falls for a man who would, by all accounts, appear to be her exact opposite: ruthless crime boss Jack Mulligan. But how can an author write such a character without making him too violent or amoral to be a believable love interest, nor defanging him so much that he loses the allure of the forbidden? In this essay, Shupe reveals her secrets.


Why do we love a bad boy?

It’s an age-old question, but one that perhaps a romance reader understands best of all. Many of us have loved stories with a charming rake or a ruthless billionaire.

But how bad is too bad? What about when the hero is a criminal?

All of the books in the Uptown Girls series have featured Gilded Age “bad boys”—men who make their own rules and profit handsomely for it. They each live by their own code of honor and can justify the reasons for their actions . . . both legal and illegal. The Rogue of Fifth Avenue’s Frank Tripp is a slick-talking lawyer who bends the law to fit his needs. Clayton Madden, the dark casino owner in The Prince of Broadway, is out to fleece every man in town with deep pockets.

In The Devil of Downtown, however, I went a step further. The hero, Jack Mulligan, is the criminal kingpin of Gilded Age New York City.

He’s a good guy, I swear. (But not too good. ☺)

“Good” vs. “Bad”
Part of what makes writing a criminal hero easier for me is the Gilded Age itself. Corruption was rampant in late 19th-century New York City. Many of the “good guys” were actually bad—such as the police, judges and politicians. And let’s not forget about the wealthy tycoons who underpaid their workers, used child labor and busted unions every chance they got. There were no rules, no laws, if you had enough money.

As long as you were rich, you could do pretty much whatever you wanted. So, the wealth of each Uptown Girls hero allows him enough power to create his own world, one where he makes the rules.

Using History
Historical research also helped when I was crafting each hero. Jack Mulligan is loosely based on a real-life Gilded Age figure, Paul Kelly. A boxer turned gangster, Kelly founded the Five Points Gang, which absorbed the smaller gangs of the area to become a large organization. He dressed like a dandy, spoke many languages and entertained members of high society at his clubs, and Kelly is widely considered the father of American organized crime. Lucky Luciano, Al Capone and Meyer Lansky are just a few of the men who gained experience within Kelly’s empire.

But there were parts I had to rethink for a modern audience. For example, while the real Paul Kelly owned brothels, this was a line my heroes would not cross. So I had to write in backstories for both Jack and Clayton Madden as to why they avoided the sex trade.

In Jack’s case, he was raised in a brothel and saw the violence sometimes inflicted upon women. It’s well known in his territory that he doesn’t tolerate the mistreatment of women, ever.

Show, Don’t Tell
I struggled with how to show the reader that a dangerous dude is really dangerous, even when he’s the hero. Because you can’t just tell the reader he’s bad, you have to prove it. Yet, the reader still has to like the character and root for him in the end.

It’s a delicate balance.

In fact, early beta readers of The Devil of Downtown told me the story needed more “devil,” that the hero was too nice. So I wrote some scenes where the violence either just occurred or was directed at someone he cared about.

Also, it helps to have another person who is even worse as a foil for the hero. Jack Mulligan has a rival trying to encroach on his territory. So most of Jack’s violence is directed at the book’s antagonist, a man who tries to kill Jack multiple times. In The Prince of Broadway, Clay’s ire is directed at the cops who try to swindle him and the men who try to cheat in his casino.

Gone, Baby Gone
All of the Uptown Girls heroes are head over heels for the heroines from practically the start of the book. This allows the reader to see a tender side, a squishy marshmallow center that contrasts his public badass persona. In a romance, this can help with likability because we need to believe that he’s lovable, that even someone who flirts with danger—or is knee-deep in danger—is worthy of a happily ever after.

He Did It His Way
We’ve all heard the phrase “honor among thieves.” The Uptown Girls heroes all have a very strong sense of what is honorable to them. Frank, the lawyer in The Rogue of Fifth Avenue, can justify anything that helps his client, even if it’s shady. Clayton Madden will never tell a lie, not for any reason.

And Jack Mulligan looks after the people in his neighborhood as if they were his family. Yes, he’s running the biggest criminal enterprise in the city, but he employs thousands. He punishes anyone who hurts women and children. He’s trying to make the Bowery and the Five Points a safer place for families.

So there are some tricks of the author trade that I used in The Devil of Downtown. Hopefully readers will find Jack Mulligan as compelling, sexy and dangerous as I envisioned him in my head.

Joanna Shupe

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