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Bootlegger’s Apprentice follows a young bootlegger through the violence and glamour of Prohibition-era Chicago as he discovers that escaping the criminal underworld may be the only way to protect his family. What was the inspiration for the setup of your story?
I fostered an interest in Irish American organized crime from on-screen stories such as The Departed and Boardwalk Empire, through histories of Prohibition Chicago, and fiction such as Don Winslow’s City on Fire trilogy and Mary Miley’s Spirits and Smoke. My family is heavily influenced by my Irish American Grandma Margaret Miller (nee McCarthy), and I combined that with my own experience growing up Catholic (I am now Agnostic) surrounded by strong women to create Aiden McCarthy.
How did you balance real figures and events with Aiden’s fictional journey?
Figures like Louis Armstrong and Mezz Mezzrow, along with real clubs, allow me to really explore Aiden’s interaction with the jazz scene, intoxication, and the experience of African Americans. Much like my own growth from a predominantly white childhood to encountering folks of all different skin colors, Aiden finds beauty in those with different backgrounds. I wrote Aiden’s story to respect and be real about history and race. His friendship with William Crutchfield, Dean O’Banion’s actual porter, is written as a nod to my own experience. I aim to give the story more flavor.
Aiden grows from being bootlegging muscle to club negotiator to having to kill in self-defense. I textured his moral journey with actual events in Dean O’Banion’s history where O’Banion’s hubris eventually gets the best of him. Aiden comes to terms with life-and-death decisions as O’Banion makes a fatal mistake.
The novel writes O’Banion with a certain degree of charity, but he really was rather open-minded for his day on African Americans and homosexuals. “They can’t help how they are” is a direct quote from an O’Banion biography.
Al Capone, Johnny Torrio, and various politicians and police who encounter Aiden and O’Banion allow me to inject a certain amount of authenticity into how I imagine Jazz Age Chicago. I enjoy figures such as crusading journalist Robert St. John, who formed an uneasy defiance to Capone and is interesting to me because of my background in journalism. The corruption really existed as portrayed, but I did take quite a bit of liberty to make one of O’Banion’s antagonists into a juicy character.
The novel handles Al Capone as a human who cares for his family, his partially deaf son, and his older brother mainly. He is also a thug driven by an inability to cope with sorrow (no spoilers) and his place in the mob hierarchy.
At what point in developing the novel did you know that Aiden would spare Capone and bargain for his family’s safety instead?
Al Capone has to live, but I want Aiden to really challenge his morality when it comes to using lethal force. Aiden has a certain ethical code, sees the logic in his decisions, and is supported by strong women to make better choices. I don’t want to give away any spoilers.
What is the next book that you are working on, and when will it be available?
I have started a prequel to my Ron & Carey series. The series is about an Army veteran, Ron McCallister, who charms adversaries and his lover alike while outmaneuvering crooked politicians and bloodthirsty thugs from 2008 to 2009. I want to explore Ron’s return from Iraq around 2005 and run-ins with the Chicago Outlaw Motorcycle Club and corrupt authorities as he reconciles his new reality and eventual introduction to a stripper with a heart of gold. While Ron broods and kicks ass, his Aunt Peggy serves up homespun spitfire, much like my Grandma Margaret and Great Aunt Ethel.
I’ll maybe publish it in about five or so years. Good stories take time!
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Chicago, 1924. Prohibition has made criminals rich, politicians dangerous, and loyalty a currency all its own.
Aiden McCarthy is a young Irish American drawn toward a life far more dangerous than arranging bouquets.
Working under notorious gangster and florist Dean O’Banion, Aiden is drawn deeper into a world where bootleg whiskey, political corruption, and organized crime collide, and where men like Johnny Torrio and Al Capone are reshaping Chicago from the shadows.
Yet amid the violence and intrigue, Aiden has something worth protecting. His relationship with Sophia Golino offers the promise of a life separate from the dangerous men who increasingly depend upon him.
Around them, the clubs and speakeasies of Jazz Age Chicago pulse with music, temptation, and shifting social boundaries.
As rival gangs maneuver for power and a bitter political struggle threatens to turn deadly, Aiden must learn quickly whom to trust, when to fight, and just how much of himself he is willing to sacrifice to survive.
A richly imagined historical crime novel of gangsters, romance, jazz, family, faith, and ambition, set against one of Chicago’s most notorious eras.
Step into Prohibition-era Chicago, where love, loyalty, and one wrong choice can cost everything.
Bootlegger’s Apprentice
Ben Broeren’s Bootlegger’s Apprentice drops the reader into Chicago during Prohibition and follows twenty-one-year-old Aiden McCarthy as he moves deeper into the world of bootlegging under North Side Gang boss Dean O’Banion. Aiden starts out with the confidence of a young man who thinks he understands the game, selling liquor, arranging flowers at Schofield’s, and enjoying the access his work gives him to speakeasies and jazz clubs. That confidence gets tested quickly. Hijackings, political intimidation, crooked law enforcement, and the growing hostility between O’Banion and Al Capone turn what feels like an exciting racket into something much more dangerous. Broeren makes good use of actual people and events from 1920s Chicago, weaving figures such as Capone, Johnny Torrio, Louis Armstrong, and O’Banion into Aiden’s fictional story without losing sight of Aiden as the book’s emotional center.
One of the book’s strongest qualities is the way it treats organized crime as part of a much larger city. Bootlegging overlaps with politics, race, religion, music, family life, labor, and ordinary business. Aiden’s visits to the Sunset Cafe in Bronzeville, his involvement in Cicero’s violent election, and O’Banion’s combination of flower sales and criminal negotiations all give the novel a Chicago that feels busy and interconnected. The historical details are everywhere, from streetcars and newspapers to slang, food, firearms, music, and neighborhood tensions. Broeren’s prose has an energetic, descriptive style that often mirrors Aiden himself. It likes a joke, a colorful comparison, and a period expression. That gives the book personality, while the frequent shifts to O’Banion, Capone, Margaret McCarthy, and other characters broaden the story beyond a simple gangster adventure.
The book becomes most interesting when Aiden realizes that surviving the criminal world isn’t the same thing as building a life. His relationship with Sophia Golino gives that conflict real weight. As their romance develops into an engagement, pregnancy, and eventually marriage and parenthood, his decisions stop affecting only him. His increasing discomfort with killing feels especially important because the novel doesn’t suddenly turn him into a saint. He’s capable of violence, he knows how to bargain, and he can think like a gangster when someone threatens his family. Yet he gradually understands what continuing in O’Banion’s world will cost. The confrontation with Capone at the Golino home brings that tension to a satisfying peak. Aiden has the opportunity to kill Capone but chooses a bargain that lets him escape with Sophia and Celia. By the final chapter, his life in Berwyn with Sophia and their son Pietro gives the story a surprisingly domestic conclusion. Fatherhood, steady work, faith, and family become Aiden’s new measures of success.
A useful comparison is F. Scott Fitzgerald’s The Great Gatsby, another novel shaped by the money, ambition, and illegal liquor of the Prohibition era. Fitzgerald looks at the period through wealth, image, and social status, while Bootlegger’s Apprentice spends more time inside the machinery that helped make that world possible. Aiden sees the violence, political corruption, and personal compromises behind the glamour of speakeasies and easy money. Like Gatsby, he’s drawn toward a life that promises excitement and opportunity, but his story ultimately becomes less about chasing status and more about deciding what kind of future is worth having. That gives Broeren’s novel a grounded coming-of-age quality beneath its gangsters, gunfights, and historical detail, and it makes Aiden’s final turn toward family and stability feel like the natural conclusion to everything he’s learned.
Pages: 350 | ISBN: 0997776129
