In Empire of Sin, it’s all about being the boss. Being the big cheese comes with its perks, but it also brings a whole lot of responsibility. Rackets, gangsters, rival gangs - the boss has to manage them all. Picking which boss you want to use to take over Chicago is the first choice you’ll make upon starting the game. Each boss has their own personality, specialities, combat abilities, and unique missions. From the free-wheeling glitz and glamor of Goldie Garneau to the stoic, cold violence of Salazar Reyna, each boss allows you to play the game in your own way. A detailed break-down of each individual boss can be found in Appendix.



None of the bosses are blank slates - they’ve all come to Chicago with long histories behind them, and what they’ve been through has affected who they are today. Each boss has traits decided by their background. For instance, Frankie Donovan’s battles and losses in the Irish War of Independence have made him Brave, which increases his Initiative in combat while outnumbered. Each boss has their own mix of traits, and getting to know how those traits affect their performance is key to utilizing them effectively.


A boss’s background isn’t the only thing that defines their traits, though. The scrapes and antics you get up to while conquering Chicago affects them just as much. Becoming more notorious in the city will give you an infamous presence, allowing you to hire more adept gangsters, but it will decrease your relationship with the cops. However you act is going to affect you in the long run, for better or worse. Traits can be found on the Gangster sheet. A breakdown of all Traits and their effects can be found in the Appendix.

Manual boss traits.png


Not all bosses are created equal. While every boss knows how to run the same kinds of rackets, each has their own specialities, and more specifically, two specialities. These give boosts to two different kinds of rackets. Daniel McKee Jackson’s made his bones off the brothel and casino games, and therefore has a 25% decreased chance of his brothels being raided by the feds. His casino bonus ensures that he earns an additional 20% cash in his gambling joints.

Each boss also has their own Diplomatic Bonus as a way of dealing with other gangs. Mabel Ryley’s slick Cork talk gives her a 10% extra chance for her trade agreement suggestions to be accepted, while Goldie Garneau’s exuberant manner reduces threat generation in neighborhoods shared with other gangs. Leverage your Empire and Diplomatic Bonuses to give you the edge against the other bosses.

Combat Abilities[edit]

While it can be useful to have your boss remain in their safehouse and run their empire from above, they can be deadly in combat (particularly in the early game, before you have a chance to build up a decent sized crew). Each boss has their own powerful unique abilities. These abilities have long cool-downs, but can completely change the direction of a tense shoot-out. Sai Wing Mock can throw three poison bombs at his enemies, dealing massive damage on impact as well as poison damage over time, while Maggie Dyer can use her whip to draw a target to her and hit them with a devastating punch. Your boss can be a huge benefit in combat. But remember: if they die, it’s Game Over.


You can’t breeze around Chicago knocking down rackets and murdering your rivals without drawing some attention to yourself. Performing certain actions, like killing thugs or guards, completing missions, recruiting gangsters, getting rackets, and so on grants you notoriety. As you gain notoriety, you won't have to pay so much for upgrades, and the thrill of being in such a dangerous boss's racket will even have your customers spending more money. Better yet, the higher your notoriety, the better class of gangster you’ll be able to recruit to join your crew.


Bosses share the same combat and social stats as other gangsters in the game, but a boss’s Intimidation, Leadership and Persuasion stats affect dialogue, sitdowns with other bosses and the outcome of some events. Combat stats are described in detail in the Combat section.

Manual boss stats.png

Hit Points[edit]

Bosses have significantly more hit points than most other gangsters and goons you’ll be facing across Chicago - you don’t get to be the boss without being able to take a few hits.

List of bosses[edit]

  Boss Heritage Biography Background
Profile boss Al Capone.png Al Capone Flag SalernoAmerican.png Italian-American You are notorious, just in from Brooklyn. You've mastered the ins and outs of the criminal world. Now that you've shaken off the shackles of your former cohorts, you're ready to dominate Chicago. The child of immigrants from Salerno, Capone worked hard from childhood to put food on the table. His meteoric rise to gang leader has left him happy, if a little reckless. He maintains his power by allowing no disrespect.
Profile boss Angelo Genna.png Angelo Genna Flag Italian.png Italian A mastermind of both political maneuvering and moving hot goods, you have a grip on Chicago that's nearly become a stranglehold. You won't stop until you've demolished your enemies and dominated the city. An immigrant from Sicily, Genna split his youth between hard labor and delinquency. With an angry fire in his belly like many young men, the only thing holding Genna's ambition back is his inexperienced naiveté. He prefers to shoot first if things start to go south.
Profile boss Daniel McKee Jackson.png Daniel McKee Jackson Flag American.png African-American You are generous and empathetic towards the downtrodden in Chicago. You are politically ambitious and a catalyst for change. Secretly, you operate one of the most profitable casinos in all of Chicago. Daniel McKee Jackson stuck through strict schooling to complete his education despite the years of poverty he endured as a youth. He used his cunning to pull himself out, and his kindness to pull up the rest of his community. He values discretion in all his activities over all else.
Profile boss Dion OBanion.png Dion O'Banion Flag IrishAmerican.png Irish-American You may run a flower shop, but you're anything but delicate. With your powerful international connections and your strong base on the Irish North Side, you're ready to claim your piece of the city. Born to Irish immigrants, O'Banion's faith does little to hold back his anger or cruelty. A delinquent from an early age, he cares about little but getting paid, no matter what he has to do to get it.
Profile boss Elvira Duarte.png Elvira Duarte Flag Mexican.png Mexican You are a queen atop a criminal empire that spans the city of Chicago. What you lack in brawn, you more than make up for in brilliance and bullets, and you provoke a fierce loyalty in those you employ. A former gang leader in Mexico, Duarte fled to Chicago to start her empire anew. Having seen it all, nothing disturbs her calm demeanor. It is lonely at the top, but that suits Elvira perfectly. She's seen many empires fall due to loose lips, and survives through her dedication to discretion.
Profile boss Frank Ragen.png Frank Ragen Flag IrishAmerican.png Irish-American Your dirty money has lined the pockets of so many politicians, police chiefs, and city treasurers that you might as well run the city yourself. You plan to claim the city using a deft combination of votes and vice. Ragen's Irish immigrant parents managed to instill a sense of religion in him, and not a whole lot else. He channeled his cruelty and intolerance into boxing as a young man, and now he pumps it into building up an empire. He relies on drawing like-minded individuals together.
Profile boss Frankie Donovan.png Frankie Donovan Flag Irish.png Irish Hailing all the way from Ireland, you are a five-time marksman, fearless in combat, and incredibly cool under pressure. You came to Chicago to make a name for yourself, and nothing will stand in your way. Donovan was forced to come to America in the aftermath of the Easter Rising in Ireland in 1916, where he lost a brother. He fell in with the Cause after completing his schooling, and its outcome has left him angry, though brave. It hasn't dulled his fun-loving, flirty side, though, because Frankie can bounce back from anything.
Profile boss Goldie Garneau.png Goldie Garneau Flag FrenchCanadian.png French-Canadian You're the talk of the town. You run the most exotic and popular speakeasy in Chicago. Outwardly you appear frivolous and carefree, but underneath you are calculating every move. You won't stop until you're running the whole city. Goldie was raised in Quebec, where she graduated from an incredibly repressive school. The school did little to repress her happy, flirty personality and her rebellious streak led her into a life of glitz and glamor. She is more of a lover than a fighter.
Profile boss Joseph Saltis.png Joseph Saltis Flag Hungarian.png Hungarian Your bootlegging prowess, diplomatic nature, and sincere attempt at appearing refined endears the community toward you. You're ready to graduate from bar owner to business magnate and take control of the city. Emigrating from the Austro-Hungarian Empire as a youth, Saltis worked as a child laborer before turning to crime to make some real money. He never lost respect for hard work. He started his own gang, and developed a taste for the finer things in life. His careful, cunning attitude has steered him well in Chicago.
Profile boss Mabel Ryley.png Mabel Ryley Flag Irish.png Irish You are simultaneously vicious and kind. You've inherited control of the Alley Cats from your (now deceased) husband and you have your sights set on gaining control of the rest of Chicago. Immigrating from Cork, Ireland, Ryley spent her youth avoiding her strict schooling and engaging in delinquency. Growing up without much, she takes an "easy come, easy go" approach to life. She gets ahead by remaining calm and careful in all matters.
Profile boss Maggie Dyer.png Maggie Dyer Flag American.png American It doesn't take much for you to get what you want, either through pure intimidation or delicate persuasion. After years of managing the circus, you're ready to run a new menagerie of criminals and cohorts here in Chicago. Raised in poverty, Dyer dropped out of reform school to work at the White City Circus. Those early years of misfortune have made her sullen, but brave. After running the circus for so many years, she knows that everyone has their price.
Profile boss Sai Wing Mock.png Sai Wing Mock Flag Chinese.png Chinese-American You are bold, proud, and unflinching in your quest for dominance in Chicago. Just in from Chinatown, New York, you are determined to take control of all this city has to offer. Sai Wing Mock arrived on the west coast as a young man, the child of a devoutly religious Chinese family. His calm and cunning nature led him to become a feared gang leader within the Hip Sing Tong. He gives nothing away for free, saying as little as possible.
Profile boss Salazar Reyna.png Salazar Reyna Flag Mexican.png Mexican All the way from Oaxaca, Mexico, you're in Chicago for two things: money and glory. You don't flinch from brutality and will kill to get your way if you have to. You're an unstoppable force, demolishing everything on your path to get to the top of Chicago. A bloody incident out west in Los Angeles has made Reyna into a sullen loner, determined to place his trust in no one. Originally a boxer from Mexico, he was forced to flee to America in his youth.
Profile boss Stephanie St Clair.png Stephanie St. Clair Flag French.png Martiniquais Ferocious and fearless, there are few in Chicago who would dare defy you. You came to Chicago to conquer, as you did in New York. And you don't care who gets in your way. Stephanie fled the West Indies and established herself as the Queen of Harlem through her cunning, tolerance, and with faith in the people around her. She lives by the mantra that no man (or woman) is an island.
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