The Calabrese Family

The Calabrese Family is the central, ruling family of the infamous La Famiglia Nostra crime syndicate. They oversee the actions of the criminal organization much in the same way that a royal family might oversee its kingdom. Claudia Calabrese is the current matriarch of the family and the acting Donna of La Famiglia. All of La Famiglia's cadet families swear an omerta - an oath of honor and loyalty - to the Calabreses, swearing to protect them from all harm and promising them a portion of their profits.

Claudia Calabrese
The matriarch of the Calabrese family and acting Donna of La Famiglia Nostra. See Claudia Calabrese.

Vincentio "Vinny" Calabrese
The founder and former Don of La Famiglia Nostra. See Vincentio Calabrese

Enrico Calabrese
Vincentio's oldest son by his first wife, Antonia. As a child, he went by the nickname "Rico" but has since grown out of it and prefers his full name. Enrico is 37 years old and happily married to Lucia Bianchi, the daughter of Vincentio's lifelong friend Diano. He has two young children, Roberto and Henrietta, whom he loves dearly.

Enrico was favored by Vincentio to take over La Famiglia Nostra as the Don one day. A calm, stoic, composed, and dispassionate man whose politeness belies deep-seated cruelty. He is civil to Claudia, but has never regarded her as a mother figure. He treats her like a reasonably friendly acquaintance rather than a parent. Currently in prison and awaiting trial.

Ceasario Calabrese
Ceasario is the second oldest of the Calabrese children, age 33. Nicknamed "Ceasar" or sometimes "CeCe" by very close friends or family. Ceasario married Angelica De Luca - the daughter of former underboss Christian De Luca - shortly before he was arrested and imprisoned by the Streetsweepers. Angelica, however, recently filed for divorce after the De Luca cadet family decided to break omerta and split from La Famiglia. They have no children.

Ceasario is very similar to his father both in looks and temperament. He was Vincentio's favorite son and the two had a close bond with one another. However, Vincentio preferred for Enrico to be his successor - both because Enrico is the eldest and because of Enrico's stoic temperament. Ceasario is far more volatile. One minute, he’s friendly, boisterous, funny, and warm. The next minute, he’s moody and liable to snap over any perceived slight. Ceasario wanted to take over the mob and is open in his resentment toward his elder brother Enrico.

Ceasario has always disliked Claudia and the two frequently butted heads when they were under the same roof. Currently in prison and awaiting trial.

Alphonsus Calabrese
The third and youngest of Vincentio's sons with Antonia. Alphonsus is thirty years old and unmarried, though he had an arranged engagement with Giovanna Endrizzi before she died. He often goes by the nickname "Alphie" or just "Alph." Alphonsus is athletic, handsome, charming, easygoing, though perhaps a little vain and sometimes a bit lazy. He's fine with being the third son and riding on his brothers' coattails. He's not especially ambitious. Currently in prison and awaiting trial.

Alphonsus was only three when his mother died and does not remember her well. He is the only one of Claudia’s stepsons to bond with her. He thinks of her as his legitimate mother and they have a good relationship with one another. Alphonsus is also close with his two younger siblings, despite their difference in age.

Mattheo Calabrese
Mattheo (often called "Matty") is the oldest son of Claudia and Vincentio Calabrese. He is 23 years old and currently attending Harvard University in Cambridge, Massachusetts for his law degree. Notably, he's attending the Ivy League school on a scholarship for his excellent academic performance and needs no financial support from his family. Mattheo has ambitions to become a lawyer and provide assistance to immigrant families in need. Mattheo is open about his disdain and disinterest in the family business. He's the first Calabrese son who desired to "go straight" and make a legitimate living for himself. However, his goals are now in danger due to the fact that he's currently the oldest male Calabrese alive and out of jail. Mattheo would prefer for his mother and sister not to be involved in the business, but at the same time, he's somewhat content to let his mother run the show while he lives his life quietly in the background.

Mattheo is a studious young man who has difficulty socializing and forming friendships. He has never had a girlfriend. Mattheo Calabrese would mostly just like to be left alone, to go through life at his own pace and not be burdened by the expectations or demands of other people. He doesn't really experience loneliness as others do. To be ignored or overlooked is a relief for Mattheo. If he had his way, he would like to be invisible -- only appearing to those he cares about and disappearing from the notice of everyone else. Many people see him as rude and standoffish, though most of his rudeness is unintentional. He's also emotional and quick to anger -- another quality that makes it difficult to form lasting friendships. He snaps at people who annoy him quickly, which can create a bad first impression.

Giulietta Calabrese
Giulietta Calabrese grew up as the only daughter of the wealthy and infamous Calabrese family. Giulietta has a willowy, slender frame like her mother with a head of curly dark hair and warm grey eyes. Since her kidnapping at the hands of the Endrizzi family, she has an X-shaped scar on her right cheek. Friends and family often note the startling resemblance between Giulietta and her mother, despite their differences in coloring. Giulietta is sixteen years old and attends St. Mary's Preparatory Academy, a prestigious Catholic single-sex private school. In terms of personality, Giulietta is known to be warm, friendly, affectionate, emotional, silly, and willing to start a conversation with just about anyone. Due to her extremely sheltered and privileged upbringing, however, she can be short-sighted, naive, and a little cruel - often acting younger and more immature than her age. Giulietta cries easily, is very spoiled, and sulks when she doesn't get her way, but she's also vivacious, energetic, and not easily discouraged.

Giulietta has solid and positive relationships with most of the Calabrese clan. She gets along well with her older brothers Mattheo and Alphonsus. Enrico and Ceasario mostly ignore her, to her consternation. Giulietta considers her mother, Claudia, to be her best friend and they're frequently seen together. It's not uncommon to see Giulietta clinging affectionately to her mother's arm or to see them cuddling closely on the sofa. Giulietta is one of the few people that Claudia is openly tender and gentle toward. Giulietta also had a close and highly protective relationship with her father prior to his death -- and losing him broke her heart. Vincentio considered Giulietta one of his favorite children and endeavored to protect her from the uglier aspects of his business. She has been dating Cirillo Fiorentino on-and-off for roughly three years throughout high school and the two are expected to marry when they get older.

Iona Calabrese
Iona Calabrese is Vincentio's mother. She lives in Sicily in a villa purchased for her by her son. The Calabreses visit her every few years for Christmas. She speaks no English.

Lucia Calabrese
Enrico's wife and the daughter of Diano Bianchi. Lucia is a kind-hearted and traditional woman whose focus is on motherhood and supporting her family. She's good friends with Claudia.

Roberto Calabrese
Enrico and Lucia's son - age 6. Calm and thoughtful like his father.

Henrietta Calabrese
Enrico and Lucia's daughter - age 2. Sweet, gentle, and adorable.

Antonia Calabrese
Vincentio's first wife - a traditional Sicilian woman who preferred to focus on taking care of her family. She originally immigrated with him from Sicily and spoke little English. She was devoutly Catholic and strongly disapproved of her husband's work. Antonia disappeared abruptly after contacting the Chicago Police Department with a promise of information about her husband's activities. It's believed by most that Vincentio killed her, however it was never proven and the case remains cold to this day.

Gabriella Calabrese
Gabriella was Vincentio's sister. She immigrated to America shortly after him and married Samuele Esposito - an underboss of La Famiglia and a friend of her brother. She unfortunately died in her 30's due to complications with her son Roman's birth. Gabriella's passing was considered a massive tragedy for La Famiglia.

Fillipo Calabrese
Fillipo Calabrese was Vincentio's father and the husband of Iona. He died when Vincentio was young, leaving Vincentio to care for his sister and mother.

Henry Scaglione
Henry Scaglione is Claudia's personal driver and bodyguard. He's also assigned to protect and monitor the younger Calabrese children, Mattheo and Giulietta. Henry is a soft-spoken and outwardly somewhat shy man. However, the truth is that Henry Scaglione is a deadly fighter with years of martial training and a history of service in the United States Military. Henry was personally responsible for the deaths of Eduardo Endrizzi and Bartolomeo De Luca after they kidnapped the Calabrese children. He's extremely well-paid and for good reason.

Bridget O'Driscoll
Bridget is Claudia's housekeeper, chef, and maid. She's a young woman in her twenties -- plump and pleasant with reddish-brown hair and dense freckles across her pale Irish complexion. Claudia hired her after her husband's passing. While Bridget is aware of the family's criminal dealings, she is not involved in any mob activity herself. Bridget knows her place and tries not to overstep her boundaries as an employee. Despite the fact that Bridget has never sworn an omerta, she is very loyal to the Calabreses and especially to Claudia. Bridget would rather die than betray her employers to the police. She's currently in a romantic relationship with Armando Bianchi.

Daniel Sullivan
Daniel Sullivan is a well-known lawyer in Chicago whom the Calabreses keep on retainer. He’s the founder and primary partner in Sullivan & Sons Legal Firm. He earned Vincentio’s friendship after getting him off the hook for his first wife Antonia’s murder. Over the years, he’s formed a bond with Claudia and her family. Currently, he’s working on getting the imprisoned underbosses and the eldest three Calabrese sons out of prison - an enormous undertaking that requires equally enormous legal fees which Claudia is all too happy to keep paying.

Despite being married faithfully to his wife for many years, he has a somewhat flirtatious relationship with Claudia. He normally brings her flowers whenever they visit one another. Claudia affectionately refers to him as “darling Danny.” Their relationship has never progressed beyond some harmless flirtation, though.

Norma Scaglione
Henry's wife and the manager of La Primavera, the Calabrese's restaurant.

The Calabrese Waste Collection Agency
Many mobsters under La Famiglia Nostra have "legitimate" jobs with Chicago's commercial sanitation system. The sanitation jobs allow them to patrol certain segments of the city and extort small businesses in their controlled districts under cover. The Calabrese family owns a private waste disposal business (the Calabrese Waste Collection Agency) through which they launder their ill-gotten drug, prostitution, and extortion money. They have two offices - one on the North Side and one on Lake Side.

La Famiglia Nostra is deeply in bed with the Chicago Sanitation Worker's Union. In fact, it would be accurate to say that the Union and the Calabrese Waste Collection Agency are one and the same. Employees of the Calabrese Waste Collection Agency tend to be higher-ups in the Union as well. By working closely with the union, they've managed to secure large public contracts for the city government, drive out competition from other waste collection businesses, and also help install their people at city hall. The Calabreses fix the prices for trash collection in the city, rig bids for contracts so that no one else can make an offer, and lock down territory so that customers cannot choose who collects their garbage. Smaller collection companies are extorted or prevented from gaining union membership by the mob.

Claudia Calabrese is an advocate for the rights of sanitation workers throughout the city - pushing for greater wages, fewer hours, and better working conditions. She uses her position as a means to smear other waste collection agencies and drive them out of business by accusing them of abusing their employees - or publicly applying pressure to raise wages so high as to make business unsustainable for competition. She also makes a big show of support and generosity toward employees (in actuality - fellow mobsters) of the Calabrese Waste Collection Agency, making their company appear more virtuous in comparison to the competition.

Though it's a well known fact that the Calabreses are a corrupt force in Chicago's waste collection, it's been difficult to prosecute them. Evidence of their illegal dealings is thin on the ground. Competition is threatened into silence or suffer "accidents" if they try to go public with what the Calabreses have done. The fact that so many mobsters are also sanitation workers provides a cover of plausible deniability for many acts of extortion and intimidation. The fact that the Calabreses control the dumps also means they have a convenient method of disposing of evidence/bodies in the event of an investigation. Complaints against the Calabrese Waste Collection Agency are often quickly silenced by the union and/or allies in city hall. Claudia and her higher-ups also make a point of never harassing, threatening, or harming competition directly - almost always acting through various proxies that can take the fall if discovered.

La Primavera
La Primavera is an Italian restaurant on the North Side owned by the Calabreses, within walking distance from the Lexington Hotel. It's a known mob gathering location and speakeasy. Regulars report that the food is actually very good, though, with menu items based on recipes from Vincentio's mother, Iona Calabrese. Menu items include spaghetti carbonara, puttanesca, osso bucco, malfatti with tomato sauce, cannolis, tiramisu, to name a few. (And, of course, it wouldn't be Chicago without pizza, would it?)

The restaurant features vaulted, brick ceilings supported by rows of thick, sturdy columns and hardwood floors. Multicolored mosaics decorate the vaults, depicting scenes of the Italian countryside - such as a dark haired milkmaid washing in a stream as a mischievous fox steals her hat, or a shepherd with a crook watching his lambs from beneath the shade of a blooming cherry tree. Wall sconces and dangling chandeliers illuminate the vaults - their light low and romantic. Bucolic paintings hang upon the walls.

Windy City Children's Foundation
A foundation for the benefit of underprivileged children, run by Claudia Calabrese. The Windy City Children's Foundation was founded by Claudia in the 1910's to aid victims of childhood poverty, abuse, addiction, or neglect (conveniently ignoring the fact that La Famiglia's rum-running and drug dealing directly contributes to those things). The Windy City Children's Foundation provides scholarships for students to attend private schools and college, as well as offering aid to meet the basic needs of children, especially immigrant children, in poverty. The foundation can be something of an ouroboros with La Famiglia, providing a nice cover to launder money as anonymous donations. Not to mention grateful parents can be coerced into working for the mob, lest their children's scholarships and much-needed aid be suddenly taken away.

Apartment Buildings
The Calabrese family also three apartment buildings - one on North Side and two on Lake Side. The North Side apartments are nicer and frequently rented to government workers from city hall. The Lake Side apartments are rented to workers or mobsters laboring in the port or the warehouse district, with their rooms also occasionally used for prostitution.