Leo D'Alessio (played by Max Casella) is a Philadelphia criminal who tries to muscle in on bootlegging through Atlantic City. He leads a gang of criminals consisting entirely of his own family. They are known as the D'Alessio brothers. He, along with his brother Ignacious are the secondary antagonists of the first season.
Leo is a Philadelphia based criminal involved in assault, extortion, gambling and loansharking. He works with his brothers Ignacious, Sixtus, Matteo, Lucien and Pius. Leo is the second oldest of the brothers after Ignacious. Ignacious and Leo are the leaders of the group. He has another three brothers and five sisters - thirteen siblings in total. Prior to Prohibition, Leo served a 3 year prison sentence for assaulting a police officer.
Bootlegger Mickey Doyle is led into a diner in heavy rain by Pius D'Alessio. He is met inside by Leo and Ignacious D'Alessio. Pius reports that Mickey was waiting outside and Mickey claims that he was given the wrong address. Leo jokingly asks if it is raining and Mickey responds that he almost drowned, amusing Ignacious. Mickey pours himself a drink and thanks the brothers for bailing him out. Mickey asks where they are staying and finds out they are in a flop house on Baltic Avenue. Leo claims the sea air is good for Ignacious’ respiratory problem but Ignacious admits the real reason they had to leave Philadelphia was his fifteen outstanding arrest warrants. Mickey asks Ignacious if he has a lawyer, mistakenly using the wrong name. Pius corrects him and calls him a Polack. Mickey points out that he has changed his name. Leo sends Pius to check on the car and Ignacious reminds Mickey of his name. Mickey jokes about the size of Italian families and Leo says there are 9 brothers. Ignacious interjects that their father loves their mother very much and places a pistol on the table. Mickey complains about Nucky Thompson giving “their operation” to Chalky White and Leo objects; pointing out that he loaned Mickey money with interest and Ignacious says that they are not partners. Mickey claims he thought they wanted an opportunity and that he needs a business to be able to pay them back. Leo calls this Mickey’s problem but Mickey convinces the D'Alessio brothers to help him to work off his debt. He plans to have them murder Chalky and gives them a description of Chalky's car, a Packard. They track the car but mistakenly lynch Kendall, Chalky's driver, instead of Chalky himself. ("Broadway Limited")
Mickey meets with the D'Alessio brothers at their flop house as Ignacious gets his hair cut by his brother Matteo D'Alessio. Mickey complains that they killed the wrong man. Leo reminds Mickey that he told them that Chalky drove a Packard so they killed the man driving a Packard and says that he believes they sent a message anyway. Mickey complains that Chalky is still operating. Matteo demands repayment of the money they loaned Mickey. Mickey has not been introduced so asks Leo which brother Matteo is. Mickey jokes that they are all named after popes and Matteo closes in and presses his scissors against Mickey’s neck. Leo reminds Mickey of his debt and Mickey agrees to pay. Ignacious asks how Mickey will get the money and Mickey offers to give the brother’s information that will earn them $3000. He suggests that they rob one of Nucky’s ward bosses as they make collections. Leo agrees with the plan but warns that he will hold Mickey responsible if it fails. ("Anastasia")
They next target Thompson's ward bosses, who Doyle has told them make collections for him. Ignacious and the youngest brother, Pius, follow George O'Neill while he is making collections. Pius incites O'Neill to chase him and Ignacious knocks him out and steals the money. Thompson suspects Lucky Luciano of the theft and questions him. ("Family Limitation")
The brothers play cards with Doyle in a darkened speakeasy in Atlantic City. Luciano enters with Meyer Lansky. Leo greets Lucky warmly and Lucky recalls that he last saw the brothers when they were arrested together. Ignacious introduces Doyle to Lucky and Lucky in turn introduces Lansky. Doyle offers his hand to Luciano but Lansky steps forward and takes it. Speaking in Italian Ignacious tells Lucky that Doyle owes them money and that he would slit his throat but wants to be repaid. Lucky jokingly responds that Doyle is the goose that laid the golden egg. Luciano, returning to English, tells Doyle that Ignacious has said that he is a reliable person and shakes his hand. Leo sends Pius to get hot drinks. Leo wonders why Luciano is in town; Luciano explains that he is there on business and Leo waves out the only other customer. Luciano asks them how many times they think they can rob Nucky’s collectors before Nucky retaliates. Pius hands out cups of coffee and tells Lucky that it was easy. Luciano smiles pleased that Pius confirmed his assumption. Matteo says that they are establishing themselves in bootlegging and needed start-up funds. Lucky says that $3000 is a nice amount and Mickey says that it is not hay. Luciano says that they owe Arnold Rothstein a cut for the privilege of operating and Doyle says that Rothstein has no jurisdiction in Atlantic City. Luciano finishes his drink and holds out the cup to a distracted Pius; Leo clicks his fingers to prompt the boy to take it. Lansky wonders if they have noticed rising gasoline prices. Matteo wonders who Lansky is, calling him a “kike.” Lansky repeats his name and Luciano repeats that Lansky is his friend. Lansky returns the subject to gasoline and Luciano explains that they need to buy gas to distribute their alcohol. Luciano and Lansky detail the other necessary overheads for a bootlegger; warehouse, stills, bribes for police and politicians, crates, bottles and labels. Lansky asserts that running a decent bootlegging operation will cost more than $3000. Ignacious counters that they have muscle and Leo puts a restraining hand on his arm. Lucky points out that they cannot fight a whole city themselves. Leo wonders if Lucky means that Rothstein is willing to back them. Luciano tells them that Rothstein wants to know that they are capable and gives them a task. He asks them to rob Lolly Steinman’s casino and tells them that they will need to give 50% of the expected $150,000 take to Rothstein in New York while Luciano says the rest will be used to fund further operations in Atlantic City together. Leo balks at the collective but shakes Luciano’s proffered hand. ("Home")
Ignacious, Leo and Matteo hold up the casino just before the evening's take is collected. Eli Thompson is responsible for the collection and when he arrives they surprise him. He is shot in the abdomen by Leo as he reaches for his gun. Pius is the getaway driver and the brothers escape with the money. ("Hold Me in Paradise")
Eli survives his wounds. Eli and Steinman are able to identify the brothers despite their use of masks. ("Belle Femme")
Rothstein plays pool in his games room in New York City. Lansky knocks and lets himself in, sharing a nod with Rothstein. Lansky is followed by Leo, Ignacious, Doyle and Luciano. Luciano introduces the others and they shake hands with Rothstein. Leo says that it is an honour to meet him; Rothstein notes that they have heard of him and wonders what it was that they heard. Leo says that it was all good. Rothstein wonders if he has a reputation for honesty and fairness and Leo says that he has. Rothstein tells them that a reputation takes a lifetime to build and seconds to destroy before completing a difficult trick shot. He asks Luciano to re-rack the balls and counts a few bills from his sizeable bankroll. He tells his visitors that he has heard that they are interested in the liquor business and Ignacious says that they are interested in making money. Rothstein challenges Luciano to a game of eight ball pool for $500. Luciano breaks as Lansky takes the wager. Rothstein says that are two ways to make money in the alcohol business, the first being to take cheap whiskey and dilute it before resale. Doyle interjects that he was doing well with that way and Rothstein continues calling this the stupid way which does not interest him. Rothstein notes the growing demand for quality whiskey and the money that can be made by importing it. He believes rich people will vie with one another to serve the best whiskey to their guests. Rothstein plays as he talks and sinks a succession of balls. He tells his guests that he is interested in setting up a business importing scotch whiskey. He plans to use his own ships to bring the liquor from distilleries in Europe to be unloaded outside the 3 mile limit. He explains that it then needs to be smuggled ashore and Lansky adds that this will be the D’Alessio brother’s role. Rothstein asserts that Atlantic City is perfect for this purpose but that Nucky is a problem. He says that he would normally make a deal with someone like Nucky but that he finds Nucky greedy and unreasonable. Leo notes that these are qualities that can be remedied with a bullet. Luciano smiles at the remark while Rothstein ignores it and asks his visitors to sign forms that he has prepared for them to signify their acceptance of his proposal. Leo wonders what the forms are for and Luciano elucidates. They are $500,000 life insurance policies from Rothstein’s own Rothmere Surety company. Rothstein adds that they will be handling large quantities of his money and that the policies are assurance for him. Luciano tells them to consider it an incentive not to make mistakes as Lansky hands them a pen. Leo and Ignacious are hesitant and Luciano urges them on in Italian. Leo, apparently lacking literacy skills, grips the pen at its base and makes his mark. Doyle joins the others and with the forms signed Lansky offers to show them out. Sixtus and Lucien attempt to kill Nucky on the boardwalk but Eddie Kessler saves Nucky's life and manages to shoot Sixtus in the leg as he flees. ("Belle Femme")
Leo also attempted to make a bootlegging deal with Chalky White.
Following the casino robbery, Luciano introduces Ignacious and Leo (along with Doyle) to Arnold Rothstein and Meyer Lansky. Luciano suggests that they could take over the bootlegging trade in Atlantic City and they agree to assassinate Nucky Thompson. Sixtus and Lucien are brought in to kill Nucky but their boardwalk shooting attempt is unsuccessful. Thompson responds by asking Chalky to contact Rothstein's organization through Lansky under the pretence of switching sides. Lansky, Matteo and Lucien meet with Chalky in Atlantic City. Chalky drops the pretense when he realizes the D'Alessio brothers killed his driver and takes all three of his visitors captive. Matteo and Lucien are killed by Thompson's people and the remaining brothers go into hiding. Rothstein and Thompson negotiate a peace deal that includes giving up the D'Alessio brothers. Jimmy Darmody cuts Leo's throat in a barbershop. ("A Return to Normalcy")
- Ignacious D'Alessio: Brother and partner in crime (deceased)
- Sixtus D'Alessio: Brother and partner in crime (deceased)
- Matteo D'Alessio: Brother and partner in crime (deceased)
- Lucien D'Alessio: Brother and partner in crime (deceased)
- Pius D'Alessio: Brother and partner in crime (deceased)
- Mickey Doyle: Criminal associate and debtor (deceased)
- Charlie Luciano: Criminal associate
- Meyer Lansky: Criminal associate
- Arnold Rothstein: Criminal associate (deceased)
- Nucky Thompson: Bootlegging rival (deceased)
- Chalky White: Bootlegging rival (deceased)
- Eli Thompson: Atlantic County Sheriff
- Lolly Steinman: Robbery target
- Jimmy Darmody: Murderer (deceased)
|Season one appearances|
|Boardwalk Empire||The Ivory Tower||Broadway Limited||Anastasia|
|Nights in Ballygran||Family Limitation||Home||Hold Me in Paradise|
|Belle Femme||The Emerald City||Paris Green||A Return to Normalcy|
- Morita, Drew (January 25, 2011). The Real Story Behind Boardwalk Empire's Al Capone. Examiner.com.
- The Efficient Drinker (September 21st, 2010). Boardwalk Empire Characters. The Efficient Drinker blog.
- Philly Gangster. Philly Neigbors.com.