- "This is a high risk business. If you don't like it, you can always go break your back working for peanuts down at the docks."
- — Henry Tomasino
Henry Tomasino was a Soldato in the Clemente crime family. He was involved in running fronts for Clemente, such as his meat packing business, as well as labor rackets at the Southport docks. He helped Vito Scaletta and Joe Barbaro immerse into Empire Bay's criminal underworld and later joined the Falcone family after Clemente was killed.
Henry was the son of a Sicilian mobster, along with his six brothers. He was sent to America in 1931 to escape Mussolini's clampdown on the mafia, and because of his father's fear that his son would either be drafted into the army or imprisoned. In Empire Bay, Henry came under the protection of Alberto Clemente, an old family friend.
Not much is really known about Henry as he didn't talk about himself or his life very often and he had few friends. He was very knowledgeable about the various criminal organizations in Empire Bay but he was different from the other mobsters he worked with, being very level-headed, proper, and refined; he was an old fashioned man of honor.
Vito is introduced to Henry by Joe in Enemy of the State, where Henry asks Vito to steal some gas stamps from the Office of Price Administration. Vito does so successfully, but Henry finds out that they expire the next day. He then tells Vito to sell the gas stamps to gas stations before midnight. He is next seen in Murphy's Law, and on orders of Luca Gurino, Henry asks Joe and Vito to rob a jewelry store owned by someone who owes money to Don Clemente. The robbery doesn't quite go according to plan, as Brian O'Neill and his gang also try to rob the store. After an intense shootout with the Irish mob as well as local law enforcement, Vito and Joe escape with the jewelry. In The Buzzsaw, Henry is given a contract by Luca Gurino to kill "The Fat Man". Henry asks Vito and Joe to act as backup and tells Vito to go to Harry's Shop to pick up an MG-42. The hit goes successfully until Henry gets shot in the leg by Pen. Pen is then gunned down by Vito and Joe. The two men take Henry to El Greco for medical assistance. After Vito goes to jail, Henry feels guilty and wants to repay Joe, so he warns him that Luca has put him on his hitlist.
Henry isn't seen again until Room Service, where he and another Clemente soldier are taking a beaten-up guy out of the Empire Arms Hotel. However, Vito and Joe avoid his attention and successfully assassinate Alberto Clemente and his top men. Henry then meets up with Vito and asks him to vouch for him and help him get into the Falcone family. Henry is asked to kill Leo Galante to earn his place in the family. However, Vito helps Leo escape to Lost Heaven and Henry is still welcomed into the Falcone family. Henry convinces Joe and Vito to enter the drug trade with him, and they borrow money from Bruno Levine, a loan shark with connections to the mafia. In order to do so, they buy several kilos of heroin from the Empire Bay Triads. However, some unknown assailants in police uniform ambush the trio but they escape and get back into drug trade.
On September 24, 1951, as Vito and Joe approach Lincoln Park to meet with Henry, they see him on the ground being attacked with meat cleavers by several Empire Bay Triads. Though Vito and Joe stop the attack, they're too late and Henry dies of his injuries. Vito and Joe follow the remaining Triads, along with Zhe Yun Wong, to his base of operations at The Red Dragon restaurant.
After killing all of Wong's men, Vito and Joe confront him in his office and at gunpoint, ask him where their money is and why he ordered Henry's death. Wong claims that his contact at the Federal Bureau of Narcotics informed him Henry was an informant but refuses to say where the money is. Joe then shoots Wong in the head, killing him and avenging his role in Henry's death. When they drive to Joe's apartment, Joe doesn't seem to believe Henry was a rat and says he doesn't even want to hear about it.
- Silvio Tomasino (father, deceased)
- Eleonore Castrogiovanni (mother)
- Bettina Canavosio (wife, deceased)
- Basilio Tomasino (brother)
- Fausto Tomasino (brother)
- Manfredo Tomasino (brother)
- Osvaldo Tomasino (brother)
- Pietro Tomasino (brother)
- Salvatore Tomasino (brother)
- Enemy of the State
- Murphy's Law
- The Buzzsaw
- Room Service
- A Friend of Ours
- Sea Gift
- Exit the Dragon (Killed)
- Witness - Frozen Memories (Joe's Adventures)
- Henry was one of the "wiseguys" that Joe and Vito idolized when they were children.
- He frequents Freddy's Bar, which is the front of operations for the Clemente family.
- According to Frankie Potts' files, he has several addresses, but he mainly lives at the Empire Arms Hotel.
- He goes to church every Sunday, suggesting that he is a devout Catholic.
- Henry may be a distant relative of Frank Vinci, as Vinci's mother's maiden name is Tomasino.
- His thirteenth contract was to kill the "Fat Man". He believes this is the reason he got shot, as the number thirteen is associated with bad luck. Coincidentally, his death occurs in Chapter 13.
- It is mentioned in the family album that his only motivation is his pride and loyalty, and this is what he is known for by the Mafia.
- One news report after his death said he was a struggling entrepreneur; another claims he had interests in waste disposal and construction.