His voice actor is Sonny Marinelli.
Henry Tomasino was born in Sicily to a life of crime, Henry's father was a member of the Sicilian Mafia who later died in prison. Henry was forced to leave Italy due to fears that he would be either drafted into the army or imprisoned as a result of Mussolini's crackdown on the Mafia.
Arriving to the United States in 1931, Henry came under the protection of the Clemente family in Empire Bay and soon started working with them.
Henry works with the Clemente crime family of Empire Bay, he has for a majority of his life, but it all changed once long time friend Joe Barbaro invites a new guy into the Falcone crime family, Vito Scalletta, Vito is a tough guy WWII veteran who has been in smaller, non mafia crime gigs with Joe. In 1945 Henry's mob leader, Clemente, gets Vito arrested and sent to prison on a count of armed robbery. Vito is locked up until 1951, after his release he seeks revenge on Clemente for locking him up. Once again Joe and Vito are the avengers of Vito's 6 year sentence. During a meeting at a hotel Vito and Joe disguise themselves as cleaners for the room where Clemente and other supreme leaders of the family are meeting. They plant a large bomb in the room. After a daring ecape, Vito and Joe successfully kill Clemente and everyone else in the meeting. Days after that, Henry is scared since his whole crime family got blown away, so he joins up with Vito and Joe in the Falcone family, however, once joining this family he gets into some things that the Falcone crime family or any other family would never be apart of, drug dealing. He begins dealing Heroin to make more money. Despite playing it safe in dealing the dope, it catches up with him. The Falcone family didn't know he was dealing, but a very large Asian gang does.
On September 24th, 1951, Henry calls Vito to meet him at Lincoln Park. When Vito and Joe arrive, Henry is stabbed to death by a group of Triad members in broad daylight, who are immediately shot and killed by Vito and Joe just seconds later.
It is later strongly implied and confirmed by Mr. Wong that Henry Tomasino was a federal informant - which is why the Triads killed him. Vito and Joe find this information hard to believe, before Vito inquires about the ambush at the factory days prior - which Mr. Wong said he used as an excuse to get rid of them as they both had problems since the beginning. When Vito asks for the money from the Heroin they sold, Mr. Wong tells them that he doesn't have it and cannot reveal who does. Irritated and out of options, Joe decides to shoot Mr. Wong fatally in the head.
Sometime later, Vito is visited by Leo Galante who tells him to get in the car with his associate Mr. Chu. Leo angrily explains that because of his and Joe's actions, Vito has caused a war within the Triads and the Commission. Leo also confirms that Henry was a rat, which justifies the actions of the Triads. Despite Leo's emotions, he offers Vito to kill Carlo Falcone.
- Henry is a devout Catholic, as suggested by the claim that he goes to church every Sunday.
- Additionally, he immediately recognizes a line from the bible quoted by Bruno as "Exodus, Chapter 22. Verse 24."
- After Henry's death, the news report claims he was a "struggling entrepenuer with interests in waste disposal and construction"