New York City, 1896. After barbarously stabbing a friend of his named Edwin Band in a fight, the police officers believed that he, blinded by bloodlust, had also killed Giorgio Santorelli, "the Boy on the Bridge." Dr. Kreizler asked if anyone else had questioned Wolff, besides the police, but Dr. Fuller replied that someone had tried but Wolff almost ripped his eyes out.
He was repeatedly banging his forehead against the corner of the cell, causing himself deep wounds while Dr. Laszlo Kreizler and John Moore came visiting him. Ignoring the cries of the other inmates, Dr. Kreizler asked Mr. Wolff what he hoped to achieve through similar "exercises." When Wolff approached the bars, revealing a face horribly disfigured by sores, the alienist replied that there was no cure for the advanced stage of syphilis. Dr. Kreizler investigated the reasons that led Wolff to kill his friend, Edwin, inquiring him to kill the boy too. Addressing the Paresis Hall, however, Wolff snorted, stating that he was not accustomed to "molly houses full of rich pansies." Following Wolff's sexual allusions to John Moore, Dr. Kreizler asked Mr. Wolff if Moore reminded him of his friend Edwin, triggering a crisis in the suspect, who shouted he would kill him again if he could. The alienist continued his inquiry, ordering the guard to open the cell to approach Henry Wolff, despite John's advise not to do it. Once there, he was able to make the suspect confess he had nothing to do with the murder of Giorgio Santorelli since Edwin Band's murder was a crime of passion. Upon leaving, Wolff asked Kreizler what will catch him first between the gallows or the pox, to which the alienist replied he was afraid that in the New York State it would be the electric chair. "Either way, his pain will be gone soon." 
Days later, Miss Sara Howard was gluing some newspaper clippings into a journal at the New York City Police Department, including one called "Wolff cleared in Santorelli murder" but still pending trial for the murder of Edwin Band, most likely resulting in a death sentence. 
Appearance and PersonalityEdit
Henry Wolff is a handsome man with broad shoulders, green eyes, and brown hair. Following the contraction of syphilis, his face and part of the rest of the body has become disfigured by painful sores. During his imprisonment in a solitary confinement cell at the Bellevue Hospital, he became increasingly angry and suffering because of his illness, repeatedly slamming his face against a corner of the wall, severely injuring his skull. Heavily-tempered and easy to fits of rage, Wolff is a very rancorous man who killed in cold blood what he seems to be, according to Dr. Laszlo Kreizler, his former lover who had abandoned him following the contraction of syphilis. In spite of this, Wolff has used derogatory terms against the prostitutes of the Paresis Hall, a well-known brothel for homosexuals, either in an attempt to throw off allegations of homosexuality or for a previous internalized homophobia.
- Henry Wolff (to Dr. Kreizler): "Edwin deserved it!I'd kill him again if I could."
- Dr.Kreizler: "The boy? You're accused of cutting him to pieces. Police said you knew him from Paresis Hall."
- Henry Wolff: "Do I look like a boy to you? I wouldn't step foot in that molly house full of rich pansies."
- Henry Wolff (to John Moore): "What are you looking at? Do I stimulate you?"
- Henry Wolff "Doctor? What'll take me first the gallows or the pox?"
- Dr.Kreizler: "I'm afraid in New York State, it'll be the electric chair. Either way, your pain will be gone soon."
- — The Boy on the Bridge
- In the novel by Caleb Carr, Henry Wolff is interviewed by Dr. Kreizler and John Moore at Bellevue Hospital for the murder of his neighbor's daughter, Louisa Rudesheimer. In the TV adaptation, however, he is interviewed for the murder of his friend, Edwin Band with the hint of the two of them being former lovers.