Sally Tomato's imprisonment sets in motion two competing accounts of Holly Golightly’s visits to Sing Sing: to Holly, they are a weekly act of companionship for a pious, lonely old man; to the press and prosecutors, they make her a courier in an international narcotics ring. The gap between those accounts turns an apparently private friendship into the central accusation behind her arrest.

Background and Imprisonment

Holly recalls that she knew Tomato by sight before his imprisonment. He used to stand silently at Joe Bell's bar, around the corner, seeming to her like a man accustomed to living in hotels. After he was sent to prison, Joe Bell showed her Tomato’s picture in the paper. The news account identifies his sentence as five years for political bribery and presents him as a Mafia figure; Holly, by contrast, remembers an unobtrusive man she had seen without knowing him.

The sequence brings the jailed man’s public notoriety and Holly’s personal impression into uneasy contact. She says that, looking back, she realized how closely he must have watched her at the bar. The apparent intimacy of the prison relationship thus has a prior history of observation, but Holly insists that she did not know him until he was already incarcerated and denies that he had ever been her lover.

The Visits and Their Arrangement

After Tomato’s imprisonment, a telegram from a lawyer instructed Holly to contact him for information to her advantage. She initially suspected that Bergdorf was trying to collect from her, rather than imagining that someone had left her money. She took the gamble and met the supposed lawyer, who, she says, had no office beyond an answering service and preferred to meet at Hamburg Heaven. Holly’s description of his appetite—ten hamburgers, two bowls of relish, and a lemon meringue pie—makes the arrangement feel at once concrete and comic, while also casting doubt on his professional identity.

The lawyer proposed that Holly cheer up a lonely old man and receive a hundred dollars a week. She first rejected the offer, saying that she was not a nurse who performed sexual services on the side and that the honorarium did not impress her. She explains that men could give her fifty dollars for accompanying them to the women’s room, plus another fifty for cab fare. The comparison places the prison arrangement in the transactional economy she knows, but her eventual decision is not described as simple calculation.

Once the lawyer named his client as Tomato, he told her that the old man had long admired her from a distance and suggested that a weekly visit would be a good deed. Holly says she could not refuse because it seemed romantic. Her account therefore combines money, charity, and romantic appeal rather than reducing the visits to any one motive. She says she went every Thursday for seven months, and believes she would have continued even without payment.

Holly’s Account of Tomato

Holly describes Tomato as a darling old man who was terribly pious and prayed for her every night. She says he might have looked like a monk if not for his gold teeth. She also notes that she spoke Yiddish better than he spoke English, a detail that distinguishes their companionship from a conventional romance and helps establish the personal texture of the visits.

She says she adored him after making the visits, while explicitly denying that he had ever been her lover. Her recollection makes religious affection and regular companionship the relationship’s defining features. At the same time, the weekly payment remains part of the arrangement, preventing the story from presenting her kindness as wholly separate from the material circumstances in which she lives.

The Public Accusation

On the evening of Holly’s arrest, newspaper headlines framed her as a playgirl, actress, and alleged drug smuggler. One report said that prosecutors considered her a key figure in a narcotics ring dominated by Tomato, who was then serving his five-year sentence in Sing Sing. The account alleged that Holly posed as a relative, visited him weekly, and carried verbally coded messages from him to Oliver “Father” O’Shaughnessy, his chief lieutenant. The alleged chain of communication supposedly enabled Tomato to maintain control of a worldwide syndicate from prison.

The reports do not establish those claims as facts. The newspaper itself says the district attorney’s office would not supply details or verify the allegations. Holly, speaking to reporters after her arrest, acknowledges that she visited Tomato every week but denies that he spoke to her about drugs. She defends him as a religious, sensitive old man and expresses anger at what she sees as persecution. Her admissions about the visits thus confirm the visible circumstances that made the accusation plausible while leaving the alleged criminal purpose disputed.

Narrative Role and Consequences

The episode is disclosed in stages. Holly first recounts the visits to the narrator as a story she might have to disguise under different names; later, newspaper coverage supplies a sensational version of the same relationship. That shift in presentation changes the meaning of familiar details—weekly visits, an assumed family connection, and a friendship formed in prison—without resolving whether Holly understood any messages as criminal communications.

The imprisonment is therefore consequential less as a fully narrated prison episode than as the condition that brings Holly and Tomato together and later exposes her to public suspicion. A paid visit that Holly remembers as a romantic good deed becomes, in the newspapers’ account, an alleged conduit between a jailed syndicate leader and an accomplice outside. The conflict between those interpretations remains central: the evidence confirms the visits and the arrest, but the prosecution’s account is reported as an allegation, not established truth.