Dov once stole $700 from someone and later felt terribly guilty. “I’d like to return the money but don’t know how,” Dov confided to his friend Aharon.
“Just give back the money,” said Aharon.
“I’m embarrassed to face him,” replied Dov. “Perhaps I can just leave the money at his house.”
“How is he going to know it’s from you?” objected Aharon.
Dov deliberated for a number of days and finally decided to ask Rabbi Dayan. “I’m ashamed to admit,” Dov said when he finally found himself before the rabbi, “but I stole money from someone and would now like to return the amount without having to face him. Is that possible?”
“Rav Moshe Feinstein, zt”l, addresses this question in his responsa [Igros Moshe, Choshen Mishpat 1:88],” replied Rabbi Dayan. “He said it depends on the circumstances of the theft. If the victim never realized anything was stolen from him, the thief need not tell him he is returning the money. He can just leave it discreetly at his house or mail it to him without revealing his identity. However, he must ensure the envelope is received – perhaps by using registered mail.” [Choshen Mishpat 355:1]
“Even if the victim knew money was stolen from him, revealing one’s identity is not necessary as long as he knows the money was returned,” added Rabbi Dayan. “If he knows who stole from him, however, the thief probably must tell him he is returning the money since otherwise he might suspect that someone else sent him the money.”
“In addition, Rav Moshe writes that if the victim suffered from the theft, the thief must request forgiveness,” concluded Rabbi Dayan. “The Gemara [Yoma 86b] states that if a person sinned against his fellow man, he shouldn’t hide his sin. The Rambam [Hilchos Teshuvah 2:5] indicates that part of regretting one’s sins is confessing publicly, which requires revealing one’s identity. Rashi writes that confessing publicly leads to others encouraging the victim to forgive him.
“Based on this comment by Rashi, Rav Moshe concludes that a person can perhaps write an anonymous letter of apology stating that he is returning what he stole and requesting forgiveness.”