We find this story elaborated upon in Legends of the Jews by Ginzberg.
The brothers hadn't even cleared the city gates when Joseph, eager to spring his trap but also wary of letting them get too far, sent his steward, Manasseh, after them. His mission? To accuse them of theft and bring them back. Joseph, ever the strategist, hoped the proximity to the city would make them more compliant.
Manasseh, following orders, caught up with them. "The silver cup is missing!" he declared, accusing them of theft. The brothers, indignant and sure of their innocence, responded with bravado: "With whomsoever of thy servants the cup be found, let him die, and we also will be my lord's bondmen." A harsh sentence, but they were confident.
Manasseh, playing his part perfectly, softened the blow, or so it seemed. "He with whom the cup is found shall be the bondman, and the rest shall be blameless." He then proceeded to search their sacks, starting with Reuben, the eldest, to avoid suspicion, and ending with Benjamin, the youngest. And, of course, the cup was found in Benjamin's sack.
Imagine the scene. The shock, the outrage. "O thou thief and son of a thief!" the brothers shouted at Benjamin, according to Ginzberg's retelling. "Thy mother brought shame upon our father by her thievery, and now thou bringest shame upon us." Benjamin, bewildered, could only retort, "Is this matter as evil as the matter of the kid of the goats—as the deed of the brethren that sold their own brother into slavery?" Ouch.
In their fury and vexation, the brothers rent their clothes – a powerful symbol of grief and despair. Midrash Rabbah connects this act to their past sin, noting that just as they caused Jacob to tear his clothes in mourning for Joseph, they now tear their own. And, in a fascinating twist, it also foreshadows Mordecai, a descendant of Benjamin, tearing his clothes on account of his brethren, the people of Israel, in the story of Purim.
But the consequences didn’t end there. Because Manasseh, Joseph's steward, caused them such grief, the tribe of Manasseh's territory was "torn" in two, with half on one side of the Jordan and half on the other. And Joseph himself, for his harsh treatment of his brothers, was punished through his descendant Joshua, who tore his clothes in despair after the defeat at Ai.
Convicted, the brothers had no choice but to return to the city. As they walked, they continued to berate Benjamin, "O thou thief and son of a thief, thou hast brought the same shame upon us that thy mother brought upon our father." Yet, Benjamin bore their abuse in silence, and for his humility, God promised that His Shekinah (Divine Presence) would "dwell between his shoulders," and called him "the beloved of the Lord."
Back in the city, they were brought before Joseph. They fell to the earth before him, fulfilling his childhood dream of dominance. But Judah, simmering with rage, warned his brothers, "Verily, this man hath forced me to come back hither only that I should destroy the city on this day."
Joseph, through an interpreter, accused them of stealing the cup to divine the whereabouts of their lost brother. Judah, ever the eloquent spokesman, protested their innocence, but acknowledged that "God hath found out the iniquity of thy servants." He even suggests that their collective sin, the selling of Joseph, was the reason they were all caught together.
Joseph then delivered what seemed like a final blow: only Benjamin would remain as his slave. "Go hence, and tell your father, 'The rope follows after the water bucket.'" In other words, bad luck comes in threes.
But the story isn't over. Judah, unable to bear the thought of his father's grief and Benjamin's enslavement, steps forward, ready to fight. As we read in Legends of the Jews, "Now it is all over with peace!" he cried, preparing to use force to rescue Benjamin.
What happens next? Well, that's a story for another time. But the stage is set for a powerful confrontation, a moment of truth that will reveal the true nature of these brothers and the depths of Joseph's plan. It makes you wonder: how far is too far when seeking justice or reconciliation? And what price are we willing to pay for the mistakes of our past?
They were not yet far beyond the city gates, when Joseph dispatched Manasseh, the steward of his house, to follow after them, and look for the silver cup that he had concealed in Benjamin's sack. He knew his brethren well, he did not venture to let them get too far from the city before he should attempt to force their return. He hoped that the nearness of the city would intimidate them and make them heed his commands. Manasseh therefore received the order to bring them to a halt, by mild speech if he could, or by rough speech if he must, and carry them back to the city. He acted according to his instructions. When the brethren heard the accusation of theft , they said: "With whomsoever of thy servants the cup be found, let him die, and we also will be my lord's bondmen." And Manasseh said, "As you say, so were it proper to do, for if ten persons are charged with theft, and the stolen object is found with one of them, all are held responsible. But I will not be so hard. He with whom the cup is found shall be the bondman, and the rest shall be blameless." He searched all the sacks, and in order not to excite the suspicion that he knew where the cup was, he began at Reuben, the eldest, and left off at Benjamin, the youngest, and the cup was found in Benjamin's sack. In a rage, his brethren shouted at Benjamin, "O thou thief and son of a thief! Thy mother brought shame upon our father by her thievery, and now thou bringest shame upon us." But he replied, "Is this matter as evil as the matter of the kid of the goats—as the deed of the brethren that sold their own brother into slavery?" In their fury and vexation, the brethren rent their clothes. God paid them in their own coin. They had caused Jacob to tear his clothes in his grief over Joseph, and now they were made to do the same on account of their own troubles. And as they rent their clothes for the sake of their brother Benjamin, so Mordecai, the descendant of Benjamin, was destined to rend his on account of his brethren, the people of Israel. But because mortification was inflicted upon the brethren through Manasseh, the steward of Joseph, the allotment of territory given to the tribe of Manasseh was "torn" in two, one-half of the tribe had to live on one side of the Jordan, the other half on the other side. And Joseph, who had not shrunk from vexing his brethren so bitterly that they rent their clothes in their abasement, was punished, in that his descendant Joshua was driven to such despair after the defeat of Ai that he, too, rent his clothes. Convicted of theft beyond the peradventure of a doubt, the brethren of Joseph had no choice but to comply with the steward's command and return to the city. They accompanied him without delay. Each of them loaded his ass himself, raising the burden with one hand from the ground to the back of the beast, and then they retraced their steps cityward, and as they walked, they rapped Benjamin roughly on the shoulder, saying, "O thou thief and son of a thief, thou hast brought the same shame upon us that thy mother brought upon our father." Benjamin bore the blows and the abusive words in patient silence, and he was rewarded for his humility. For submitting to the blows upon his shoulder, God appointed that His Shekinah should "dwell between his shoulders," and He also called him "the beloved of the Lord." Joseph's brethren returned to the city without fear. Though it was a great metropolis, in their eyes it appeared but as a hamlet of ten persons, which they could wipe out with a turn of the hand. They were led into the presence of Joseph, who, contrary to his usual habit, was not holding a session of the court in the forum on that day. He remained at home, that his brethren might not be exposed to shame in public. They fell to the earth before him, and thus came true his dream of the eleven stars that made obeisance to him. But even while paying homage to Joseph, Judah was boiling inwardly with suppressed rage, and he said to his brethren, "Verily, this man hath forced me to come back hither only that I should destroy the city on this day." Guarded by his valiant men on the right and on the left, Joseph addressed his brethren, snarling, "What deed is this that ye have done, to steal away my cup? I know well, ye took it in order to discover with its help the whereabouts of your brother that hath disappeared." Judah was spokesman, and he replied: "What shall we say unto my lord concerning the first money that he found in the mouth of our sacks? What shall we speak concerning the second money that also was in our sacks? And how shall we clear ourselves concerning the cup? We cannot acknowledge ourselves guilty, for we know ourselves to be innocent in all these matters. Yet we cannot avow ourselves innocent, because God hath found out the iniquity of thy servants, like a creditor that goes about and tries to collect a debt owing to him. Two brothers take care not to enter a house of mirth and festivity together, that they be not exposed to the evil eye, but we all were caught together in one place, by reason of the sin which we committed in company." Joseph: "But if your punishment is for selling Joseph, why should this brother of yours suffer, the youngest, he that had no part in your crime. Judah: "A thief and his companions are taken together." Joseph: "If you could prevail upon yourselves to report to your father concerning a brother that had not stolen, and had brought no manner of shame upon you, that a wild beast had torn him, you will easily persuade yourselves to say it concerning a brother that hath stolen, and hath brought shame upon you. Go hence, and tell your father, 'The rope follows after the water bucket.' But," continued Joseph, shaking his purple mantle, "God forbid that I should accuse you all of theft. Only the youth that stole the cup in order to divine his brother's whereabouts shall remain with me as my bondman; but as for you, get you up in peace unto your father." The holy spirit called out, "Great peace have they which love thy law!" The brethren all consented to yield Benjamin to the ruler of Egypt, only Judah demurred, and he cried out, "Now it is all over with peace!" and he prepared to use force, if need be, to rescue Benjamin from slavery.