Then he commanded the overseer of his house, saying, "Fill the men's sacks with food, as much as they can carry, and put each man's money into the mouth of his sack. And my goblet, the silver goblet, put into the mouth of the sack of the youngest, and his purchase money." And he did according to Joseph's word, which he had spoken.
Breisheit 44:1-2

As seen before Yosef had showed closeness and camaraderie.
And he had portions brought to them from before him, and Benjamin's portion was five times as large as the portions of any of them, and they drank and became intoxicated with him.
Breisheit 43:34
How in one verse can Yosef sit, eat and drink with his brothers, then in the next verses turn around and seemingly set in motion a plot to have his brothers arrested.  Was his external actions truly reflective of what he felt in his heart? The Or HaChaim HaKadosh says that we have to look deeper to understand these issues.

Perhaps this suggest 3 things.
  1. In order to cleanse them of the sin of stealing, when they kidnapped him, he created suspicion about them so that there would be embarrassment about the sin of stealing Yosef and then they would be admonished of that sin.
  2. He also wanted to see if they were prepared to put up their own lives to save Binyamin. Then Yosef would be able to see how strong the trait of brotherhood was in the family, and also this would serve to cleanse them of their sin towards Yosef.
  3. He wanted to offer a hint about the sin they perpetrated on Yosef. Then they would begin to reflect on their actions and feel like maybe their is someone in this house that is familiar with their actions. Thus we saw earlier how Yosef tried to provide clues to them that he knew certain details about him, when he sat them "They sat before him, the firstborn according to his age, and the youngest according to his youth, and the men looked at each other in astonishment." (Breisheit 43:33).

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