It is unclear how much he actually knew. Midrash Tehilim earlier indicates that Benjamin knew that his brother was alive when Jacob was mourning for him, but doesn't explain whether he knew that he was sold. Sefer HaYashar in this week's Parsha explains that when Joseph saw Benjamin in Egypt and made a banquet with the brothers, it was during the banquet that he revealed himself and warned Benjamin about the upcoming plan to hide a silver goblet in his bags. However, Joseph doesn't tell him how he ended up in Egypt. Tzror haMor writes that after revealing himself to Benjamin, Joseph made up a story about how he was attacked by an animal, and eventually kidnapped and sold into slavery by some passing traders. However, other midrashim later on (Midrash Rabbah, Tanchuma, Aggadas Bereishis) write that when Benjamin's bags were searched and the goblet found, he rebuked the brothers using the example of Joseph's sale, thus indicating that he knew what happened.
Did Jacob know about the sale of Joseph?
It is also unclear how much he knew. Many learn that he never found out about the sale of Joseph, but there are some that learn that Joseph did tell him shortly before his death. Sefer Shemiras haLoshon writes that Jacob found out via divine inspiration and wasn't told by anyone. In any case, Rashi in Parshas Vayechi indicates that he did know because the blessings to Shimon and Levi, and the blessings to Joseph are interpreted in a way that directly relates to the sale of Joseph.
Additional interesting points:
- The Chasam Sofer learns that someone else should hold the candle during Bedikas Chametz because Menashe had a servant hold the candle while he searched the brothers' bags because it was Sabbath
- One of the reasons why it was easy for the Hashmonaim to become kings after their victory was because during the Second Temple era, the position of the High Priest was partly political since the empires that ruled Israel at that time treated the High Priest as a representative of the Jewish People (as seen from the story of Alexander the Great and Shimon haTzadik)
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