“And Yosef commanded that the monies of each [brother] should be returned to his sack” (B’reishis 42:25). There has been much discussion regarding why Yosef treated his brothers so harshly (see Ramban on 42:9 and Kli Yakar on 42:7, see also pg. 2 of http://www.aishdas.org/ta/5767/miketz.pdf), but returning the money they had brought to buy food with doesn’t seem to fit this pattern. I would therefore like to discuss several approaches as to why Yosef instructed his staff to put the money back into his brothers’ bags without telling them.
The Brisker Rav is quoted as having said that Yosef did this to make sure that his brothers would return to Egypt. He had made it a very unpleasant experience for them, and was afraid they would make do with whatever they had (some food was available in Canaan, even if grain wasn’t, see 43:11) to avoid having to deal with that ogre of a ruler in Egypt. Knowing that they would never keep money that didn’t belong to them and would therefore have to come back to Egypt to return it, Yosef put the money back into their bags.
Rav Yitzchok Sorotzkin, sh’lita (Rinas Yitzchok I) asks three questions on this approach, leaving them all unanswered. First he asks how Yosef could be so sure that they would come back to return the money if they weren’t obligated to do so (see Rambam’s Hilchos G’zaila va’Aveida 11:3). However, since they knew there was a distinct possibility that the money was purposely put there to make them look bad (see Rashi on 42:28 and Radak on 42:35), they would have been required to return it (as Rambam himself says there). Secondly, he asks why, if they had to return the money, didn’t they do so right away when they lodged, when Levi found his (see Rashi on 42:27). However, since they had to bring food back to their families, returning the money to Egypt right away was not more important than feeding the hungry ones back home first and then returning the money later. The fact that when they returned (43:21) they said that all of them had found their money in their sacks when they lodged (and not just one of them) shows that delaying returning the money so that they can feed their families as soon as possible was acceptable. [Otherwise why would they make themselves look worse by admitting that they weren’t that far from Egypt when they first realized that their monies were in their bags? Obviously, the need to return the money is not contradicted by not bringing it back immediately after it was discovered.] His third question is rather straightforward; when they returned, it wasn’t to return the money, but because they needed more food (43:2). Bringing the money back was just an afterthought (see 43:12), not the main reason they went. However, these were Yaakov’s words, not his sons’ words. They couldn’t go back to Egypt without Binyamin (see 42:20 and 43:3-5), and until Yaakov allowed them to bring Binyamin, they couldn’t go just to return the money. And Yaakov, who didn’t trust them with Binyamin (nor did he trust that the money wasn’t really stolen from the Egyptians, see B’reishis Rabbah 91:9, so he couldn’t trust them to return it), only let him go with them because otherwise they would all starve (see 43:8). Therefore, the impetus for Yaakov allowing them to bring Binyamin, which was a prerequisite for returning, does not negate the possibility that Yosef wanted to give them an added incentive to return in case they could survive without buying more food. He couldn’t know that Yaakov would only allow Binyamin to go if they would otherwise starve to death (or that Yaakov was even still alive, or if the brothers would value Yaakov’s wishes regarding Binyamin after having ignored their father’s wishes when they sold him to Egypt). All he knew (based on knowing how careful his family was with other people’s money) was that even if the shortage of food wasn’t enough to force them to return, all things being equal, having to return money that didn’t belong to them would make them want to return.
In a similar vein, Abarbanel suggests that Yosef wanted to make sure that the family would have enough money to come back to buy more food, so he put theirs back in their bags. Although this has nothing to do with the importance of treating other people’s money with reverence, it does speak to Yosef’s concern that they return. And with food being so scarce, it would not be far-fetched to have been concerned that even a family as wealthy as his might have had to use all of their resources to purchase food, and may not have enough to buy more. Nor was it unreasonable to be concerned that others had pillaged their things because of the shortage. Therefore, Yosef gave their money back in case they needed it after the food they had just bought was consumed.
When Shimon was taken from them and put in prison, the brothers acknowledged their guilt for having ignored Yosef’s pleas for mercy (42:21). Rashbam is among the commentators who point out that the brothers recognized that they were being punished “measure for measure,” something that was likely Yosef’s plan to help them understand what they had done wrong (see Abarbanel and Kli Yakar). When it came to finding the money in their sacks, though, they wondered how this was also “measure for measure” (see Rashbam and Chizkuni on 42:28). S’fornu (ibid) says they thought the money was purposely put there to frame them as thieves in order to make them slaves, which they recognized as being “measure for measure” for having sold Yosef into slavery, but they were puzzled because they thought selling Yosef into slavery was an act of mercy, since he really deserved to be executed for trying to have them excluded from G-d’s “treasured nation” (see http://www.aishdas.org/ta/5767/vayeishev.pdf). They therefore wondered how this qualified as “measure for measure” if the intent of the Viceroy was malicious (enslaving them when they did nothing wrong) while theirs was an act of generosity. It is therefore possible that Yosef purposely did something (putting their money back in their bags) that would force them to try to figure out how it qualified as “measure for measure” in order to get them to reexamine every detail of what they had done to him, in the hope that by doing so they would finally realize the extent of what they had done wrong.
Radak (44:1, see also 42:27) understands Yosef’s intentions throughout to be to cause them stress without doing any real damage. Abarbanel has a similar approach, adding that just as what the brothers did to him caused him stress (being sold as a slave and going to prison) but ended up being a good thing (as he became a ruler in Egypt and was able to support everyone, including his family, during a severe famine), Yosef tried to get them to understand what they had done wrong by causing them “measure for measure” stress without doing any real harm. Had they figured out that he was Yosef before everything played itself out (including, and especially, before he forced them to bring Binyamin to Egypt so he could verify that they would fight for Rachel’s younger son even though they had treated her older son so poorly), the plan would have been foiled, the brothers would likely not have repented, and the chasm between Yosef and his brothers would have grown even wider. It is therefore possible that Yosef put the money back into his brothers’ sacks not only to get them to try to figure out what they had done wrong to deserve this, but to further increase their stress level so that they would be too distracted to figure out he was Yosef. Even when “the man who oversaw Yosef’s house” told them that the money in their sacks was not considered stolen (43:23), Yosef had their donkeys confiscated (43:18) in order to make them think that they were going to be kept as slaves (see R’ Chaim Paltiel and Chizkuni), making sure that their stress levels were kept high. By preventing them from having any peace of mind, the brothers were unable to put all the pieces together, allowing Yosef’s plan to run its course.