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Answer:We will divide this question into different possible models of business interaction and analyze each one according to its halachic logic and sources. Was Shimon acting as a shaliach (agent), for free or, more likely, for some form of profit, on behalf of you or Levi? Was Shimon acting as a business, which paid Levi for oil and its delivery to destinations of his choice, and received money from you and others for assuring the same?
If Shimon was a shaliach, you have a natural obligation toward Levi for giving you his oil at your request (through the agency of Shimon), and the question is whether anything exempts you. The mishna (Bava Metzia 98b) says that if Gad decides to borrow an object from Asher and tells Asher to send it to him by means of Yisachar, then once it enters Yisachar’s hands, Gad assumes full responsibility for it. If Gad did not instruct him whom to send it with, then Gad is not responsible for it until it enters his possession. The poskim (see Beit Yosef, Choshen Mishpat 121) apply this gemara to sending payment for a loan through a courier. Similarly, in this case, if Shimon served as your agent to bring your money to Levi and instruct him to deliver oil to you, then if Shimon stole the money, he stole it from you, and there is nothing to exempt you from owing Levi. However, if Shimon served as Levi’s agent to arrange for his sales and collect his charges, then once Shimon received the money, it is as if you had paid Levi, and the fact that Levi’s representative pocketed money coming to him is Levi’s problem.
Let us consider the possibility that Shimon is a business entity, serving as a middleman. Then, he would have two business relationships: between you and him and between Levi and him. If so, he got what he wanted from you (the money) and provided you with the service you deserved (a delivery of oil). Shimon’s lacking was in his relationship with Levi. He received what he requested from Shimon (oil for his customer) but did not keep his part of the deal with Levi (paying him). It follows then that he stole from Levi, not from you, and Levi has to deal with that.
But don’t you owe Levi because you benefitted from his oil? Consider the following case in the gemara (Bava Metzia 76a). If Dan had Naftali work in Zevulun’s field under Dan’s responsibility, Dan has to pay Naftali at the rate they discussed, and Zevulun has to pay Dan for the benefit Dan brought him (which might be less than what Dan promised Naftali). Zevulun does not have a direct obligation to pay Naftali even though Naftali did the work in his field. Although if Dan runs away, Zevulun will have to pay Naftali for his benefit, that is because there is no reason for him to benefit for free while Naftali remains uncompensated. In contrast, in your case, you already paid for the benefit you received, and Levi has to go after the person who was responsible for his payment.
We cannot give a ruling without hearing both sides, but we suggest to you the following. Because you might not be able to determine which of the models applies to your case and because it seems mentchlach, we recommend that you offer Levi that, if the money is not recovered, you will pay him a sizable minority of the money he has lost.
Bemare Habazak - Rabbis Questions (657)
Various Rabbis
43 - Shemoneh Esrei With the Chazan?
44 - Making Up the Money Absconded by a Middleman
45 - Wearing a Reflective Armband on Shabbat Without an Eiruv
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Bemare Habazak - Rabbis Questions Ask the Rabbi: Having a Non-Jew Build a Sukka and Assemble Arba’a Minim
Rabbis in Midrash
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