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Let's say my good friend Bob is an employee at Frank's Store of Stuff You'd Never Pay Full Price For. He gets an employee discount for his purchases there. Can Bob buy stuff and then sell it to me, or buy stuff directly for me?

What about for his wife and immediate family?

Let's say that the owner is unavailable to ask if he is OK with that or not, and my one-way flight to Mars is about to leave so I can't wait until he becomes available.

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I would think that the normal assumption for an employee discount would that it would be for the personal use of the employee and not for his friends and not for him to do business with. I am supported in this by this article about the Original Employee Discount.

He quotes:

“When you come [to work] in your neighbor’s vineyard, then you may eat the grapes you desire until you are satiated, but you shall not put any in your container. When you come [to work] in the ripe grain of your neighbor, then you may pick the grain with your hand, but you may not take a sickle to your neighbor’s grain” (Deuteronomy 23:25-26).

and the Talmud Baba Metzia 87a-b to say

“Produce that still needs to ripen may not be eaten, and the employee may not take extras to enjoy later.”

Shulchan Oruch Choshen Mishpot 337 [16] does not allow the worker to take for his wife and children.  

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