A cupbearer was the person who tasted the wine and food of the king before he ate or drank. That way, if it was poisoned, “So long, cupbearer,” but “Long live Pharaoh!” He also would not allow poorly prepared food to be served to the pharaoh since he was responsible for watching the monarch’s diet. This led to a very close relationship, a relationship of trust between the two men. Often the king of the land would confide in the cupbearer. If you recall, Nehemiah was the cupbearer to the king of his day and had a close, personal relationship with him. In many ways, the cupbearer was the most trusted man of the court. If that trust was ever broken, serious consequences followed.
Something like that must have happened, because the cupbearer to Pharaoh landed in jail—as had also the king’s baker. (He was another person on whom the pharaoh relied, because whatever he prepared passed into the mouth of the Egyptian ruler.) The specifics of what had happened to bring about this falling out and punishment we’re never told. All we know is that they “offended their lord” and he was “furious with his two officials.” Maybe the biscuits fell that morning, and later there were too many jalapenos in the chili, and the cupbearer didn’t warn Pharaoh! It must have been related to the food because their jobs were interrelated. But whatever it was, it made Pharaoh so angry that he said, “Get out of my sight!” and had them both thrown in jail. And since God’s ways are deep and profound, it happened to be the same jail where Joseph was imprisoned.
Isn’t it remarkable how often God brings alongside us people who are going through, or have gone through, similar experiences? Isn’t it amazing, when we are hurting, God brings alongside us others who understand our pain? That is certainly true here. Joseph and these two men may have ended up in prison for different reasons, but they found themselves in the same place, sharing similar miseries. And out of his own painful experience, Joseph was able to minister to them.