A cup bearer was the person that tasted the food and drink of the king before he ate or drank. That way, if it was poisoned, “So long, cup bearer,” but “Long live Pharaoh. This led straight to a really tight relationship, a relationship of trust between the 2 men. Regularly the king of the land would confide in the cup bearer. If you recall, Nehemiah was the cup bearer to the king of his day and had a close, private relationship with him. In a number of ways, the cup bearer was the most reliable man of the court.
If that trust was ever damaged, major implications followed. Something similar to that must have occurred, as the cupbearer to Pharaoh landed in jail—as had also the king’s baker. ( He was someone else on whom the pharaoh relied, because whatever he prepared passed into the mouth of the Egyptian ruler. ) The specifics of what had happened to cause this falling out and punishment we are never told. All we all know is that they “offended their lord” and he was “furious with his 2 officials.” Perhaps the biscuits dropped that morning, and later there were too many jalapenos in the chili, and the cupbearer did not warn Pharaoh.
It must’ve been related to the food because their roles were interrelated. But whatever it was, it made Pharaoh so indignant that he claimed, “Get out of my sight. And since God’s techniques are deep and surpassing, it occurred to be the same jail where Joseph was detained. Joseph and these 2 men may have finished up in jail for different reasons, but they found themselves in the same place, sharing similar miseries. And out of his very own unpleasant experience, Joseph was ready to minister to them.