בעוד שלשת ימים ישא פרעה את ראשך והשיבך על כנך
“In another three days, Pharaoh will count you and will restore you to your post” (Bereishis 40:13)
The Gemara in Berachos (55b) teaches that the meaning of a dream is determined by the interpretation given by those who hear it. The Brisker Rav asks an interesting question: Why didn’t Yosef, upon hearing the dream of the cupbearer, “interpret” it to mean that his death was imminent, which would then come to pass, just as it occurred with the baker? In other words, if it was in Yosef’s hands to cause a wicked non-Jew to die, why did he save him by giving an alternative interpretation?
The Brisker Rav answers that the baker decided to relate his dream to Yosef only after he saw that Yosef offered a positive interpretation of the cupbearer’s dream (Bereishis 40:16). Thus, if Yosef told the cupbearer that his dream forebode imminent death, the baker would have feared for his own life and kept his dream to himself, thereby depriving Yosef of the opportunity to bring about his death by interpreting his dream to mean that he would die.
In other words, regardless of how Yosef would interpret the dream of the cupbearer, one of his cellmates would die and one would live. The difference was that if he “killed” the cupbearer, the baker would live and eventually be freed from prison, but he would have felt no sense of gratitude toward Yosef. Therefore, Yosef concluded that it would be preferable to give a positive interpretation of the cupbearer’s dream. This would leave the cupbearer indebted to him for his freedom, which he hoped would help bring about his release from prison, while still allowing him to “kill” the baker. (R’ Ozer Alport, Parsha Potpourri)