Why is there a double expression, "v'Lo Zachar... va'Yishkachehu"?
Rashi and Targum Yonasan: He did not remember him on the day that he was released; and he forgot him for a long time afterwards (until Hashem performed miracles on behalf of Yosef, and he was needed - Rashbam).
Da'as Zekenim (to 40:14): The butler forgot to mention Yosef to Pharaoh, whether personally or via a Shali'ach. See above, 40:14:152:1 .
Moshav Zekenim: "V'Lo Zachar" - The butler intentionally did not mention Yosef to Pharaoh, until "va'Yishkachehu" - Pharaoh forgot why he had been angry at the butler.
Oznayim la'Torah (based on Bereishis Rabah): "Va'Yishkachehu" implies that he forgot 'against his will.' 1 The butler actually made knots to remind himself to inform Pharaoh about Yosef, but an angel made him forget to do so until Pharaoh dreamt - so that Yosef should be brought before Pharaoh to interpret his dream. 2
Riva and Hadar Zekenim: And if the Torah advocates on behalf of Resha'im (by implying that in this he was a Shogeg), how much more so will it advocate on behalf of Tzadikim!
Oznayim la'Torah: Had Pharaoh released Yosef now, he would not have subsequently known where he was. In fact, he would probably have returned home to his father.
What did Yosef do to deserve remaining in jail two more years (as the next Pasuk (41:1) tells us)?
Rashi: He placed his faith in an Egyptian (Tehilim 40:5), whom the Pasuk (Yeshayah 30:7) refers to as arrogant. 1
Targum Yonasan: He placed his faith in a human being, and not in Hashem. 2
Midrash Rabah (89:3): Two years were added due to his two requests of the butler to remember him.
Targum Yerushalmi: As the Pasuk says, "Arur ha'Gever Asher Yivtach ba'Adam... " (Yirmeyahu 17:5). Refer also to 42:9:4:1**.
QUESTIONS ON RASHI
Rashi writes: "Because Yosef placed in trust in [the butler] remembering him, he had to be in jail for another two years." How do we know that this was the cause?
Gur Aryeh: Chapter 41 (the beginning of Parshas Miketz) will make it clear that the butler failed to mention Yosef until two years had passed. Our verse therefore seems to be unnecessary. It tells us that Hashem brought it about that the butler would not remember Yosef for these two years, because Yosef had placed his trust upon him.
Rashi writes: "... In jail for another two years." Why specifically two years?
Gur Aryeh #1: Yosef used two expressions in his request - "mention me" and "take me out" (40:14) - and one year was decreed upon him for each request.
Gur Aryeh #2: Yosef still hoped for the butler to remember him for one full year; but once a year passed he had certainly forgotten. 1 Yosef was punished with an additional year, corresponding to the year that he had placed his reliance upon the butler.
Gur Aryeh: See Berachos 58b. A Gematriya hint to this, is that the word "va'Yishkachehu" equals "Shanah" (355); meaning that once Hashem ensured that the butler forgot for one year, he would no longer remember on his own. Alternatively, the words "Im Zechartani" (40:14) (plus two for the two words) equal 730, corresponding to the 730 days in two solar years. That is why his release came after "two years of days" (41:1).
