What did Yosef mean when he said "Ki Im Zechartani Itcha"?
Rashi, Seforno and Rashbam: Yosef was convinced of his prediction that Pharaoh would favor the chief butler to such an extent that, with a good word from him, Pharaoh would set him free. 1
Ramban: 'If, when Pharaoh is good to you (and takes you out of prison), you will remember me then you will do me a great kindness and truth by mentioning me to Pharaoh'.
See Sifsei Chachamim.
What are the connotations of the word "Na"?
Rashi: "Na'" is a Lashon of request (Please).
Ramban: "Na" is either a Lashon of request, or it means now. 1
What is the significance of the word "Itcha"?
Ramban #1: That, with a good word from the butler, Pharaoh will take Yosef out 'with him', so to speak.
Ramban #2: That the butler should remember him in his heart as if he was with him.
Ramban #3: Should he remember him for the good, he should tell Pharaoh about the young man who served him in jail, and ask him for permission to leave jail and continue to serve him. 1
Wat did Yosef mean when he said "v'Hizkartani El Pharaoh... "?
Ramban #1: Refer to 40:14:2:3.
Ramban #2 and Seforno: He asked the butler just to remind Pharaoh about him, since he knew him from the time that he worked for Potifar, his officer, and he would certainly set him free.
Why didn't Yosef ask the butler to mention him to Pharaoh right away?
Moshav Zekenim citing R. Aharon: It is not honorable to be mentioned via one who was caught. Only later, when Pharaoh does good to you.... 1
Perhaps one can elaborate (with tongue in cheek) by citing the Gemara in Bava Metzi'a, 8a 'Migu d'Zachu l'Nafsheih Zachi Nami l'Chavreih' (Someone who is acquiring for oneself can also acquire for someone else at the same time) - which is what Yosef was really asking of the chief butler. (EC)
Why did Yosef say both Zechartani and v'Hizkartani?
Da'as Zekenim and Hadar Zekenim: Zechartani - you yourself [mention me]. V'Hizkartani - through a Shali'ach. 1
This was excessive Hishtadlus, and he was punished for it (refer to 40:23:2:1*). Had he properly relied on Hashem, one expression would suffice.
Da'as Zekenim: This is why it says (verse 23) that he did not remember him (that he himself should mention him), and he forgot [to mention him through a Shali'ach].