How could Yosef be so ready to go to his brothers, knowing how much they hated him?
Seeing as the brothers took it in turn to serve their father (Rashi to 37:29), why was it necessary to send Yosef to make enquiries?
Oznayim la'Torah: Because knowing that they were lax in looking after the sheep, 1 the only one Yaakov could trust regarding news of the sheep 2 was Yosef.
Refer to 37:12:1:1 and 37:12:1.1:3.
Oznayim la'Torah: And he only added "Es Shelom Achecha" by the way.
What are the ramifications of Yosef's reply "Hineini!"?
Oznayim la'Torah: It can be compared to the "Hineini" of Moshe at the Burning Bush, which the Midrash interprets as "l'Malchus veli'Kehunah.' Here too, Yosef unknowingly declared 'Hineini l'Malchus!' - since he became the viceroy of Egypt, and 'Hineini li'Kehunah!' since he was given the Bechorah. 1
Malbim: Refer to 37:13:151:4.
See Oznayim la'Torah
How could Yaakov send Yosef to his brothers, knowing how much they hated him?
Moshav Zekenim #1 (to 37:14), Rosh (to 37:15), Hadar Zekenim: Yaakov thought that it is a Safek if the brothers will harm him, but if the brothers delay in Shechem, Nochrim will definitely kill them 1 to avenge the destruction of Shechem. It is better to tell the brothers to return, even though there is a risk to Yosef.
Moshav Zekenim #2 and Rosh: The brothers would believe only Yosef - if their father sent his favorite son (surely he was adamant that they leave).
Hashem caused Yaakov to do so. Refer to 37:14:2:1 and the note there.
Malbim: Yaakov asked Yosef if he wants to go (Refer to 37:13:152:2), and inferred from his answer that Yosef knows that they do not hate him.
Ohr ha'Chayim (to 37:14): Yaakov did not think that the brothers hate Yosef so much that it is a clear danger, for which one may not rely on the guarantee that a Shali'ach Mitzvah is not harmed. What happened to Yosef - he was sold, for the sake of raising him [to kingship] - is not called harm.
Ha'amek Davar: Yaakov relied on Yosef's merits to protect him from evil people. 2
Based on the principle "Ein Safek Motzi mi'Yedei Vaday.'
Harchev Davar: The Zohar says that Reuven said to cast him into a pit of snakes. He was not concerned lest they kill him, due to Yosef's merit. However, man's choice is above Hashgachah; we find that Koresh was not concerned lest the lions eat Daniel, but he was concerned lest people harm him (Daniel 6:18). Clearly, Hashem can save also from people, but this needs greater merit - one who is also good to people. Yaakov estimated that Yosef, who was an amazing Ba'al Chesed (like we find later - refer to 43:5:151:1) and loved his brothers, even though they hated him, there is need to fear for him.
Why did he say "Lechah v'Eshlachacha"?
Ohr ha'Chayim: If you are concerned for their hatred, I will accompany you and send you on a Mitzvah; people going to do a Mitzvah are not harmed (Pesachim 8a).
Malbim: The Hei at the end of Lechah shows that it is not absolute. 'If you want to go, I will send you.'
Why does it say "ha'Lo"?
Ha'amek Davar: Yaakov sent Yosef because he heard that they are grazing in Shechem, which is dangerous due to the episode with Dinah, like the Rashbam says, and he was fretful to know about them.
QUESTIONS ON RASHI
Rashi writes: "Hineni - an expression of humility and alacrity." Perhaps it was merely a response [indicating that he was present (e.g. Shemos 3:4)]?
Gur Aryeh: Yaakov had already begun a conversation with Yosef. ("Are your brothers not grazing in Shechem, etc.") 1 Yaakov already knew that Yosef was present. Rather, here, the word 'Hineni' indicates Yosef's willingness to do Yaakov's bidding.
Hineni as a simple response always comes at the beginning of a conversation. Here, this was not the case. (EK)
