Who was the "Ish" who found him wandering around in the field?
Rashi and Targum Yonasan: It was the angel Gavriel. 1
Hadar Zekenim and Rosh: "Ish" is the Gematriya of Refa'el.
Who is referred to as "ha'Ish Gavriel" (Daniel 9:21). See also Ba'al ha'Turim.
Rashi says that the "Ish" was an angel. Why did Hashem send an angel to lead him to his brothers? Why would it not have sufficed for the Midyanim to have found him and sold him to Potifar directly?
Oznayim la'Torah: The time had come for first Yosef, 1 and then Yisrael, to go down to Egypt, and lest anyone think for one moment that the events that now unfolded were natural, Hashem first put it into the head of Yaakov to send his favorite son to his brothers, whom he knew, hated him, and then an angel to assist him in finding them, to make it abundantly clear that it was all Min ha'Shamayim (since it was all part of His Divine Plan).
Oznayim la'Torah: Had the Midyanim found Yosef and sold him to Potifar directly, people would have wondered, when his father and brothers followed, what Yisrael had done wrong to be subjugated and enslaved more than any other nation. 2
Oznayim la'Torah: In order to prevent Yaakov from going to Galus in chains.
Oznayim la'Torah: Just as Moshe would later wonder - Refer to Shemos 2:14:3:2. Following the episode with the sale of Yosef, the question was automatically answered - just as Moshe concluded there.
What is the significance of the phrase that Yosef "was wandering around... "?
Ramban #1 and Rashbam: This teaches us Yosef''s Tzidkus - despite his brother's hatred, he refused to return to his father without having fulfilled his mission.
Ramban #2: Moreover, it teaches us that when Hashem issues a decree, nothing can prevent its fulfillment. Having decreed that the Galus was due to begin, 1 when Yosef could not find his brothers (who were destined to set the Galus in motion), Hashem sent an angelic guide to lead him to them.
Da'as Zekenim: The word "To'eh," and also "va'Echar Ad Atah" (Bereishis 32:5) hints at the three Galuyos - 400 years of Galus Mitzrayim ('Tav'), 70 years of Galus Bavel ('Ayin') and Galus Edom, which will end after the year 5000 ('Hei'). 2
Refer to 37:14:2:1**.
I do not know the source that Galus Edom was destined to end then (PF). Chazal generally discussed four Galuyos after Matan Torah - Bavel, Madai, Yavan and Edom (Bereishis Rabah 2:4).
Why does it say "ba'Sadeh" (which implies a known field)?
Malbim: This is the field that Yaakov bought from Bnei Chamor. He thought to find them there.
QUESTIONS ON RASHI
Rashi writes: "'A man (Ish) found him' - This was Gavriel." What in our verse indicates that this "Ish" was an angel?
Mizrachi: Yosef does not ask, 'Do you know where they are?' but rather, "Please tell me where they are!" (37:16). It must have been an angel, who would be expected to know this information.
Gur Aryeh: Why does the Torah relate this encounter with the "Ish" at all? Hashem sent a Mal'ach to ensure that Yosef would encounter his brothers. Otherwise, upon failing to find them in Shechem, he would have returned home!
Rashi writes: "'A man (Ish) found him' - This was Gavriel." How do we know it was specifically Gavriel?
Gur Aryeh #1: He is referred to elsewhere as "ha'Ish Gavriel" (Daniel 9:21). Also, the name Gavriel is based on the word 'Gever,' which is synonymous with 'Ish.'
Gur Aryeh #2: The term "Ish" appears again in our Pasuk ("the Ish asked," rather than a pronoun 'he asked'). It must refer to the "Ish" we know from elsewhere, i.e. the angel Gavriel.
Rashi writes that the "Ish" was an angel. (Hashem sent him to lead Yosef to his brothers.) If so, why did he ask him what he was looking for?
Oznayim la'Torah #1: So that he should not realize that he was an angel.
Oznayim la'Torah #2: In order to enter into a conversation with him.
