From notes taken on a shiur by Rabbi Sitorsky - Kislev 5771...
Hanukah is in Parshat Vayeshev. ...the Shlah Hakadosh tells us that golus Yavan occurred because of the sin of the selling of Yosef Hatzadik, which automatically connects this parshah to Hanukah because it is the Shabbat that we read about Mechirat Yosef. Because of Mechirat Yosef (the sale of Yosef), there was a Greek exile and because there was a Greek exile, there was a geulah from Greece which was Hanukah. Hanukah is the geulah from the Greek exile, so Hanukah is the holiday to rectify the selling of Yosef. The sin of Mechirat Yosef was a blemish in the unity of Am Yisrael and a blemish in the area of speech. There was an aspect of lashon hara involved. Yosef reported on his brothers. Yosef Hatzadik is punished. Meforshim say the ten years of incarceration is one year for each brother that he spoke against and the other two years for lack of faith in Hashem, according to Rashi.
The Shlah Kakadosh tells us that Yosef is Hanukah. Avraham is Pesach, Yitzchak is Shavuot and Ya'aqov is Sukkot, so Yosef is Hanukah.
Hanukah is the holiday that brings near the Jews who are far away from Yiddishkeit. It affects those neshamas that no other holiday affects, including Shabbat. The most unaffiliated Jew, even if he doesn't keep Shabbat, will celebrate Hanukah. It's for those who are outside...this is our generation.
Yosef Hatzadik brings near those who were far away. Hanukah is the holiday of kiruv. Those who don't have a tikun any other time of the year, get a tikun on Hanukah.
Yosef is a hidden tzadik. He's misunderstood; not accepted. Hanukah, too, was not accepted at first. What would we be today without Hanukah? What would we be today without Yosef Hatzadik?
Yosef and Binyamin HAVE to be united.
Yosef is the rival of Eisav.
Eisav was killed on Hanukah. (Ya'aqov was buried on Hanukah.) [Eisav has his 'holiday' at Hanukah time.]
Binyamin is the rival of Yishmael.
Hanukah is the tikun for pegam habrit. It prepares us for Shovavim. The story of Yehudah and Tamar is about the blemish that would prevent Mashiach and the repair for that blemish which results in the birth of Peretz, ancestor of Mashiach.
Hanukah is not complete until Yosef and Binyamin are joined. Hanukah is the fusion of Yosef and Binyamin. Hanukah is the holiday to overpower Eisav joining with Yishmael.
Yishmael is the fifth exile. Hanukah is the fifth holiday and we drink five cups on Pesach, the fifth is the cup of redemption. These five cups appear in the parshah. "Cup" is mentioned five times. Four in the story and once again at the end of the parshah. Hanukah is the fifth cup. Hanukah is the light of Melech Hamashiach. The light of the fifth geulah after the exile of Yishmael. Corresponds to the five levels of the neshamah. Yechidah, the highest level corresponding to the fifth (which also corresponds to Neilah of Yom Kippur).
Yishmael has their mosque on the very place of the Beit Hamikdash where the miracle of Hanukah happened. On Hanukah we can merit all five levels of the neshamah. The gematria of the names of the five levels of neshamah is equal to the phrase "lamed vav nerot shel Hanukah." (Yishmaelim pray five times a day.)
Vayeshev means to relax, to rest in peace and tranquility, but the stories are anything but. They are full of tragedies. Why is it called "vayeshev"? Right in the middle comes the story of Yehudah and Tamar which opens the way for the birth of Mashiach. And the miracle of Hanukah is hidden here. Out of all the tragedies of these stories comes the hope of Mashiach.
At the end of the parshah we see how all of the tragedies were working towards a wonderful end to provide a salvation for Am Yisrael. It's just the same now in our generation. Soon we will see how all of the tragedies that we are now suffering will end just as wonderfully. Shabbat shalom~