Yosef was lost somewhere in Mitzrayim, "vayeired Yehudah," Yehudah lost his leadership position for his role in the fiasco, Reuvain was immersed in doing teshuvah for his sins, Ya'akov could not be consoled over the loss of Yosef -- could things get any worse? Could things look any bleaker? Yet, the Midrash (85:1), after going through the above list, tells us that while all this was going on Hashem was busy creating the ohr of mashiach. At the very moment when things look the bleakest, Hashem was crafting redemption. That's a great lesson about Jewish history and Jewish destiny.
We have the story of Yehudah and Tamar in our parsha. The gemara (Sotah 7b) darshens that there is a connection between Yehudah's bracha, "V'zos l'Yehdah...," with a connecting vav, in parshas V'Zos haBracha, and Reuvain's bracha that comes right before it. Yehudah was not allowed to enter gan eden after death because he had pledged his olam ha'ba as collateral in case he did not bring Binyamin home. Moshe Rabeinu wanted to rectify that. He asked that Hashem open the gates of heaven for Yehudah in the merit of the special zechus Yehudah had of causing Reuvain to admit his guilt. When Yehudah publicly admitted that he was the one who had been with Tamar, Reuvain was inspired and admitted his own guilt in being "bilbeil yetzu'ei aviv" with Bilhah. In that merit, Yehudah earned entrance to gan eden.
R' Leib Chasman makes a beautiful point. Why it is that Yehudah's own public admission of guilt, at the cost of great embarrassment, was not enough to earn him olam ha'ba. Why was it only the fact that he caused Reuvain to confess? He beautifully answers that it's not only our own tzidkus that ultimately defines who we are, but it's what impact and influence we have on others.
Be that as it may, I don't understand simple pshat in a Rashi on this sugya. The gemara says that Yehudah and Reuvain received reward in this world as well as the next. Rashi (d"h lahem levadam) writes that Yehudah received the reward of malchus; Reuvain received the reward of getting the first portion of land in Eretz Yisrael, in Eiver ha'Yarden. Putting aside the question of whether Eiver haYarden has a full kedushas ha'aretz, I don't understand why this is a reward. In Parshas Matos Moshe Rabeinu was highly critical of Reuvain and Gad for asking for that territory. Taking it was viewed as a negative, and it was only with great reluctance that Moshe agreed that they could settle there. Why is getting that land a reward? I don't know.
It takes two to tango, and the reward of malchus given to Yehudah was earned by Tamar as well. Rashi (38:26) quotes the Midrash that "because Tamar was modest in her in-laws house, therefore I [Hashem] decreed that she should produce kings of Israel."
The is an amazing Rashi given the context. Here Tamar says, "haker na," whoever these items belong to is the father of my baby. She deliberately avoided accusing Yehudah directly, and would have even been willing to give up her life rather than embarrass him in public should he refuse to admit guilt. Yet, that's not why Tamar earned the reward of malchus! It's because of her tzeniyus, not her mesirus nefesh, that she was deserving of producing kings.
Were I a Beis Ya'akov teacher, this would be an easy home run derasha for the week. "Kol kevudah **bas melech** pnimah..." (The 45:14) The midah of tzeniyus and the midah of malchus go hand in hand. (Why that should be so is something to explore further. Friday night is a long night -- plenty of time to think : )
The Midrash writes that Yehudah took no notice of Tamar at first, but a malach caused him to turn aside off the road and go to her. He was coerced somehow to fall into this situation so that malchus yisrael could arise. It sounds like a supernatural occurrence, a long shot that you would not bet on. So what was Tamar thinking? What was this girl, who was so tzanu'a, hoping for? Surely she could not have expected Yehudah to notice her or to be with her? It would be like hoping to win the lottery!
R' Chaim Shmuelevitz (Sichos Musar 5733 #9) answers that when a person realizes great things are on the line, he/she will grasp at every straw and make every effort, no matter how slight the chance of success, to bring things to fruition. Tamar realized this was her chance -- a slight chance, but still, a chance -- to perhaps be the mother of malchus, the mother who will bring the lineage of mashiach into the world. No matter what the odds, no matter what effort she took, it was something she had to shoot for.
Still haven't had a chance to write about Chanukah -- never enough time.