Reluctance to Send Benjamin
Joseph, though sold by his brothers into slavery in Egypt, has risen to the position of Viceroy.  The Pharaoh has placed him in charge of feeding the world in a time of devastating famine. Jacob sends all but one of his sons to purchase grain in Egypt. He does not send Benjamin though “because he said, ‘Perhaps a fatal accident will occur to him.’”
When the brothers finally make it to Egypt they are confronted by Joseph, whom they do not recognize as their brother. He feigns hostility, accusing them of being spies. Joseph demands that they bring their youngest brother, Benjamin, back to Egypt with them; otherwise they will no longer be welcome. In addition, he demands their brother Shimon as a hostage.
When Joseph’s brothers returned home, they told Jacob that the viceroy of Egypt required that they bring Benjamin to him. Jacob demurred, saying “You have bereaved me! Joseph is gone, and Shimon is gone, and you want to take Benjamin!.. his brother is dead, and he is the only one left. A fatality will occur to him on the way…”.
Finally, when the family has exhausted their food supply, and Yehudah has given his guarantee of Benjamin’s safe return, Jacob relents.
Why was Jacob so concerned about Benjamin’s safety? And why did he finally accede to the demand to send him when Yehudah guaranteed his safety?
Rashi addresses the first question and answers: “From here we deduce that the Satan makes accusations at a time of danger.” Satan represents the destructive forces of evil that prey on us when we are most vulnerable.
However, the question has been raised, why was Jacob concerned only with the danger to Benjamin’s life and not the lives of the other brothers?
One answer is (see Likkutei Sichos volume 5. P. 213ff.) that Rachel passed away and was buried  on the road back to the Land of Cana’an, and Joseph, likewise, disappeared when Jacob sent him to inquire the peace of his brothers. Jacob was particularly concerned that the Rachel branch of his family was particularly susceptible to the dangers of traveling.
We may still ask a question: What persuaded Jacob to send Benjamin after Yehudah took full responsibility for his safety? Could the promise of a mere mortal remove one’s vulnerability to the perils of the Satan?
Fear of Traveling: Loss of Legacy
One may see Jacob’s reluctance to send Benjamin as more than the fear that he could lose another child. Jacob was deeply concerned that Benjamin’s loss would mean the loss of his own legacy. This particular fear did not arise with respect to his other children. In addition to the family history of tragedy on the road, to Jacob his son Benjamin represented both the future of the Jewish nation and its shield against the Satanic forces that would repeatedly try to cripple us on our journey.
Only Yehudah was able to convince Jacob that, come what may, nothing dreadful would happen to Benjamin and, by extension, Jacob’s legacy.
We must now try to understand what it was that was so unique about Benjamin and how Yehudah was able to assuage his father’s concerns.
Jacob stayed in his uncle Laban’s house for 20 years. It was only when Joseph was born that Jacob decided to return home. Indeed, our Sages tell us that Jacob was “punished” for the 22 years (the 20 he stayed with Laban and the two years of his journey home) during which he did not observe the Mitzvah of honoring his father and mother. Why, indeed, did he wait so long?
Jacob wanted to delay his return as long as possible to avoid reopening the dangerous conflict with his brother Esau. G‑d predicted this intense conflict even before Jacob and Esau were born, as the Torah recounted in an earlier parsha. What power did Jacob have to ultimately prevail over Esau? The answer is provided by our Sages in the Talmud (Bava Basra 123b) and Midrash, cited by Rashi, on why Jacob waited until Joseph was born.  He knew that it was Joseph who possessed the power to vanquish Esau. In the prophetic words of Ovadiah: “And the house of Jacob shall be a fire, and the house of Joseph a flame and the house of Esau for stubble.” Fire without a powerful flame does not dominate at a distance. Once Joseph was born, Jacob trusted in G‑d and wanted to return home to his parents.
Joseph possessed the unique power to overcome the threat from Esau. Chassidic literature asserts that Joseph’s soul transcended both Jacob and Esau’s souls and was therefore not threatened by Esau’s power, unlike Jacob’s own soul.
When Joseph disappeared, Jacob hoped that his power would be transferred to his younger brother, Benjamin. Though not possessing a soul as lofty as that of Joseph, Benjamin would nevertheless share some of his characteristics. In the terminology of Kabbalah, Joseph was the “upper tzadik” and Benjamin the “lower tzadik.” Joseph possessed the ability to transmit this transcendent power down to the lowest of levels; Benjamin was similarly able to transmit his inferior transcendent power in the inverse manner, by elevating and uplifting the lower level.  
Jacob’s concern was not just for the present but also for the future. His success as the father of the Jewish nation depended on his ability to remove, repair or sublimate the obstacles on the path to Mount Sinai and from there to the Messianic Age. Without Joseph, Jacob depended on Benjamin’s ability to accomplish the same goal, albeit with less intensity.
Jacob’s reasonable fear was of a mishap that Benjamin might suffer while he was traveling. The danger of losing Benjamin on his trip from Cana’an to Egypt threatened to undermine our journey towards the final Redemption; the path is riddled with obstacles precisely because it’s destination is so critical. In G‑d’s system, the greater and the more crucial a goal is the more obstacles will appear on the way towards fulfillment of that goal, necessitating greater persistence and fortitude.
Yehudah’s Guarantee
It was only when Yehudah guaranteed that he would return home with Benjamin that Jacob felt able to send his youngest child off to meet the Egyptian viceroy.
What was it about Yehudah’s guarantee that overcame Jacob’s apprehension? 
Yehudah was to be the progenitor of King David and his dynasty of leadership that would endure until Moshiach. Other kings and leaders were also destined to emerge and provide leadership, for better or worse, for the Jewish people. What is the difference between the Davidic dynasty and the other leaders?
Two Forms of Leadership
There are two forms of leadership; functional and essential, or, extrinsic and intrinsic. Most leaders are created by the people they lead. If a group of people proclaim someone as their leader this individual is thereby empowered to lead and govern. The people’s devotion to their leader helps him unleash whatever hidden talents he may have. Those chosen for leadership roles become leaders because they have been anointed by the people and they function as such. But leadership for them is not intrinsic to their existence.
The kings of the Davidic dynasty, particularly the Moshiach, by contrast possess intrinsic and essential royalty. Their power of leadership transcends that of Joseph, because no obstacle can possibly deter it. While Joseph is likened to a flame which will consume the straw, Yehudah transforms obstacles for good and brings that goodness into the Messianic Age.
This concept of bringing the obstacle into Redemption is illustrated with the following anecdote:
A truck driver was driving along on the freeway.  He passed a sign that said "low bridge ahead." Before he knew it, he got stuck under the bridge.
A police car pulled up.  The officer got out of his car and walked around to the truck driver, put his hands on his hips and said, "Got stuck, huh?"
The truck driver said, "No officer, I was delivering this bridge and ran out of gas!"
There are two ways we can look at the obstacles we encounter on our way to Geulah-Redemption: The first approach is to view them as an impediment that we must struggle to surmount. We believe we must do something to blow up the bridge or lower the highway. That is how most great leaders deal with obstacles; they try to plow right through them.
The alternative path is to view the obstacle itself as an important part of our mission. We can and should take it with us on our trip and deliver it into the Messianic Age. A postman cannot wish for there to be no mail to deliver because then he’d be out of a job. Our spiritual job is to deliver the obstacle.
When Jacob heard the conviction and certainty in Yehudah’s voice, he detected the spirit of Moshiach and knew that Yehudah would succeed in the immediate task of bringing Benjamin back safely and, in so doing, ensure the final redemption.
Yehudah (read: Moshiach) would certainly be assisted by Joseph and the other great leaders who have battled all forms of adversity to facilitate our continued survival in exile and pave the way for Redemption. However, only Moshiach can enable us to reach our final destination; he is the only one who can guarantee success and empower us to transform all obstacles into positive forces.
Chanukah Live
This week’s parsha is always read during Chanukah and there is a deep connection between the two.
The light of Chanukah, wielded by the holy and courageous Maccabees, was able to destroy the Syrian-Greek obstacle. But, alas, it was only a matter of time before the next obstacle appeared. Nachmanides states that when the heroes of Chanukah, notwithstanding their righteousness, failed to install a leader from the House of David, the victory of Chanukah could not last. Chanukah had many of the trappings of the Final Redemption; there was a rededicated Bais Hamikdash-Holy Temple and no subservience by the Jewish people to another nation. The crucial element missing was Moshiach, the leader who possesses intrinsic and essential leadership. The Hasmonean dynasty was eventually destroyed and the Roman hegemony began, leading our people to the present state of exile. If the Maccabees had restored leadership to the descendants of Yehudah and David, the light of Chanukah would have transformed the darkness into light and endured forever.
It is up to our generation to complete the task of bringing on the Redemption by greeting Moshiach in our Chanukah celebration, and “he will redeem us!”