In Yaakov's prayer to G-d to save him from 'the hands of Esav', he prefaces it by expressing how little he deserves G-d's benevolence since he feels diminished by the disproportionate kindness he has already received.

As evidence Yaakov mentions how despite when he first crossed over the Jordan River on his way to Lavan all he possessed was his staff, now he has developed into two full camps.

כי במקלי—for with my staff, עברתי את—I have crossed, הירדן הזה—this Jordan (בראשית לב יא)

The Targum Unkelos translates במקלי as יחידי, alone, without any possessions or wealth other than his staff.

Why the emphasis on his retaining only his inconsequential staff? Simply stating לבדי—alone, would have been sufficient to make the point.

Rabbeinu Yaakov, the son of the Rosh, known as The Tur, in his commentary on Torah ponders the accenting of הירדן הזה—'this' Jordan [River]. The word הזה generally refers to something in one's presence, yet Yaakov at this juncture was quite far from the border of the Land of Israel and simply reminiscing a distant event that occurred in a location far from where he was presently standing.

In the Prayer for Rain we recite on Shemini Atzeres, we request abundant water in the merit of our ancestors.

In the paragraph that appeals in the merit of Yaakov we say: זכור טען מקלו—Remember the one who carried his staff, ועבר ירדן מים—and crossed the Jordan's water. Some suggest this refers to the Midrash that tells of the miraculous splitting of the Jordan as Yaakov placed his staff upon it. If that’s the case, then it was a miracle performed by G-d for Yaakov's convenience. In what way does it exhibit special exertion on Yaakov's part that would merit water for his descendants in the future?

The Talmud tells us that the ירדן—Jordan River, is thus called because the river stems from a region in the north that is the territory of the tribe of Dan, ירד דן— it descends from Dan.

In the teachings of the great Gaon of Vilna, the Gr'a, it is taught that this river corresponds to a heavenly river known as נהר דינור—a River of Fire, which is in the heavenly sphere that serves as the boundary between those who depart from this world and must traverse this body to enter Gan Eden. Similarly, the Jordan River is the exit and entry point to the Land of Israel.

When one leaves the sanctified environment of our land one is susceptible to ירידות—descension in their spiritual stature.

The tribe of Dan is referred to as the ירוד שבשבטים—the descenders among the tribes. Historically, they travelled last in the procession in the journeys in the desert. They succumbed to idolatry as evidenced in the Idol of Micha that was situated in territory of Dan, and the very first blasphemer who was associated with this tribe.

Yet, ironically, it was this tribe who is also known as the מאסף לעל המחנות—who gathered and inspired those who were expelled from the Clouds of Glory.

In the blessing to this tribe, Yaakov extols their yearning for salvation, in a verse we often recite: לישועתך—to your salvation, קויתי ד'—do I long, Oh Hashem.  

Rabbeinu Yonah writes in his Shaarei Teshuva: And one who trusts G-d should hold on during the vision of his distress; for the darkness will be the cause for the light - as it is written (Michah 7:8), "Do not rejoice over me, O my enemy; since I have fallen, I rise again; since I sit in darkness, the Lord is my light." And our Rabbis, may their memory be blessed, said (Midrash Tehillim 22), "If I had not fallen, I would not have risen; If I had not sat in darkness, the Lord would not have been my light."

Even among the darkest of the tribes, there beats a heart filled with yearning, that at times is compelled by the descent to rise like a lion, defiantly, drawing ever closer to G-d.

We each have our lonely moments of descent. But as Yaakov, despite being alone and seemingly helpless, fought off the notion of הירדן 'הזה'— not simply a physical barrier of water, but rather a slippery slope of descent, overcoming it alone with only his staff.

The Paneach Raza, one of the great Rishonim, reveals that this staff was hollowed out and filled with olive oil to fuel his lamps so he may study Torah at night.

It wasn't simply his commitment to study Torah that is being extolled, but more so his never ending yearning for closeness to Hashem no matter what ירידות—descension he faced.

The Chasam Sofer points out the word for Yaakov's staff—מקל, is an acronym for מעולם קוינו לך—We always put our hopes in you.

Yaakov when stating his experience years prior of crossing הירדן הזה—this Jordan, was not a reference to the actual location, but rather to the challenges he was still facing in 'this prolonged descent', until such time as he will merit to cross into the safety of the holy land once again.

This 'eighth' portion in the book of Breishis, is the prelude to Chanukah.

In the darkness of the exile of Yavan, despite having descended to the lures of their culture, we brought ourselves around, prodded by the darkness to rediscover the closeness we possess with the Almighty.

May we cross all our rivers with a fervor that can never be extinguished!

באהבה,

צבייהודה טייכמאן