In 1992—my junior year in college—I delivered a dvar Torah at a shalosh seudos, the gist of which was such:
The midrashim are all over Yaakov for his diplomatic overtures to his brother at the beginning of the parsha, if not for simply engaging in any diplomacy but not least for deigning to refer to himself as “avdecha Yaakov” [lehavdil, sounds a bit like some of the invective directed at our current President for his public displays of temerity in Suadi Arabia and Japan]. Didn’t Yaakov—who knew kol haTorah kula—know that “Halacha beyadua she’Esav sonei es Yaakov?” What was he thinking?
The midrashim quote from Rashi who explains that Yaakov was covering ALL his bases—“milchama” [as evidenced by “vayitzer lo”—his fear that he might have to kill in self-defense], “tefilah” [“hatzlieni na”] and “doron”, or “presents” [maybe, more accurately, “bribery”—and as shown in 32:16-17, this “mincha” involved a quite a bit of livestock]. The midrashim—some of the same ones who take Yaakov to task for making the overtures in the first place—then quote the gemara in Taanis [20a] that states that one should always be as flexible as a reed rather than rigid as a cedar. Yaakov covered ALL his bases—he didn’t favor one option over the other.
That’s where I left it then [I was referring, obliquely, to the nascent “peace process” at the time and the possibility that some people in our college’s frum community weren’t necessarily holding to the furthest-right political view.]
But there’s another part to the story. The midrashim explain why one should emulate the reed, rather than the cedar: a reed’s roots keep it grounded even as the wind blows it this way and that, while a cedar—no matter how strong—can be toppled by one very strong wind.
I’ll take that a step further: a reed’s roots are sunken—and hidden. A cedar [as many other trees its size and and stature] more often than not will have some of its roots exposed.
It is therefore likely less than accidental that, in between Yaakov’s preparations for and finally meeting Esav, Yaakov is faced with what some consider his signature spiritual moment: his encounter with the “Man”—which occurred at night, in the dark, away from everyone--and someone had to tell him that the struggle was over at first light, and it was Samael, who, while being simultaneously “sar shel Esav”, “Yetzer Hara”, “Satan”, and “Malach HaMaves”—is yet a messenger of G-d.
The first and obvious conclusion is to realize that anyone’s real struggles—spiritual or otherwise—take place “until dawn”, hidden away from everyone and everything.
But, more poignantly, there’s a hint about how “exposing” your “roots” make your approach more vulnerable, or indicate that they may be more tenuous than you think they are. In Yaakov’s case, his flexibility and discretion were almost interchangeable. For most other people, PDA—public displays of almost anything—make everyone uncomfortable. For good reason.