Shoftim, Devarim 17:9. Asher yihiyeh bayamim haheim. A Leader Has to Match His Community.

The passuk here says that in matters to which Torah law has relevance, one must consult the Torah scholars and leaders of one’s generation.

The Gemara in Rosh Hashanna 25a-b asks, "vechi sa’aleh al daitcho...’ would it have entered your mind that you should go to the leader of a previous generation? The answer is that "Yiftach bedoro kiShmuel bedoro." Yiftach, although he was a God-fearing man and a great leader, was nowhere near as great as Shmuel; even so, Yiftach in his generation is equal to Shmuel in his. Also there— even a ‘kal shebikalin,’ the most light-weight of spiritual leaders, once he is appointed on the tzibbur, must be viewed as an ‘abir shebe’abirim, ’ as if he towered over the highest of towering persons.

R’ Chaim Shmuelevitz discusses this in his Sichos Mussar, #40, pages 169-170: he says that the pshat is not that we have no choice because the earlier gedolim are not available. The pshat in Tosfos in R"h that says "ein lechoh ella shofeit she’hoyoh b’yomecho" is he is the right one, and the best one, for you. Then he brings from Koheles Rabboh 1:4:4 that if Aharon lived in the time of Yehoyadah and Tzadok, they would have been greater than Aharon– because for that generation Yehayodah would have been more fitting. Then he brings the story of Choni in Taynis 23a, where he awoke to find that many years had passed, and upon rejoining the grandchildren of his peers in the Beis Medrash, he began to say his divrei Torah, and they looked at him as if he were deranged. He became depressed, and said, "O chavrusa, o misusa", either people with whom I can study, or death. Reb Chaim asks, why didn’t Choni demonstrate to them his gadlus in Torah? He would immediately be made Rosh Yeshiva by enthusiastic acclamation! The answer is that his pshatim and teirutzim would not have made sense to them. Their reaction would not be one of awe and amazement; they would look at him as if he were a Baal Habos that knows a few things but is far from being a talmid chacham.

I think there is are two very important lessons here:

The first lesson:
The solutions that one generation uses to address a problem, and which are perfect for that time and place, should not be blindly followed in a different generation. You have to wisely and carefully assess whether the methods are still appropriate.

The second lesson:
If a Shul doesn't choose a particular Rav, or if the relationship is so dysfunctional as to inevitably cause a parting of ways, it does not necessarily reflect badly on the Rav or the shul— if Shmuel lived in the time of Yiftach, people would think he was not normal. You can’t have a rabbi that you think is not normal. Of course, it may be that the people aren't willing to hear mussar, and the Rav is exactly what they need. But it's also possible that that it simply is not a good match: what good is a rabbi that, to you, is really not nechshav leklum? You can’t taeineh on the people that they should respect him. For them, in fact, he is really out of place.

In a sense, this is similar to shidduchim. The best shidduch for one person is poison for another. I remember, when I was a bachur, that a friend of mine became engaged, and he was very happy with his kallah. A very close friend of his, whose initials are AH, was shmuesing with him, and he said, look, Ploni, you know I am your friend, and I realize how important a great yichus is, but my god, don’t you care what she looks like?

As a matter of fact, the chassan thought she was pretty. And he did marry her, and they lived, at least last time I checked, after thirty some years, happily ever after. I imagine that the friend’s comment was chilling, but he got over it.

(AH eventually got married, too, and in some people's opinions, his wife is nothing to be proud of, although I suppose it is very likely that if you think Secretariat was attractive, she's attractive too.)

Now, it is obvious that attractiveness and personality are judged subjectively, and they should be. For AH, the girl was a miuskaeit. For the chassan, the girl was pretty. What is less obvious is that leadership, in a manner of speaking, is indeed a beauty contest– in the sense that what is beautiful for one time and place, is completely inappropriate for another time and place.

My son shtelled tzu the story with Eliahu, which actually reflects both lessons discussed here. Hashem told him "ahd masai attah me’kanei es kinasi." ‘Ahd masai’ means that the time for kinah has passed, and different methods are needed for the hanhaggah of this generation. The time and place for Eliahu’s method of leadership had passed, and he had to leave this world.

Recently, the Yeshiva world had it's biennial Chavrusa Tumul, in which everyone gathers and decides who is going to learn with whom. Speaking of chavrusas and shidduchim, maybe this is the best way to choose a match. I wonder whether we can get a shidduch tumul going-- get the boys and the girls in one big room, and tell them that at the end of the day, you're leaving with one person, and that's it. Let them fight it out then and there.