I had discussed in a previous post that the purpose of Sefer Shoftim (or one of its purposes) is to show that the Jewish people needed a centralized leadership, as opposed to the pattern laid out in Chapter 3 of Shoftim, of the people serving God, straying, getting punished, crying out, and getting saved by a Shofet, a "Judge" whom God would save to rescue them, and then starting the cycle again.
We see, in the overall sweep of Sefer Shoftim, a decrease in quality of the leadership of the Shoftim themselves. The Shofet reflects the people. Thus, early on we have Yehoshua himself, we have Ehud ben Gera (who isn't presented negatively at all, although not much stands out), Devorah, who is presented in a very good light, judging the people and leading them, as well as instilling the confidence in her military (i.e. the general Barak) and inspiring the people in the praise of God (the Song of Devorah).
Gidon we already discussed, and while I presented his doubts as something that can give the modern Jew some comfort, at the same time, he asked for miraculous proof after proof from God Himself. And the 300 men who followed him didn't have that luxury. So while Gidon is still a strong leader, and of fine character (he turns down the kingship), he is arguably a step down.
Certainly, Avimelech, Gidon's son, is a big step down, murdering his brothers and seizing power.
Then we get to Yiftach and Shimshon. Yiftach is turned away from the people because of his lowly parentage, and leads a bunch of "empty men", presumably some band of outlaws. The people only want him to lead because they feel he is their only hope as a military leader. He agrees to save them only if he can then lead them. And he then impetuously offers to God the first thing that comes out of his gate, which, ironically, is his daughter. The Sefer leads us to understand that Yiftach actually killed his daughter in fulfillment of his vow. Certainly, this horrific act is a huge demonstration of the deterioration of the leadership of Israel. (Even if he didn't actually kill his daughter, the language of the text is such that we see it is a grave, serious mistake in judgment and values).
Shimshon lacks even what Yiftach had. Yiftach led the people, but Shimshon never seems to have had the Jewish people's interests in mind at all, even as he went about saving them. Chosen by God before his birth to be a Nazir, it seems God would have high hopes for Shimshon. Yet Shimshon has an eye for Philistine women (and is the first recorded example of a son to whom his parents say "Aren't there any nice Jewish girls you can marry instead?") and kills Philistines not because they are oppressing the Jews, but to get revenge for 1) figuring out his riddle, and 2) marrying off his first wife to another man after he had rejected her, and 3) for gouging out his eyes.
He turns to God, but it is always to avenge his own honor. Shimshon, though the favorite of elementary school boys because of his physical strength and military might, is the nadir of the Shoftim. We would never really be aware that he served as a leader except for a summary pasuk stating that he did (I don't have a Tanach in front of me, but I recall such a pasuk).
I'm not trying to "bash" our ancestors, to "diminish" our holy Tzadikim and point out their flaws. We have many holy ancestors (though only God is perfect), many of them in Tanach. But it seems that Yiftach and Shimshon are counter-examples, and part of a particular downward spiral.
Chazal certainly saw them on a lower level. In affirming that we must always be bound to the leadership of our time, even if our leaders are inferior to leaders of previous generations, the Talmud states: "Yiftach b'doro k'Shmuel b'doro", "Yiftach in his generation is like Shmuel in his generation". Yiftach was clearly an example of an inferior leader.
Of course, the monarchy, as we shall see in subsequent books of the Nevi'im, was not always successful either. But it at least offers the possibility of strong, righteous leadership, which the structure of the people in the period of Judges did not provide.
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