(This Dvar Torah follows on from the previous one)
The Gemara in Rosh Hashanah (25b) teaches, that Yiftach in his generation was like Shmuel in his generation. The Shofet Yiftach is a very enigmatic Biblical personality. He was not what we would call the greatest man who ever walked the face of the earth. He certainly was not anywhere near the caliber of the navi Shmuel. Shmuel HaNavi stands out in a Tanach full of great people as one of the dominant personalities of Jewish history. When Chazal say that Yiftach in his generation was like Shmuel in his generation, they are trying to convey that Yiftach was not on the level of a Shmuel, but every generation must live with the leader it has. Therefore, the people living in Yiftach’s generation had to give him the same honor and deference as if he was a Shmuel HaNavi.
This is the simple interpretation of this Gemara in Maseches Rosh Hashanah. The Dubner Maggid quotes a Medrash in Koheles. According to this Medrash the intent of the Gemara is the reverse: Had Shmuel lived in the generation of Yiftach, he would not have been considered to be anything special. This is mind-boggling, because we see in the story of Yiftach that Yiftach made some terrible mistakes in his life.
The Dubner Maggid explains that the Medrash does not mean that Yiftach was greater than Shmuel. Shmuel was far greater than Yiftach and most other people. The Medrash means that every generation needs a leader to whom they can relate. Sometimes, a leader can be TOO BIG for his generation. He could be too far above them and too removed from them to lead them properly. The Duber Maggid, in his inimitable fashion, gives a parable to explain this:
Just like the clothes a person wears cannot be too small on him, so too the clothes a person wears cannot be too big on him. Someone who is a size 42 who wears a size 56 suit will not be properly dressed! That is the way it is with leaders as well. The leader needs to be appropriate and fit the particular generation he is leading.
The Dubner Maggid explains that had Shmuel been in the generation of Yiftach, he would not have been an effective leader because he was too spiritually superior to that generation. The people could not have related to him.
This is the same idea as we mentioned above. If leaders are too far above the level of the people, they will not be able to function as role models. “Augh! He is too above us. He is a malach! We need a human being!”
