Eventually the elders of Gilead under threat from Ammon go to Yiftach and beg him to be their head and military leader. He eventually agrees and rules Israel fro 6 years. The question is, what was Yiftach's trait that attracted "empty men" to him and yet allowed him to be the type of leader Am Yisrael needed.
He Will Open
The word Yiftach in Hebrew means He Will Open. The men that came to Yiftach were empty. We learn in Perkei Avot in the 2nd Perek/5th Mishna that one who lacks fear of heaven is like a well. The Rabbeinu Yonah points out that this is an "empty" well. Later we learn that Rabbi Eliezer ben Horkunus is likened to a closed well that loses no water (i.e. Torah). By being filled up with the divine light a true chacham or leader has the ability to open the closed wells around him and fill them with the water of life or the Torah.
This was Yiftach's trait. He drew those empty of Torah and Emunah and filled them with HaShem's light. It was this trait that the elders of Gilead longed for in a leader and thus yearned for even when they saw it in a lowly "son of a harlot."
We know that every Rosh Memshelah of Israel is an empty vessel that is still considered the head of our political system. Just like the Medinah is an empty vessel void of the light of the Creator so to are its leaders. We need to pray that a true leader will arise and open our politicians eyes and all of Am Yisrael to the true light, the light of Emunah and Torah. When this happens no force on Earth can take away what by Divine Right belongs to the people of Israel.
The Medinah when filled with the light of the Creator will become the Medinat Malchut Melech HaMoshiach. This is the level where everyone and everything is reconnected to its true root, the pure divine light of the Creator. The light will be so strong it will cover the world. With HaShem's help we will be led with proper leaders, filled with the divine light of Moshiach.