It’s not a perfect analogy, but the stories of two improbable leaders are remarkable for their similarities.
Taken from the Book of Judges, this week’s Haftorah portion (https://www.chabad.org/parshah/article_cdo/aid/696127/jewish/Haftorah-in-a-Nutshell.htm) tells the story of Jephthah, the son of Gilead, and a prostitute.
As Gilead marries a woman who bears him two “rightful” male heirs, the “legitimate sons” chase Jephthah from the family’s properties.
“You shall not inherit in our father’s house as you are the son of another woman,” they tell him.
Jephthah’s flight from the family takes him to the city of Tob, where he gathers around him a collection of shady characters, making a living doing what criminals do.
The affluence of Gilead and its people in time attract the attention of Ammonites, who waged war on the entire People of Israel.
Faced with existential destruction, elders of Gilead reached out to one with ties to them, but one accustomed to scuffed knuckles and raiding parties. One who had look danger head-on and prevailed over it.
“Did you not hate me and drive me away?” Jephthah asks them.
Yes, we did, they acknowledge; but the elders offered to make him their leader if he could lead them to battle against the Ammonites.
Which he did.
It is interesting to note that, “Jepthah tried to bring a peaceful resolution to the conflict by sending messengers to reason with the king of Ammon; but the latter remained inflexible.”
When all that remained was taking up arms, it was Jepthah who led the tribe of Gilead to victory over Ammon.
It goes without saying that roughly three thousand years later, the voters of America have reached out for another atypical leader. One who had taken an inheritance of outer-borough apartment properties, building it into one of the nation’s largest real estate fortunes. One who would be asked to lead the nation into struggles with China for economic supremacy, with Iran and North Korea for military survival, and with the task of rebuilding a national economy and employment market.
The lessons of Jephthah are mixed. Orthodox Union concludes (https://www.ou.org/torah/parsha/shnayim-mikra/chukat_haf/)
Jepthah was poised to deliver a lesson for all times. A man of flawed and difficult familial background has been put into the crucial position of leading a segment of the Jewish people when they must confront “cousins” who refused to honor their family connections. He succeeds partially, but had he been able to respond to the elders’ request magnanimously, had he been able to see the good of family even without a personal experience of it, he might have delivered the kinds of messages about God that Samuel delivered, where God’s centrality would become clear not only to Jews but to non-Jews as well.
He fails in that he only does ok, when he stood on the threshold of greatness. Unable to transcend himself, he goes into history as a leader (as he demanded), but not one who leaves the legacy he might have.