The setting could not have been more revealing. It was almost too poetic, too perfect, to have been hand-crafted by anyone other then that rascal fate. As the Holy day came to a close, the congregants of one particular Chicago shul were moving past the guilt and atonement toward somewhere a little more uplifting. Hatikva replaced the Ne’ila prayer on their lips and life slowly began to ebb back into the room. At the back stood two of the more towering personalities, both larger than life, both seemingly too big to share the hallowed chamber they both stood in. One a former high-ranking Obama official, the other, a local businessman and patron of Israel’s settlement enterprise and active supporter of the Gush bloc.

The businessman, wrapped tightly under in his white and orange striped talit, a gift from the Rabbi of Gush Katif many years ago, uttered the words with a touch more zeal and personal allegiance than you would normally expect to see from the politely Midwestern modern-orthodox around here. Those words, carefully recited, To be a free people in OUR land, the land of Zion, and Jerusalem, meant a great deal. You could see it in his eyes, the intensity, the fire. But there was also a hint of appreciation, albeit a small one, as he looked up at the former government official who had made it a point to come and be with his congregation. But with each verse, that faint, initial glimmer of appreciation, gave way to a sort of bitterness which probably could not have been diminished had the former administration official led the congregation in Israel’s national anthem with Itzhak Perlman and Ofer Nissim on his flanks. A day of judgments indeed. But the feeling was not unique to those two, most people were aware of it. The real preoccupation it seemed, the one everyone’s hunger paled to by comparison, was the reason behind the stress on the relationship of these two men; the President’s handling of Israel.

Yom Kippur, transgressing, the recognition of sins and the righting of wrongs, it’s a difficult exercise. And more so for some. We sinned, we stole, we became violent, we caused others to do evil. Tov, say sorry, maybe go the way of a burnt offering, pay a charity. There are things you could do to clear your slate. But then again, there are those who would disagree. Such as the aforementioned businessman.

For the sin which we have committed before You under duress or willingly.

We froze your covenant with our forefathers and stopped populating the entirety of the Land, but he threatened to withhold our fighter jets and loan guarantees. What could we do?

And for the sin which we have committed before You by hard-heartedness

He doesn’t get it! These Arabs want to see us try and swim to Cyprus. But no matter how we tell him, he just doesn’t understand our concerns.

For the sin which we have committed before You by using coercion.

How dare he threaten us and try and force us to outsource our security. Mamzer!

So why is this Yom Kippur story still relevant? Because this is Chicago. This is the President’s hometown, where he and his advisors are from and maintain many relationships. These shul-goers, more than any others, are the President’s Jews. After debates, campaign stops, tv and radio ads, Chicago’s Jews are as divided and opinionated as I’ve ever seen them as their true Day of Judgment stands only few short weeks away. Many have known President Obama, or some of his key advisers for years. They supported his rise, and opposed it, since he was an up and comer in this town. It’s said that many Americans do not feel that the President is one of their own, a sentiment I should stress is not at all felt in Chicago. He is looked upon very much as a their guy, their native son.

The President’s relationship with Israel, and all that entails, has made the Jewish state a hot-button issue in the Presidential campaign yet again, and is a big factor in how many Jews will vote. Many of the slogans I overheard again and again, were that in an election it’s America first, and Israel second. Naturally this was countered with “if that’s your argument, then what you’re really saying is that it’s America first and Israel tenth.” “We are Jews, we should vote for the best interests of the Jewish people and not social justice and all that other chazerai.” The Malevolence is palpable, but so is the pride. There is a long standing tradition of the Jewish vote going to the Democrats. It’s not the economy, but the idealism, stupid. Maybe John Kerry and Al Gore didn’t seem as exciting as Obama did 4 years ago, but they espoused the same brand of Liberal politics and received many of the same votes Obama did, giving credence to the argument that Jews will vote for pressing American matters, not Israeli ones. Obviously not everyone here feel that the President is guilty of frivolity, tale-bearing, causeless hatred and a confused heart. No lashings, excisions, or karet of any kind are being prescribed. Rather, they look upon Obama as the embodiment of their Democratic brand of politics, firmly rooted in a Liberal idealism, with the cherry-on-top attitude of appreciation that he is a strong supporter of the State of Israel. These Jewish Chicagoans prayed hard that Obama’s presidency should be inscribed in the Book of Life.

The Jewish vote will be a contested and very important one come November, and whether it swings toward social issues, national security issues, taxes, healthcare, Israel or Palestine, one thing is for certain at this point. The vote is undecided. So national correspondents be warned, if you want to get the inside track on how the Jews are going to vote, pack your bags and head to La Guardia and Miami International immediately. Because Chicago is the most fertile ground for sampling the Jewish vote.