Flipped rapidly, starting with Jimmy Carter and gradually getting more conservative.
The ultra-Orthodox often vote as a bloc, i.e. the village of New Square for Hillary Clinton.
BTW, on his way out, Bill Clinton pardoned four New Square men convicted of fraud by falsely filing for various government grants.
I have a FORMER Conservadox friend who is former because he kept bombarding my inbox with pro-Obama email. He also sent pro-Obama email to other known conservatives, even though we told him to cut it out. Then HE acted as the insulted party! Shows how deluded he is. I told him, "If you were physically twisting my arm and I told you it hurt, you'd stop. If you are sending me emails extolling the non-existent virtues of an odious idiot, and I tell you to stop, why are you insulted that I tell you to stop?"
I know a lot of people in the Orthodox community, and they absolutely despise Obama, Schumer, etc. They are very conservative, as I said. Obama is basically a euphemism for Satan.
Speaking as an Orthodox Jew, I can assure you that the tilt toward conservatism is not limited to Chassidim. Torah observant Jews are disgusted with the downward cultural spiral driven by liberals. There are still some tendencies toward democrats among poorer communities that rely on government programs, but if not for that, they would definitely vote republican, the more conservative the better.
PS. Your old boss maya be a remnant of earlier generations when democrats were still relatively normal and patriotic and the Republicans still had the rep of being the party of the rich, WASPS and the Bircher Types.