Rabbi Jonathan Roos at Temple Sinai in Northwest Washington practices his sermon on Friday in advance of the Jewish new year, which begins Sunday night. (Evelyn Hockstein/For The Washington Post)

The holiest day of the Jewish year falls less than a month before the most anticipated date on the 2016 political calendar. Oct. 12 is Yom Kippur, and Nov. 8 is Election Day.

So when rabbis speak from the pulpit to their largest audiences of the year, what are they going to say about Hillary Clinton and Donald Trump?

It’s a question Jewish leaders are mulling all over the country, as the Jewish High Holy Days begin with Rosh Hashanah on Monday, followed by Yom Kippur 10 days later. Each of the holidays draws flocks of American Jews who rarely set foot in their synagogues the rest of the year. And in most of those synagogues, the rabbi’s sermon is the most anticipated part of the service.

“Everybody is really struggling with this issue. Everybody. No matter where they come out about it,” said Rabbi Julie Schonfeld, the executive vice president of the Rabbinical Assembly. “They became rabbis because they want to make the world a better place. Figuring out how to be the greatest force for good during a polarized election season, on the High Holy Days, is a question that each rabbi best answers in a very unique way.”

Some rabbis want to speak out strongly against Trump, who has alarmed much of the Jewish community with his views deemed as racist and possibly anti-Semitic. Those rabbis are weighing how clearly they can express their concern about Trump’s candidacy without breaking Internal Revenue Service rules that say tax-exempt congregations cannot endorse a candidate, though rabbis can express their viewpoints on political issues and can personally endorse when they’re not representing their congregations. Some are even considering putting IRS rules aside and endorsing Clinton, given what they consider to be the high stakes of this election.

Other rabbis worry about offending Republican congregants. Or they wonder if the most sacred days of the year should be about spiritual reflection, not worldly political fights.

For Gil Steinlauf, the senior rabbi at perhaps America’s most political synagogue — Cleveland Park’s Adas Israel, where President Obama gave his only speech in a synagogue, and two Supreme Court justices worship on the High Holy Days — the answer was clear.

Steinlauf said he will speak about the election on both Rosh Hashanah and Yom Kippur.

“I’m going to directly encourage people to get out and vote. Not only that, but I’m going to directly encourage people to do what they can to help other people in other states where there are various social and cultural forces that prevent them from making their way to the ballot box … to not be passive, to take action here, because so much is at stake,” he said. “I am lifting up a Jewish discussion of the times that we live in.”

Politically connected Republicans and Democrats alike worship at Adas Israel, and Steinlauf said he usually strives to make them all feel at home. But in this election, he’ll be preaching to a packed house with very few Trump voters, he expects. Less than 20 percent of Jews say they will be voting for Trump, and those voters are more concentrated in the Orthodox Jewish community. In the District of Columbia, finding any Trump voter is a challenge.

“Because there is an almost unanimity about the outcome of this election, what this community is interested in, I don’t have to give a sermon where I’m hinting at something, as much as meeting the congregation where they are and addressing what we can do,” Steinlauf said.

Jonathan Roos, the senior rabbi at Temple Sinai in Northwest Washington, knew many months ago what he would be talking about when October came around.

“I thought, ‘Well, if Trump is still in this by the time the general election comes, it’s definitely going to have to be a High Holy Day topic.’ ”

Roos read Rabbi Eric Yoffie’s op-ed in the Israeli newspaper Haaretz probing the question of whether rabbis have a moral responsibility to break the IRS rules and endorse a candidate this Rosh Hashanah. “Perhaps it is time for rabbis to put the usual niceties aside, recognize the emergency nature of our situation, and come out for Hillary on the holidays,” wrote Yoffie, a former president of the Union for Reform Judaism, America’s largest denomination.

Yoffie ultimately recommended a sermon based on principles but not an explicit endorsement, but Roos said that many of his colleagues on rabbinical listservs and Facebook groups have been talking about endorsing. In previous years, Christian pastors who think they should be able to endorse have flouted the IRS rule on a day they call “Pulpit Freedom Sunday.”

For his part, Roos decided not to try to spur his congregants to political action but to use the election as a way to make them look inward. “Are there things that we accuse other people of, wrongdoings that we think are so publicly visible about one candidate or the other, that we’re actually guilty of ourselves?” he will ask. “Take the blanket idea of identifying a group of people and keeping them out of our lives. . . . Just because we haven’t literally built a wall to keep people out doesn’t mean we’re not guilty.”

He said he thought that was a better focus for his sermon in front of about 2,000 congregants at Temple Sinai. “I absolutely think who gets elected is of tremendous importance. I don’t think I’m the person who should be weighing in on that.”

That’s a debate many rabbis are having, said Rabbi Rick Jacobs, the current URJ president. “A rabbi is not an op-ed columnist. What do we uniquely bring to the conversation that you’re not going to get by reading a really smart, really well-informed journalist? A lot of rabbis are thinking, what’s my value to add?”

Jacobs thinks that most Reform rabbis, in the United States’ most numerous and generally most social-action-focused denomination, will speak out about political issues in a way that suggests congregants should go vote based on those issues.

“It’s a moment to try and tilt the world to the most profound Jewish values. I don’t have to weigh in and say a candidate’s name to say that the issues that matter most to our community are on the line,” Jacobs said. “I think that could not be more evident.”

But not everyone agrees. Rabbi David Greenspoon at Congregation Sha’are Shalom, a Conservative synagogue in Leesburg Va., said he’s afraid he would be seen as endorsing a candidate if he even talked about issues or values. He knows that in his 150-family congregation, at least 15 or 20 Trump voters will be listening in the pews.

“People would be on the edge of their seats waiting to pounce” if he talked about the election, Greenspoon said. Instead, he’ll talk about parenting children and about caring for elderly parents.

“You can’t put on Sean Hannity and hear what I’m going to say. Because he’s talking politics, and I’m talking Torah.”

Rabbi Daniel Zemel at Northwest Washington’s Temple Micah won’t be talking about the election either, but not because he fears disagreement. It’s agreement that turned him off the subject — he thinks nearly everyone in his congregation is already voting for Clinton.

“For me to tell people what their values are about the election, it would be so preaching to the choir in the most unnecessary way,” he said. Instead, his talk on Rosh Hashanah will be inspired by Sebastian Junger’s book “Tribe,” which the congregation is currently reading. (Earlier, Zemel assigned Ta-Nehisi Coates’s “Between the World and Me,” and members of the congregation gathered this summer for a discussion about racial justice.)

On Yom Kippur, Zemel will stick to theology, preaching about the Book of Job.

“If I thought I was going to be addressing a room where even 10 percent were wavering, then maybe” he would talk politics, he said. “Do we really think there are that many undecided voters who are Jewish? I don’t think so.”

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