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Al Smith Dinner Could Be Especially Awkward for Clinton, Trump

Watch Live: Clinton, Trump Attend Alfred E. Smith Dinner

Moderator Chris Wallace concluded Wednesday night’s final presidential debate with a note of relief for Hillary Clinton and Donald Trump, who refused to even shake hands at the beginning of the night. “This is a final time, probably to both of your delight, that you're going to be on the stage together in this campaign,” Wallace said.

But they will share the stage one more time, just 24 hours after their last meeting.

The white-tie Al Smith Dinner, the major fundraiser for the Catholic charities connected to the Archdiocese of New York, has attracted presidential candidates for years and traditionally offers a rare moment of levity in the midst of heated campaigns where candidates poke fun at each other and themselves.

It can be an awkward event in any election year, but exponentially more so this time with two candidates who dislike each other more than perhaps any others in modern history.

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At the 2012 dinner, Mitt Romney poked fun at a Barack Obama gaffe by saying the president would tell St. Peter “you didn’t build that” after he founded the church. Obama joked about Romney’s wealt by saying that while he went shopping "at some stores in midtown,” Romney went shopping “for some stores in midtown."

Post-debate Trump out on trail 6:53

But the candidates typically close on some gracious praise for their rival.

“We don’t carry the burden of disliking one another,” Romney said of Obama, whom the Republican said “has many gifts and a beautiful family that would make any man proud.”

“In our country,” Romney continued, “you can oppose someone in politics and make a confident case against their policies without any ill will.”

Obama, for his part, said he “admire[d]” Romney’s family. “We may have different political perspectives, but I think — in fact, I’m certain — that we share the hope that the next four years will reflect the same decency and the same willingness to come together for a higher purpose,” Obama added.

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It’s almost impossible to imagine Clinton or Trump saying something similar of each other Thursday night.

“In theory, it’s supposed to be like the handshake before the big game,” said David Litt, a former Obama speechwriter who worked on the president's 2012 Al Smith speech. "Unfortunately, this year that seems absurd.”

For Clinton, there’s little desire to even joke about Trump, at the risk of normalizing him, especially after he refused to commit to accepting the results of the election in Wednesday night’s debate.

“She has a really tough needle to thread,” Litt said. “She has to poke fun in some ways at Donald Trump without making it seem like his comments are just a big joke.”

What does Clinton need to do next? 4:29

Skipping the dinner would mean running afoul with Timothy Dolan, the powerful Catholic Cardinal, as well as the city and state’s political establishment — a non-starter, especially for two New York candidates.

“Offending the church by not appearing was just something you did not do,” said Hank Sheinkopf, a New York Democratic strategist who said historically, the dinner has been a critical part of any candidates’ strategies for winning over Catholic voters nationwide.

Walter Mondale’s decision to skip the dinner in favor of debate prep in 1984 was seen as damaging, but at least wasn’t booed like Jimmy Carter in 1980.

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But Sheinkopf said Clinton may be better off just ignoring Trump. “She doesn’t have to talk to Donald Trump or about Donald Trump at all,” he said, suggesting Clinton focus on the dinner’s charitable mission.

Trump’s approach is more of a mystery. He’s shown little appetite for the kind of self-deprecating humor that makes a successful Al Smith appearance. And his harsh jabs at Clinton may feel out of place feet surrounded by Catholic prelates.

The room will also be packed with many of Trump’s archenemies. Beyond Clinton, there will be Michael Bloomberg, who excoriated Trump at the democratic National Convention, and New York Attorney General Eric Schneiderman, who has been investigating Trump’s charity.

Trump is no stranger to New York politics, however, and will have former Mayor Rudy Giuliani, one of his closest allies, with him. And he's closer to the Catholic church than Clinton on the key issue of abortion.

Meanwhile, both will have plenty of other targets for roasting, like New York City Mayor Bill de Blasio and Gov. Andrew Cuomo, who may end on the receiving end of jokes they don’t want to level at each other.

But Clinton and Trump will have one other obstacle to navigate: The traditional photo op of the two candidates shaking hands.