NEW YORK — It was bound to be awkward from the beginning.
On a night in which Donald Trump and Hillary Clinton would meet for perhaps the final time, the staging called for the two presidential candidates to be separated by a man of God.
The choreography at the Alfred E. Smith charity dinner benefitting the Catholic Church's charities — an annual New York tradition for the city's well-heeled and a quadrennial circus when the presidential candidates come to town — was perfectly set.
Melania Trump entered first and took her seat. Clinton, in a floor length fuchsia ball gown, entered next, moving deftly behind her to take a chair a few feet away, with nothing more than a polite greeting.
As Trump took the stage in white tie, he flashed a thumbs up and a wave, shaking hands with those on stage but seeming to make no acknowledgement of Clinton's existence. He fidgeted throughout the opening formalities, tugging at his formal suit coat, thumping his fingers as they were placed over his heart during the national anthem and swaying during a prayer that begged God for an end to this election.
As the dinner's chairman rattled off one joke after another - nearly all of which poked fun at Trump - the Republican nominee mostly smirked, while Clinton often threw back her head and laughed. Through it all, Trump's wife sat back, stonefaced, as if steeling herself for the inevitability of a night of barbs to come.
Trump's turn came first. He sauntered to the podium and planted his finger on his paper, reading the words haltingly.
"You always start out with a self ... deprecating joke," Trump said. The crowd chuckled. "Some people think this will be tough for me, but the truth is I'm actually a modest person. Very modest. It's true."
The crowd shuffled anxiously, but Trump kept on. He joked about Melania plagiarizing first lady Michelle Obama and about Clinton's small crowds.
"This is corny stuff," Trump remarked, bored with the mild mannered nature of the jokes written for him.
Normally the fundraising dinner — which this year had raised more than $6 million — is a night in which politics is not so much put aside as deployed in service of a greater good, namely good-natured humor and charity. And Trump seemed off to a good start. But soon, as things often do for the Republican nominee, his fortunes went south quickly.
Jokes that seemed better placed at his roiling and adoring rallies set the heavily Clinton-leaning crowd on edge.
"Hillary is so corrupt she got kicked off the Watergate commission," Trump declared.
"Booooo!" the agitated crowd called back. Behind him, the face of former ambassador Elizabeth Frawley Bagley was tense and set.
"All of the jokes were given to her in advance of the dinner by Donna Brazile," Trump said, referring to the acting Democratic National Committee chairwoman. Boooooo!
"Here she is in public pretending not to hate Catholics!"
More boos and jeers.
Clinton was no longer laughing, let alone smiling, and Cardinal Timothy Dolan, the Archbishop of New York and the night's mediator between the two candidates, leaned over, engaging her in conversation as Trump kept going.
The crowd was fed up. But there was no going back, and Trump knew it. He carried on until he reached the customary closing of his speech, a call for togetherness and respect for the sanctity of life that were received with, at most, polite applause.
Trump had walked on the wire and quickly lost his balance. He had missed the tone and lost an already frosty room with overtly political jabs.
He took his seat and Clinton seemed unfazed smiling widely. Dolan wiped his brow.
"As Ronald Reagan would say, there you go again!" deadpanned Smith before he introduced Clinton, who nearly got the crowd to its feet without uttering a word.
But the outcome wasn't far from what virtually everyone expected.
Their last meeting in Las Vegas may not their most contentious — that would be reserved for the second debate which featured a parade of women who had accused former President Bill Clinton of sexual misconduct — but it was pretty close. And the bitter and nasty tenor of the presidential race had promised to make this event either a triumph of both candidates' speech writers who could joke their way through the tension or a grippingly awkward affair.
It was the latter.
Just hours ago, Trump dismissed Clinton as a "nasty woman" and Clinton criticized Trump for belittling women who had accused him of sexual misconduct.
In past years, the policy disputes made decent fodder for jokes and it wasn't a stretch for the candidates to put those differences aside. Politicians have used this as an opportunity to not only prove that they have a sense of humor but that they can also make fun of themselves, turning gaffes into punchlines. There are often political jabs thrown, but softened with sarcasm.
In 2008, John McCain joked about "Joe the Plumber" and his own inability to remember how many houses he owned, saying: "Joe the Plumber recently signed a very lucrative contract with a wealthy couple to handle all the work on all seven of their houses." Barack Obama, then a senator, deadpanned: "My middle name is actually Steve. Barack Steve Obama." Both took time to compliment one another.
In 2012, Republican Nominee Mitt Romney made a point to praise President Obama, for his positive qualities.
"It would be easy to let a healthy competition give way to the personal and the petty but fortunately, we don't carry the burden of disliking one another," Romney said.
This year, it was different. Clinton took shot after shot at Trump.
"If you don't like what I'm saying, feel free to stand up and yell "wrong!" Clinton told him, foreshadowing the next few minutes.
The joked that Trump would rate the Statue of Liberty as a "four" on a scale of 1 to 10, or maybe a "five" if she ditched the torch and tablet and changed her hair. She needled him for losing the support of Republicans, suggested that he wasn't a billionaire, and being egger to get into Twitter wars with celebrities.
Clinton also aimed for self-deprecating a few times, but seemed to miss the mark, sounding more congratulatory.
"I am so flattered that Donald thought I was using a performance enhancer," Clinton said of the debates. "Well actually I did, it's called preparation."
Meanwhile, Trump smiled at some of the jokes but didn't laugh like Clinton had. When she made a crack about Trump struggling to translate Russian off his teleprompter, he rocked side to side in his seat.
Of the two denizens of New York, Clinton was clearly the favorite and she played to the crowd easily.
"There are a lot of friendly faces here in this room," Clinton said smiling broadly. "I just want to put you all in a basket in adorables!"
They reciprocated with a round of louder and warmer applause than they had spared for Trump.
When she was finished, Dolan rose from his seat between the two candidates, which he quipped was the "the iciest place on the planet," to offer another much-needed prayer.
Trump leaned over, attempting to congratulate Clinton who had her back turned to him initially. Eventually, she turned and the two finally shook hands under the table.
For that, the night's emcee offered one suggestion: "I think we should nominate Cardinal Dolan for the Nobel Peace Prize."