Shuttling between two sets of offices on the 14th floor of Trump Tower as afternoon turned to evening on Nov. 8, Election Day, one thought was nagging at the back of Jay Connaughton’s mind:
“What are we missing? What are others seeing that we are not?”
Connaughton, a media adviser with the Donald Trump campaign, knew that the campaign’s numbers painted an optimistic picture. But media reports indicated that a Hillary Clinton victory was all but assured.
And now there was nothing to do but wait.
“In our business, Election Day is the worst day because you have no control,” Connaughton said.
As the day wore on, Connaughton and others on Trump’s team moved between the war room, where a wall of TVs monitored the news channels, and a separate set of offices where the campaign’s data crunchers were getting vote totals and running models.
The models looked good.
At first glance, Connaughton may seem an unlikely person to be near the beating heart of one of the most turbulent presidential elections in modern American history. Short and stout, his home office is in a nondescript strip mall on La. 22 in Mandeville. His firm isn’t even that big — just 30 full-time employees. In other words, he’s not a K Street or a Madison Avenue behemoth.
Connaughton and his wife founded the firm, Innovative Advertising, in the late 1990s. They do corporate advertising for companies as diverse as Abita Beer and Chevron — work they try to keep separate from the political side of their business.
“Politics is much more personal,” Connaughton said. The company has tried to stay away from local elections, he said, but he did assist Brian Trainor’s losing 2014 bid for district attorney in St. Tammany Parish. The company has worked in more than a dozen Senate races around the country and congressional races in eight states.
Working on a presidential race was something else.
“This is the Super Bowl,” Connaughton said.
Connaughton was brought into the race by Trump’s campaign manager, Kellyanne Conway. He had worked with Conway on education initiatives through Americans for Prosperity, a conservative advocacy group.
“We really clicked with the way she operates,” Connaughton said. “We developed great rapport."
For her part, Conway was glad to get Connaughton on board. “He’s very creative and high-energy,” she said.
That energy was key: When Connaughton pitched his services to the Trump campaign after the Republican National Convention, he was hired on the spot. He then went on the road for 3½ weeks.
Trump’s campaign operated differently from others, not just in tone and approach, but also in size and money, Conway said. “We had a fraction of the money and personnel that Hillary Clinton had,” she said.
For Connaughton, the smaller team was an opportunity. Instead of the five or six media advisers one might find on a normal presidential campaign, Trump’s team had three.
He was able to do things beyond just shooting ads. He helped organize Trump’s post-flood trip to Baton Rouge, where for a few moments, the candidate helped distribute supplies to flood victims.
He also accompanied Trump to Flint, Michigan, site of a contaminated water crisis. Trump “was touched” by what he saw there, Connaughton said.
But his main focus was on producing television ads, including one called “Listening,” in which a working mother talks about her economic struggles. Another, called "United," aired during the last week of the campaign, featuring sweeping footage from a Trump rally.
Interestingly, Connaughton said, voters responded more favorably to hearing other voters talk about their lives, and less than a fifth of the ads produced by Trump’s team featured Trump’s voice.
In all, Connaughton produced about 30 ads for the campaign, about eight of which were aired.
All that led up to the last weeks of the campaign, when Connaughton was wondering why national media weren’t reporting the same things the Trump team was seeing.
“We were looking at the data points,” he said. “We said, 'This looks like a victory to us.' ”
Connaughton noted that Trump was out-polling 2012 GOP candidate Mitt Romney in key areas and that the early voting numbers seemed to be favorable for a Trump win.
“We kept running different models,” he said, trying to figure out what scenarios could play out.
On election night, Connaughton returned to the Trump Tower war room. About 9 p.m., the candidate walked in along with his running mate, Mike Pence.
“It was really surreal,” Connaughton said.
A photo from that night that Connaughton posted to Facebook shows him and his wife in the foreground, a few feet away from Trump, who is staring intently at the screens in front of him.
“We were all surprised when he came in there,” Connaughton recalled. “He wanted (the TV) on CNN, and he wanted it loud enough to hear what they were saying.”
Trump took some phone calls, thanked the workers for their work, and then there was an announcement.
All the workers who wanted to get to the election night party needed to leave, they were told. Trump had a motorcade to the Hilton Hotel a few blocks away, but Connaughton and others would have to walk, navigating through crowds of protesters and security.
“We knew when we left Trump Tower at 10:30,” he said about a Trump victory. “We knew based on our data.”
Since then, it’s been a whirlwind, though Connaughton said he was taking Thanksgiving week off to be with his family. But he’s excited about the future.
“We’ve been told we will have some role in the administration,” he said. “We are thinking forward to post-inauguration.”