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The hardest day on the job for the White House press secretary for most of Barack Obama’s second term was right after Donald Trump was first elected president, he recently revealed during a fireside chat at a journalism convention.

Speaking at the 2025 National Association of Hispanic Journalists (NAHJ) conference in Chicago, Josh Earnest said it was grueling for the Obama administration to realize it would have to follow through on promises of a peaceful transfer of power despite spending the 2016 election cycle offering dire warnings “about what could or would happen if Donald Trump were given the keys to the Oval Office”.

Those warnings stemmed in part from intelligence assessments that the US’s longtime geopolitical adversary Russia had interfered in the race in which Trump defeated former secretary of state Hillary Clinton. Earnest said the Obama administration suddenly found itself needing to defend the validity of those assessments while saying it would peacefully transfer over the nuclear launch codes – and other levers of power – to Trump.

“Did [Obama] not mean how dangerous [Trump] could be?” Earnest asked rhetorically, referring to some of the questions he and fellow administration officials faced while briefing journalists at the time. “It was a tough message.”

The remarks on Wednesday from Earnest – who was Obama’s press secretary from 2014 to 2017 – also offered a first-hand peek into the somber mood at the White House after Trump defeated Clinton. Like many, Earnest “was very surprised”. “I did not think he was going to win,” he said.

Many Obama communications staffers were visibly demoralized, and Earnest said he and his aides decided to convene them, talk about Trump’s victory and try to refocus them for the final two months in office.

During that conversation, Obama summoned Earnest to go over the logistics of a nationally televised speech he was planning to give in the White House’s Rose Garden. Earnest recalled Obama asking how it was going with the staff that morning – to which he replied that they were “emotional”.

Obama then asked an assistant to call the staff into the Oval Office. He stood in front of the Resolute Desk near his vice-president, Joe Biden, who would later succeed Trump in the White House – and gave them an early version of the speech he ultimately delivered that day.

“We have to remember that we’re actually all on one team,” part of that speech read. “We are Americans first. We’re patriots first. We all want what’s best for this country.”

As Earnest noted, Obama’s official White House photographer, Pete Souza, captured the scene with his camera. He recalled how it was the first time many people in the room that day had been in the Oval Office.

“It was very poignant,” Earnest told the chat’s host, the ABC7 Chicago news anchor Tanja Babich.

One of Earnest’s most vocal critics in the aftermath of Trump’s victory was the president-elect himself. Trump called Earnest a “foolish guy” at a December 2016 rally.

“He is so bad – the way he delivers a message,” Trump said of Earnest after the latter defended the US intelligence community’s assessment of Russia’s interference.

Earnest has been a top spokesperson for United Airlines at the company’s Chicago headquarters since 2018. He spent some time being a media pundit early during the first of Trump’s two presidencies. But Earnest told Babich he did not find it “particularly fulfilling” given the way Trump’s unpredictable, chaotic style of governing can often disorient news outlets.

“The questions could all be boiled down to, ‘Isn’t this outrageous what Trump is doing?” Earnest said. “And it became about finding different ways to say, ‘Yes.’

“I wasn’t doing journalism. I was doing commentary. And it was pretty close to entertainment.”