Picture this: a White House reeling from an electoral earthquake in 2016, with staffers fighting back tears as they hand over the keys to a man they’d warned was a risk to the nation.
Josh Earnest, who served as Barack Obama’s press secretary from 2014 to 2017, recently unpacked this tumultuous chapter at the 2025 National Association of Hispanic Journalists conference in Chicago, revealing the raw emotion and logistical tightrope-walking that defined the Obama administration’s final days after Donald Trump’s unexpected win, The Guardian reported.
Earnest didn’t mince words about the 2016 election aftermath, calling it the hardest period of his tenure in the White House.
Before the votes were even tallied, the Obama team had sounded alarms about what Trump’s leadership might mean for America, painting a grim picture of potential consequences.
“About what could or would happen,” Earnest recalled of those dire predictions, and yet, when the results rolled in, he admitted, “I was very surprised.” Surprised? That’s an understatement when your worst-case scenario walks into the Oval Office.
Intelligence reports at the time pointed to Russian interference in the election that saw Trump defeat Hillary Clinton, a bitter pill for the administration to swallow while still pledging a peaceful transfer of power.
Earnest and his colleagues were grilled by journalists on whether Obama genuinely believed Trump posed a danger, with questions like, “Did he not mean how dangerous?” echoing through briefings. It’s the kind of scrutiny that stings when you’re already down, but Earnest took it on the chin.
Behind closed doors, the mood was grim—many communications staffers were visibly demoralized, and Earnest himself described them as “emotional” that fateful morning. Turns out, losing an election you didn’t see coming can hit harder than a freight train.
To rally the troops, Earnest gathered the staff to refocus for the final stretch of Obama’s term, while the president himself called a meeting in the Oval Office to preview a Rose Garden speech alongside Vice President Joe Biden.
For many staffers, it was their first time stepping into that iconic room during this crisis moment, a poignant scene captured by official photographer Pete Souza. “It was very poignant,” Earnest noted, and you can almost feel the weight of history in that frame.
Obama’s words in the Oval Office carried a unifying tone: “We have to remember that we’re actually all on one team.” It’s a noble sentiment, though some might argue it’s tough to sing Kumbaya when you’re handing over nuclear codes to a man you’ve called a risk.
Even as the administration worked through logistics for Obama’s televised address, the sting of Trump’s victory lingered, with Earnest admitting the message was “tough” to deliver under such circumstances.
Trump, never one to shy away from a fight, aimed Earnest during a December 2016 rally after the press secretary defended intelligence assessments on Russian meddling, branding him a “foolish guy” who was “so bad” at delivering messages. Well, if you can’t take the heat, don’t stand at the podium—Trump’s jab was sharp, but Earnest had already weathered worse storms.
Post-White House, Earnest briefly dipped into media punditry during Trump’s early presidency, only to find it less than “particularly fulfilling” due to the chaotic, unpredictable style of governance that left newsrooms scrambling. “Isn’t this outrageous?” became the daily refrain, and Earnest grew weary of just saying, “Yes,” in different flavors.
Since 2018, he’s shifted gears to a top spokesperson role at United Airlines in Chicago, a move away from the political circus and into steadier skies. If nothing else, it proves there’s life after the White House—even if the ghosts of 2016 still haunt. And perhaps a lesson for all: sometimes, the warnings you give are the realities you face.
