Obama’s fears about Trump drive his stepped-up campaigning

In the early spring, former president Barack Obama joked to some allies that his blood pressure was finally going down — because he had stopped watching cable news.

After spending much of the previous two years deeply concerned about the prospect of Donald Trump returning to the White House, Obama told people that his lifestyle change had helped calm his nerves, according to multiple people familiar with his comments, who spoke on the condition of anonymity to discuss private conversations.

But that was before President Joe Biden’s rocky debate with Trump in June and the ensuing intraparty war over whether the president could win a second term, when Obama’s concerns soared again. He was once again deeply worried, privately warning allies that Biden needed to seriously consider the viability of his candidacy because of the seriousness of Trump’s candidacy.

Now polls show Trump and Vice President Kamala Harris locked in a tight race, renewing apprehensions among Democrats throughout the country — few more so than Obama, whom some jokingly call the party’s biggest bed-wetter.

With just over two weeks until Election Day, Obama is now crisscrossing the country on behalf of Harris, unleashing his frustration about Trump while exhorting voters and at times admonishing them, to turn out for Harris. Over the next five days, Obama will appear at rallies in four battleground states, beginning Friday in Tucson and Saturday in Las Vegas. On Tuesday, the former president will appear in Detroit and in Madison, Wis.

Obama will make his first joint campaign appearance with Harris in Georgia on Thursday. Next Saturday, Harris will campaign with former first lady Michelle Obama, who will be making her first appearance on the campaign trail since delivering one of the best-received speeches at the Democratic National Convention.

Despite leaving office eight years ago, Barack Obama, 63, remains among the most popular figures in the Democratic Party. A charismatic, still-youthful figure despite his graying hair, he represents to many Democrats their party’s role in breaking racial barriers, and his record seems proof that an eloquent liberal can win hard-fought presidential races.

Harris’s aides are eager to deploy the former president in the final weeks to help with their get-out-the-vote efforts, planning some of his rallies to coincide with the first day of early voting in several battleground states.

Former Obama aides say the rallies are also cathartic for the former president, as he is able to freely speak about the deep fear he holds about another Trump presidency and express the disdain and anger he feels about how Trump has undermined democracy. A spokesperson for Obama declined to comment.

At his first rally for Harris last week in Pittsburgh, Obama skewered Trump, at times mocking the former president while also delivering a stark warning about the dangers of reelecting him.

“There is absolutely no evidence that this man thinks about anybody but himself,” Obama said. “I’ve said it before: Donald Trump is a 78-year-old billionaire who has not stopped whining about his problems since he rode down his golden escalator nine years ago.”

David Axelrod, a former top aide to Obama, said Obama’s plan when he left office was to remain relatively quiet about his successor but that he grew so alarmed during Trump’s term that he felt he could no longer remain silent.

“Obama has been pretty direct, in public and private, about his concerns about Trump, and it’s not about his own legacy but about the underpinnings of our democracy,” Axelrod said, adding, “What made his remarks last week so powerful was how deeply felt his words and utter contempt for Trump were.”

Obama has in a sense been wrestling with Trump’s impact since the real estate magnate broke onto the political stage in 2015. Trump’s victory the next year, defeating Obama’s secretary of state, Hillary Clinton, was seen by many as a rebuke of Obama’s presidency. When Biden, Obama’s vice president, then ousted Trump in 2020, it provided Obama a measure of vindication.

Now, as Trump seeks a return to the White House and faces off against Harris, a longtime Obama ally who would be the second person of color to occupy the White House, associates say Obama feels deeply invested in the outcome, believing it could deliver a final verdict on his own legacy.

Since Trump announced he was running for a second term, shortly after the 2022 midterm elections, Obama has been deeply concerned about the Republican’s political strength, warning friends and allies in private — including Biden.

In June 2023, Obama visited the White House for a private lunch with Biden to share his fears. Citing Trump’s intensely loyal following, a sprawling Trump-friendly media ecosystem and a polarized country, he warned Biden that Trump was a more formidable candidate than many Democrats realized at the time.

That same day, Obama filmed a digital fundraising video with Biden, marking his first involvement in the presidential campaign. Since then, Obama has helped raise more than $80 million for the campaign, according to his aides. He also delivered a prime-time address at the Democratic National Convention, after which he called Harris to tell her he was impressed by her performance.

Just before the end of 2023, Obama returned to the White House bearing more specific concerns, citing the structure of Biden’s reelection campaign and the lack of decision-makers at its headquarters in Wilmington, Del. He advised Biden to bring in senior strategists from the White House or outside to turbocharge the battle against Trump. Shortly after that meeting, Jen O’Malley Dillon left the White House and moved to Delaware as Biden’s campaign chair.

Now, as the election grows closer, Obama is showing his frustration more publicly — and drawing some criticism for it. Before delivering his fiery speech in Pittsburgh this month, Obama stopped at a campaign field office where he said he wanted to “speak some truths” and address Black men specifically.

“My understanding, based on reports I’m getting from campaigns and communities, is that we have not yet seen the same kinds of energy and turnout in all quarters of our neighborhoods and communities as we saw when I was running,” Obama said, adding that it “seems to be more pronounced with the brothers.”

The former president then asked how any Black men could be undecided on whom to support, given Trump’s racist comments and his policies that Obama said hurt Black Americans. He directly addressed what he thought could be contributing to Harris’s soft support among some Black men: discomfort with electing the first female president.

“And you’re coming up with all kinds of reasons and excuses, I’ve got a problem with that,” Obama said. “Because part of it makes me think — and I’m speaking to men directly — part of it makes me think that, well, you just aren’t feeling the idea of having a woman as president, and you’re coming up with other alternatives and other reasons for that.”

Obama was channeling Democratic concerns that Harris is showing signs of underperforming among Black men, which could imperil her chances of winning battleground states across the Midwest. Cliff Albright, the co-founder of Black Voters Matter, an organization focused on mobilizing Black voters, said the focus on Black men is needed, but he suggested Obama’s tone was overly harsh.

“His remarks were necessary and the topic is important, but I think the way it was offered could have been better and a little more balanced,” Albright said.

Obama and others often fail to acknowledge that a baseline of close to 80 percent of Black men support Harris, he added, far more than most groups.

“This isn’t about the sensitivities or ego of Black men,” Albright said. “This is standard practice. When you offer critique, there’s a theory. You start with what’s going well, and then you get to the critique, and then you come back with something affirming.”

Joel Payne, a Democratic strategist, disagreed, likening Obama’s comments to “having a tough family conversation.”

“If you’re going to be offended by that, that outreach wasn’t for you,” Payne said. “For a lot of voters who are looking for folks to help them make sense of their choices and what Harris brings to the table and the possibility of a second Trump presidency, I don’t think there’s much of a risk there.”

Payne said Obama is a “highly trusted messenger” for Democrats, particularly Black men, and the Harris campaign is right to use him in the final stretch.

“If there’s any languishing concern about enthusiasm, injecting Obama — and not just Barack Obama — is a good solve for that,” he said, referring to Obama’s wife Michelle.