Obama’s reemergence on the campaign trail for Harris comes as he recognizes his own legacy is at stake

(CNN) — America and the world have a lot riding on who wins in November. So does Barack Obama.

And that’s part of what is powering what people familiar with Obama’s plans told CNN will be the most active closing weeks of an election the former president’s had since his own last campaign. More rallies are coming every week. This past Wednesday alone, he recorded 21 videos for the Harris campaign. More ads for Democratic Senate candidates are already in the can. Content with influencers will keep popping online. He’ll even be doing a few interviews of his own.

This is on top of a range of meetings and phone calls Obama has held over the last year with Kamala Harris, Joe Biden and other top Democrats, first reported by CNN, as advisers, friends and political allies say the former president has become increasingly alarmed by Donald Trump’s continued hold on the country and its politics.

Obama no longer thinks he can get to the people locked in with Trump.

He’s just hoping to help find enough votes in enough states to counter them.

If the vice president wins, Obama will feel vindicated, and in many ways, will be released to more of the post-presidency he’d been hoping for since right before he called to congratulate Trump on election night 2016 — the first time (and ultimately one of the few times) the two spoke.

But a thought has circulated among several people close to the former president, they told CNN: If Trump wins, Obama might be seen as the aberration in the history of American politics, rather than Trump and his nativist authoritarianism. Obama acolytes have spent the last eight years rationalizing Trump as the last gasp backlash to the Democrat and his presidency.

Obama always wanted to stay involved in politics, just more as an emeritus elder steering what came after him, without as many rallies and constant calls to swoop in and save the party. He would like to see his theory proved true that stepping back wasn’t just about making money off of podcasting with Bruce Springsteen or narrating a documentary series about parks for Netflix — as some resentful Democrats came to feel — but about letting new people emerge without his shadow.

“The goal has always been to pass the torch to the next generation of leaders to ensure the party is sustainable long term without him,” said Hannah Hankins, a spokesperson for the former president who first worked for him in the White House.

All that and the survival of much of what he put in place as president depends on his main mission for the fall: breaking through to  young Black men, as he is uniquely situated to do, hoping they don’t give up on the Democratic Party in the high numbers that even internal Harris-aligned campaign polling show may be happening.

That poured out of Obama on Thursday, when ahead of his first campaign rally in Pittsburgh, he turned what was supposed to be a perfunctory stop by a Harris office into a visceral calling out of young Black men for “coming up with all kinds of reasons and excuses” for not supporting Harris, abandoning their communities and themselves. He said he feared that they are either being fooled by Trump or “you just aren’t feeling the idea of having a woman as president.”

Obama can still draw a crowd. A dozen of the 4,500 people packing a gym on the University of Pittsburgh campus on Thursday night told CNN in interviews that they still feel connected to him — including a 15-year-old named Kai Jones, wearing a T-shirt printed with the famous photo of Obama and Biden jogging through the Rose Garden. Jones, who wasn’t yet born in 2008, said Obama “has a special place in my heart.”

But if the question remains: Can Obama draw in those young Black men? On Thursday in Pittsburgh, there weren’t as many of those faces in the crowd.

“The fact that he has not been in the day-to-day political scene, people don’t see him in the partisan muck that everybody else,” Austin Davis, the Pennsylvania lieutenant governor and a 35-year-old Black man himself, told CNN ahead of the rally. “You have to think about the type of people who naturally show up to political rallies. It’s not just the crowd here, it’s the crowd that’s watching at home.”

Campaign strategy meetings and advice on Washington

Most of the Democratic work Obama has been doing the last few years has been behind the scenes. A lot has been with Hakeem Jeffries, the New York congressman hoping to become the next speaker of the House whose connection to the former president runs so deep that, as he sometimes points out, he has the same birthday and his wife is also named Michelle.

After their own one-on-one meeting, Obama asked Jeffries to suggest a few small groups of Democratic House members for trips to his office in the World Wildlife Federation in northwest Washington. The members ranged from New York Rep. Alexandria Ocasio-Cortez to much lesser known and less progressive up-and-comers, like Washington Rep. Marie Gluesenkamp Perez and Alaska Rep. Mary Peltola. He talked to them about coming off like real people rather than scolding coastal elites and staying consistent rather than being pulled into the whirlwind of Washington consultant advice, according to people in the room.

Several took written notes, including a nervous congressman who watched Obama play with an aide’s child before their meeting started and wrote down to focus on learning how to charm babies, according to one of the people who saw it.

Obama’s session last November with Senate Majority Leader Chuck Schumer and the incumbent Democratic senators running in 2024 was more focused on briefing Obama on their races so he could better understand their challenges and offer support.

“It was great to be able to begin the strategy with him,” said Pennsylvania Sen. Bob Casey, whom Obama has liked since they were in the Senate together and whom the former president insisted be seated onstage to be in the shot with him throughout Thursday’s rally in Pittsburgh.

Casey later came by for his own separate meeting, as did Reps. Elissa Slotkin and Ruben Gallego, the Democratic Senate nominees in Michigan and Arizona. The list goes on and includes Pennsylvania Gov. Josh Shapiro, who stopped by a year before he became an Obama world favorite in this summer’s running mate search for Harris.

Campaigning in Pennsylvania a few hours before heading to Obama’s speech Thursday, though, Arizona Sen. Mark Kelly said he’s ready to step forward and help pull Harris and other Democrats over the line.

Asked whether he was ready to see Obama hold to his theory of turning over to the next generation of Democrats, Kelly said, “Not yet.”

Navigating Biden and coming around on Harris

Obama had hoped to start stepping back when Biden won. Neither president was thrilled with how the last few years played out between them.

Long before Biden’s dismal debate in June, the president had been complaining privately that Obama wasn’t helping enough, according to several people who spoke to Biden. Biden aides sensed a jealousy from Obama’s orbit that they were racking up more accomplishments than he had, with senior adviser Mike Donilon saying once in private conversation, “They need to get over it,” according to one of the people who heard it — and Biden aides hated the Republican conspiracy theory that Obama was actually pulling the strings.

For over a year, when Biden wanted a former president sounding board, he was ringing up Bill Clinton instead.

After Biden’s debate debacle, diehards burned that Obama had left the president to twist in the wind when he could have more forcefully ended the questions, while many Democrats suffering through that month felt he was going feckless again. Many calls came in.

Biden’s dropping out sparked its own Obama drama, and not just because the president’s immediate endorsement of Harris came with the added benefit of demonstrating a deference he often complained he never got from his old boss. While most of the party leaders Harris called that Sunday afternoon, including Bill Clinton, immediately pledged support, Obama held off. He offered advice and encouragement but told her he wanted to make sure the process was seen as legitimate in a way it might not have if he had jumped out early.

Harris advisers knew Obama and former House Speaker Nancy Pelosi favored an open process to find a new nominee. What some couldn’t figure out was how much of that was Obama’s doubts and disappointments about Harris from her 2019 campaign and early vice presidency shining through, and how much was a political calculation that she would be better off if she emerged after a process rather than a coronation.

Several people familiar with Obama’s thinking said that he thought she was in the strongest position starting out, but he believed others would run — and that he was pleased to see her talking that week about earning the nomination even as others didn’t. When the Obamas called Harris that Wednesday to officially endorse, his argument was that he was acting as the closer, certifying party unity, even as some outsiders complained it looked like he had held out as long as he could.

Obama and Biden have spoken once since the president dropped out. Obama initiated the conversation, telling aides to let the White House know he was eager for a call whenever Biden had time, and they soon spoke. It wasn’t the two presidents’ deepest or longest conversation. Obama said he appreciated all that Biden had done as president, and how hard stepping aside was. He said he loved him like a brother and always would. Biden took the call to heart, without hard feelings. He thanked Obama for reaching out.

Obama has had several conversations with Harris, whom he first got to know through an informal network of up-and-coming Black politicians when he was a state senator and she was a district attorney. One centered entirely on her running mate selection, though he was giving his take on how she should approach the process rather than weighing in for one candidate. Others have been to help guide her through everything from staffing decisions to bigger picture strategy. And according to people who know about the conversations, he checks in with several of his own closest aides now helping run Harris’ campaign, such as current campaign chair Jen O’Malley Dillon and his own 2008 campaign manager, David Plouffe.

In both public and in private conversations, Obama has heaped praise on Harris for the way she’s campaigned and what she’s campaigning on.

Meanwhile, conversations are underway to get Michelle Obama to carry through with her own “do something” speech from August’s Democratic National Convention. She’s expected to do an event or two — but not much more than that.

‘He doesn’t feel like history’

Standing in the gym waiting for Obama, Paige Mirsky, a 24-year-old biochemistry graduate student originally from Buffalo, said that part of the reason she was there was because watching his convention speech “made me want to actually do something.”

“He feels like the future,” she said.

She acknowledged that she had been all of 8 when Obama first won, that she hadn’t been steeped in the details of his record in office, and that he has been out of the White House a long time already.

Obama’s leaving office was “a turning point,” Mirsky said. “That was the last time anybody felt normal.”

A few feet over, a 64-year-old physics professor named Eric Swanson who had grown up in Canada before becoming a US citizen said that watching Obama in Grant Park on election night 2008 was “the only time I felt proud to be an American.”

He said he’s hoping to feel that same feeling with Harris. He doesn’t feel it yet. Maybe, Swanson said, Obama would get him there.

A clump of Pitt freshmen found spots in the middle of the floor, waving to friends and making sure they’d still have the sight lines right to the man himself.

“My parents talk about him a lot,” Amelia Staresink said, explaining why she felt connected to a president who had left office when they were in fourth grade.

“He doesn’t feel like history,” said Sara Kulkarni.

With as much as they feel like they keep seeing him, “it’s an active history,” Eve Majewski said.

In the 2022 midterms, Obama’s decision to rip into Republicans as a threat to Social Security pushed the topic into a main talking point for Democrats in the final stretch. With the energy around Harris flagging, the prods he debuted in Pittsburgh go far beyond how he called out young Black men: viciously mocking Trump as an out-of-touch and self-centered whiner, tearing into Trump’s claims of credit for managing a good economy, then finishing with a long “Why would we go along with this?” section about Trump’s division and disinformation that betrayed Obama’s deep frustration with the Republican nominee’s hold on America.

Onstage, Obama was riffing so much that he picked up a shoutout from the crowd about Trump wearing a diaper.

“I almost said it, but I decided I should not say it,” he said with a big smile and shake of his head.

When Obama feels like a speech has caught the way he wanted it to, he smacks the side of the lectern. Sometimes twice, a fast double tap.

Thursday night, when he finished in Pittsburgh, he backed up from the microphone for a moment without doing it. Then he stepped forward again and brought his hand down hard, right in the center.

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