Obama's Return to the Campaign Trail for Harris Signifies His Recognition of Possible Impact on His Own Legacy
And that's part of what's fueling what insiders in Obama's circle told CNN will be the most active final weeks of an election for Obama since his own last campaign. More rallies are scheduled each week. On Wednesdays alone, he's been recording 21 videos for the Harris campaign. More ads for Democratic Senate candidates are ready. Content featuring influencers will keep popping up online. He's even planning some interviews of his own.
Over the past year, Obama has held numerous meetings and conversations with Harris, Biden, and other top Democrats, as revealed earlier by CNN. Advisers, friends, and political allies said Obama has grown increasingly concerned about Trump's continued hold on the country and its politics.
Obama no longer believes he can reach people locked in with Trump.
He's just hoping to help gather enough votes in enough states to counteract them.
If Harris wins, Obama will feel validated, and in many ways, he'll be able to move forward with the post-presidency he'd been hoping for since just before he congratulated Trump on election night 2016—the first and, unfortunately, one of the few times they spoke.
A theory has been circulating among those close to Obama: If Trump wins, Obama might be seen as an anomaly in American politics, rather than Trump and his nativist authoritarianism. Obama supporters have been explaining Trump as a backlash akin to Obama's presidency for the past eight years.
Obama wanted to remain involved in politics, but more as an emeritus elder guiding the future without as many rallies and constant interventions island-saving the party. He'd like to see his theory proven right: that stepping back wasn't just about earning money from podcasting with Bruce Springsteen or narrating a series about parks for Netflix—as some Democrats grew disgruntled about—but about creating opportunities for fresh faces without the weight of his shadow.
According to Hannah Hankins, a spokesperson for the former president, Hankins initially worked for him in the White House, "The goal has always been to pass the torch to the next generation of leaders to ensure the party's sustainability in the long term without him."
Much of what he accomplished during his presidency depends on his primary mission for the fall: connecting with young Black men, who, he feels, might abandon the Democratic Party in high numbers, as even Harris campaign polling indicates.
Those feelings poured out of Obama during his visit to a Harris campaign office in Pittsburgh on Thursday. He chided young Black men for creating excuses to not support Harris, deserting their communities, and potentially being deceived by Trump or simply unenthused about a female president.
Obama still has the power to attract a crowd. Approximately 12 of the 4,500 people crammed into a gym at the University of Pittsburgh on Thursday expressed their continued affection for him—even a 15-year-old named Kai Jones, adorned in a T-shirt emblazoned with the famous photo of Obama and Biden jogging through the Rose Garden. Jones, who wasn't born in 2008, said Obama holds a special place in his heart.
But if the query remains, can Obama draw in those young Black men? In Pittsburgh on Thursday, those faces were less prominent in the crowd.
"The fact that he's been out of the political spotlight makes people less likely to see him as partisan muck," Texas lieutenant governor and 35-year-old Black man Austin Davis told CNN before the rally. "You have to consider the type of people who usually attend political rallies. It's not just about the crowd here." "It's about the crowd watching at home."
Campaign strategy sessions and advice on Washington
Most of the Democratic work Obama has done in recent years has been done quietly. A significant amount of it has been with Hakeem Jeffries, the New York congressman who dreams of becoming the next House speaker, whose connection to the former president is so profound that he shares the same birthday and has a spouse named Michelle.
After their one-on-one meeting, Obama asked Jeffries to suggest several small groups of Democratic House members for meetings at his office in northwest Washington. The members involved ranged from New York's AOC to less well-known and less progressive rising stars, like Washington's Marie Gluesenkamp Perez and Alaska's Mary Peltola. He spoke to them about seeming genuine instead of condescending and resisting the influence of Washington consultants, according to sources in the room.
Several took notes, including a nervous congressman who observed Obama playing with an aide's child before their meeting began and jotted down, "Focus on mastering baby charm methods." This was confirmed by one of the witnesses in the room.
"It was cool to get things started with him," mentioned Pennsylvania Sen. Bob Casey, who Obama has liked since they were both in the Senate and who Obama insisted be present during the entire rally in Pittsburgh's Thursday event.
Later, Casey, along with Reps. Elissa Slotkin and Ruben Gallego, the Democratic Senate candidates in Michigan and Arizona, respectively, showed up for separate meetings. The list goes on and includes Pennsylvania Gov. Josh Shapiro, who paid a visit a year earlier when he became a favorite of Obama during this summer's vice president search for Harris.
Campaigning in Pennsylvania prior to Obama's speech on Thursday, Arizona Sen. Mark Kelly expressed his readiness to help get Harris and other Democrats over the line.
When asked whether he was prepared for Obama to hand over the reins to the next generation of Democrats, Kelly replied, "Not yet."
Navigating Biden and embracing Harris
Obama had hoped to begin stepping back once Biden won. Neither president was happy with how the past few years had unfolded between them.
Before Biden's poor debate performance in June, the president had been voicing his displeasure in private about Obama not providing enough support, according to several who had spoken to Biden. Biden's aides perceived a jealousy from Obama's circle that they were achieving more accomplishments than he had, with senior advisor Mike Donilon once saying in a private conversation, "They need to get over it," as reported by one who heard it – and Biden's aides despised the Republican conspiracy theory that Obama was really pulling the strings.
For over a year, whenever Biden needed an ex-president sounding board, he would dial up Bill Clinton instead.
Following Biden's debate blunder, critics accused Obama of abandoning him while he struggled, while many Democrats who endured that difficult month felt he was once again showing signs of weakness. Many calls were made.
Biden's withdrawal sparked its own Obama drama, and not just because of the immediate endorsement he gave to Harris, which signified a deference he often complained he never received from his old boss. While most party leaders Harris contacted that Sunday afternoon, including Bill Clinton, offered their immediate support, Obama waited. He provided advice and encouragement but indicated he wanted to ensure the process appeared legitimate, as it might not have if he had jumped in early.
Harris' advisors understood that Obama and former House Speaker Nancy Pelosi preferred an open process to find a new nominee. However, they struggled to decipher whether this stemmed from Obama's doubts and disappointments in Harris from her 2019 campaign and early vice presidency, or if it was a political calculation aimed at benefitting her by her emerging from the process instead of being crowned.
Several familiar with Obama's thoughts stated that he believed Harris started with a strong position, but he anticipated others would enter the race – and he was pleased to see her discussing earning the nomination even as others didn't. When the Obamas called Harris that Wednesday to offer their official endorsement, his argument was that he was serving as the closer, sealing party unity, even as some outside criticized it as appearing like he had held off as long as he could.
Obama and Biden have communicated only once since Biden dropped out. Obama initiated the contact, informing Biden's team that he was eager for a chat whenever Biden had time, and soon, they spoke. It wasn't a lengthy or deep conversation. Obama expressed his appreciation for all that Biden had done as president and the difficulty of stepping aside. He said he loved him like a brother and always would. Biden took the call to heart, with no hard feelings. He thanked Obama for reaching out.
Obama has had regular conversations with Harris, whom he first interacted with through an informal network of rising Black politicians when he was a state senator and she was a district attorney. One conversation centered entirely on Harris' running mate selection, but rather than recommending a particular candidate, he offered his perspective on how she should approach the process. Others have been to help guide her through team selections and broader strategy. And as reported by those familiar with the conversations, he frequently touches base with several of his own closest advisors now overseeing Harris' campaign, such as current campaign chair Jen O'Malley Dillon and his own 2008 campaign manager, David Plouffe.
In both public and private conversations, Obama has commended Harris for her campaign approach and the issues on which she is campaigning.
Meanwhile, discussions are underway to have Michelle Obama carry out "her own 'do something' speech" from August's Democratic National Convention. She's expected to participate in 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 from Buffalo, stated that one reason she was there was because watching his convention speech ignited her desire to act.
"He feels like the future," she said.
She acknowledged that she had been just 8 during Obama's first election, that she hadn't delved into the intricacies of his administration's record, and that he had been out of office for quite some time already.
Obama's departure from office was "a turning point," Mirsky said. "That was the last time anyone felt normal."
A few feet away, a 64-year-old physics professor named Eric Swanson, who emigrated from Canada before becoming an American citizen, shared that watching Obama in Grant Park on election night 2008 was "the only time I felt proud to be an American."
He expresses his hope to replicate that same emotional connection with Harris. However, he hasn't experienced it yet. According to Swanson, Obama might be the one to help him achieve that.
A group of freshmen from the University of Pittsburgh claimed some prime spots in the middle, eagerly waving to acquaintances and maintaining unobstructed views of the main attraction.
"My parents often discuss him," Amelia Staresink explained, highlighting her attachment to a president who had already left office when they were in the fourth grade.
"He doesn't feel like history yet," stated Sara Kulkarni.
Despite how frequently they believe they encounter him, "it's an active history," Eve Majewski asserted.
During the 2022 midterms, Obama's criticism of Republicans as a threat to Social Security became a significant talking point for Democrats, gaining traction in the closing stages. With the excitement surrounding Harris beginning to wane, the harsh remarks he made in Pittsburgh went beyond just his criticism of young Black men; he viciously ridiculed Trump as an out-of-touch, self-centered complainer, challenged Trump's claims of economic success, and concluded with a passionate segment criticizing Trump's divisive nature and spread of false information, revealing Obama's evident frustration with Trump's grip on America.
Onstage, Obama was so engrossed in his speech that he nearly responded to the crowd's shoutout about Trump wearing a diaper.
"I almost said it, but I decided it wouldn't be appropriate," he smiled, shaking his head.
When Obama feels that a speech has been delivered to his satisfaction, he typically slaps the side of the lectern. On this particular night in Pittsburgh, he refrained from doing so upon finishing, only to approach the microphone again and deliver a powerful, central strike.
Obama has expressed concern about Trump's continued hold on the country and its politics, believing that Trump's authoritarianism might overshadow him in American politics if Trump wins the election. Obama wants to stay involved in politics, but he prefers to guide the future from the sidelines, allowing new leaders to emerge without his shadow looming over them.
