The Long Alliance, page 36
In Wilmington and Virginia, he was still acting like a candidate-to-be, discussing donor outreach and possible endorsers, and also spending far more time than was rational making policy plans—on taxes, health care, and Russia, among other topics—for a campaign that clearly wouldn’t be fought along wonky lines. In private he talked so much like he thought he was already president that aides had to specifically make sure he knew he couldn’t slip and accidentally mention a campaign in public, since that would ruin their rollout plans and trigger the legal process formally declaring his candidacy. But at the end of some hours-long policy-focused sessions in McLean, Schultz and Bedingfield would still stand in the driveway and wonder aloud: What did that meeting mean? Had he fully decided to run yet?
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From the perspective of an innocent liberal bystander, it might have been reasonable to assume at this point that a restoration was on deck—that the theoretically thriving political partnership that had been in power for eight years would return and fulfill its natural conclusion to save the country from Trump. Now, perhaps, was the moment where Obama could step in and take Biden arm in arm back to the White House, the retired inspirer emerging to vouch for the old romantic promising to calm the waters and heal the nation’s wounds. The reality, however, wasn’t just less fantastic but almost surgical in its choreographed distance, all thanks to Obama.
Biden, of course, wasn’t alone. By late 2018 the list of Democrats who were thinking about running for president at least somewhat seriously—either out of a real conviction that they could win or a more casual “If Trump can do it, so can I” attitude—stretched beyond four dozen, by far the largest field of potential candidates in modern American history. Considering Obama’s pledge to empower a new generation of leaders post–White House, he couldn’t exactly regard this as a bad thing, even if the primary looked like it might devolve into chaos if the roster of contenders—which ranged from governors to mayors to TV lawyers to bored billionaires—didn’t edit itself down a bit. Still, with little interest in playing a determinative role at this stage in the prerace but also feeling a lingering urge not to exit the game entirely, Obama offered himself up as a consultant to the Democrats considering a run. He made it known via whispered word of mouth that he’d be willing to meet and offer some advice on running a campaign in his West End office for a session that some started calling “the pilgrimage” and a younger cohort compared to “office hours” with a professor.
Neither Obama nor his remaining staff, spearheaded by political and comms advisor Eric Schultz, ever reached out to any of the candidates directly, figuring that if they were serious they would know how to find him. They recognized the precarity of these meetings—Obama knew his every utterance was being dissected and that any leaks or misconstrued comments could dramatically change the primary’s direction—so before the visitors arrived, Schultz or one of his deputies would warn their staff that they were not to say a word about the sessions. When the Democrats would then get to the building, they’d usually sit on the sofa in Obama’s inner office for around an hour, more if it was going well, and pick his brain from across the coffee table. He usually started with the same shtick, whether he knew his visitor or not. He’d caution them not to run unless they thought they could win, urge them to consider what a campaign could do to their family, and counsel them solemnly that they refrain from going any further if they didn’t think they were the best person to be president in the first place. Thus came and went a steady stream of senators—Kamala Harris, Michael Bennet, Elizabeth Warren, Bernie Sanders, Cory Booker, Kirsten Gillibrand, Jeff Merkley, Amy Klobuchar, to name a few—governors—Jay Inslee, John Hickenlooper, Steve Bullock—mayors—Eric Garcetti, Mitch Landrieu, Pete Buttigieg—members of Congress, and others.
Obama had been thinking about 2020 ever since Trump had won, of course, but he’d always kept his cards close to the vest and rarely said anything about specific potential candidates to anyone, especially leery of having his private handicapping become public knowledge. In person in the office, he rarely strayed from the script unless he already knew his visitor, or if someone caught him on an oddly introspective day or asked especially good questions.
In those cases, he liked to talk about his own experience—it took him about a year before he hit his campaign stride in 2007, he said to some, but added that he didn’t fully appreciate how hard the experience would be for himself or for Michelle or their daughters. If the candidates appeared to be onto something, or asked for logistical advice, Obama directed them to Plouffe, but he insisted that if they were really going to do this they’d better be fully convinced of their plan, since there was no such thing as a half-assed campaign.
The thickest-skinned and naivest of the bunch asked Obama to evaluate their strengths and weaknesses. Obama rarely held back, and sometimes this tough talk gave the visitors pause. He was discouraging with Garcetti, for one, figuring the LA mayor wasn’t well known enough and didn’t have a clear enough vision. Garcetti opted against running. More often, they insisted they had what it took no matter what Obama said. After meeting with a procession of wannabes, Obama was unconvinced that many were anywhere close to as prepared for a campaign as he’d been as a novice senator, which was saying something. Some, he thought, had promise but needed to figure out how exactly they would make their appeal. This described Harris. Others still had impressive records but essentially no recognition beyond their jurisdiction, so were bordering on delusional. To Bullock, Obama warned, “The problem is nobody knows you. They know you as much as this guy named Pete.”
This wasn’t a total insult—Obama had actually been impressed by the brains, charisma, and chutzpah of the thirty-something mayor of a small midwestern city. When they’d met, Buttigieg, who is gay, had asked Obama about the nuances of talking about identity on the campaign trail, and spoke confidently about how the party could reach overlooked voters. Obama just doubted it would all add up to viability in a presidential campaign where image and fame mattered immensely—he thought Buttigieg was too short and, as a former volunteer for Obama in 2008, seemed too young—and where such a large field would make breaking through that much harder.
Still, with long-shot candidates he previously knew he was slightly less biting, if still honest. He told Julián Castro, his former housing secretary, that when he had launched his own campaign he figured he had a 30 percent chance of winning. So, he suggested to the candidate with far slimmer odds than that, you never knew what could happen. When he met with Bennet, a quiet but serious senator who wasn’t particularly well known but whom Obama had once considered for secretary of education, the ex-president was encouraging when it came to the actual substance of the presidency. Bennet could be good at it, he said. But, he warned, the Coloradoan had no obvious role to play in a rollicking campaign. How exactly did he propose to stand out? This was going to be a three-ring circus.
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Biden didn’t pay it much mind when he heard Obama was taking these meetings. So were both Clintons and so, for that matter, was he. Obama, however, read 2018’s positive midterm results as vindication of his strategy of stepping back from the daily fray for the party’s benefit, and he started telling visitors more openly that he had no intention of getting actively involved in the presidential primary at all once it started in earnest—especially not to endorse. Biden had always been realistic about this. No one expected him to get his old boss’s formal endorsement from the start, given Obama’s distance from politics these days. But there was also no way around the fact that Obama’s posture was at least a bit of a slight—however implicit—since supporting anyone else would mean rejecting his longtime partner, and he was at least theoretically staying open to it as long as he didn’t explicitly back Biden. It meant he was making the active and ongoing decision not to support Biden. Obama denied this whenever anyone surfaced the notion, of course, invariably insisting that his own tough primary against Clinton had only improved his candidacy, so why shouldn’t he encourage a lively one?
But even beyond the matter of Biden, neutrality was complicated territory for Obama, who had two other close friends considering campaigns, as well. Eric Holder, for one, was talking about 2020, though only preliminarily. The other was former Massachusetts governor Deval Patrick, a close Obama ally who was also friends with Jarrett. Axelrod and Plouffe had worked for him and used his 2006 campaign to test digital organizing methods ahead of Obama’s presidential run. He was Simas’s old boss, too. Obama, though, had a good reason for staying quiet even beyond the awkwardness of his personal relationships. He didn’t want to be seen as putting his thumb on the scale after Sanders’s fans believed the party’s institutions had unfairly handed Clinton the nomination in 2016 and plenty then soured on the Democrats. The party couldn’t afford to see this dynamic repeated.
What Obama did want, however, was to make sure his party picked a winner, and in some of his longer conversations with potential candidates from his technocratic liberal side of the party he mused about how to reckon with the newly empowered left. Even relatively moderate candidates would have to be willing to stretch their usual policy boundaries now, he said, and even if they weren’t comfortable getting all the way to supporting something like Medicare for All, they had to be careful not to diminish the goal of such a proposal. “We’re now in a world where you can’t rule out policies because they’re expensive,” he would point out, a fact he found to be theoretically encouraging but mostly frustrating, considering his insistence on practicality and the political limitations he had faced in 2009 and 2010. Still, Obama was coming around to some new ways of thinking, albeit gingerly. In his first political speech out of office, in September 2018, he’d praised Medicare for All and a handful of Warren’s priorities, like putting workers on corporate boards, as “good new ideas.” Off mic, he was wary about being left behind politically just as his legacy was starting to be debated in the party—he wanted to make clear that he knew he’d been elected a political lifetime ago. The ACA, he would say, was intended to be like a starter home, not a final policy, and the presidency was like a relay race. Progress was the whole point. Still, he’d always end those chats in his office by insisting that a race to the left wasn’t the way to win over real primary voters with real everyday concerns beyond MSNBC’s horse race coverage. He said as much to the victorious House Democrats after the midterms, and tried reminding them that they would, eventually, need to worry about the price tags of their proposals—which at the time included a hotly debated Green New Deal framework proposing historic climate-focused investments—now that they were in power.
His meeting with Sanders was cordial, though their stylistic and ideological differences had only grown since 2016, with Sanders in the Hill trenches and Obama detached from the fray. The senator wanted to make sure Obama wouldn’t weigh in against him, and Obama reassured him and pivoted to his central question: How was the Vermonter planning on persuading people who didn’t already agree with his call for a political revolution? Sanders disagreed with the skepticism embedded in Obama’s question—he thought he would win if he could get as much turnout as possible from usually marginalized groups and disaffected voters—but said he appreciated that it was a rational concern. Obama’s two-hour sit-down with Warren was warmer, which was surely helped by the ex-president’s daughters becoming big fans of the senator and letting him know it. It was a welcome turnaround from his uncomfortable 2017 encounter with Warren. He walked away from the session believing she obviously had more talent than anyone else who might run, and probably more intelligence. He just couldn’t figure out how she was going to win over working-class voters.
As Obama saw it, the challenge for all these candidates was going to be replicating his coalition—blowing out turnout by appealing enough to young voters and minorities without losing too many older whites—which he considered Democrats’ obvious avenue to victory, not a path unique to his talents, profile, and moment. He still hadn’t decided which candidate he thought could get this done by late 2018, and he answered most attempts to figure out the one he favored by insisting he simply wanted to lift up the party’s future leaders, like forty-five-year-old Stacey Abrams in Georgia and thirty-nine-year-old Floridian Andrew Gillum, who’d both narrowly lost midterm gubernatorial races, but neither of whom was running for president. Still, some of his old political staffers were starting to place their bets. Anzalone and Anita Dunn were with Biden, but ad maker Jim Margolis and pollster David Binder signed up with Harris, digital strategist Joe Rospars with Warren, and organizing chief Mitch Stewart, who’d kept close with Obama after he left office, was advising Michael Bloomberg, who was still thinking about running.
In Obama’s innermost circle, however, attention was mostly elsewhere. Obama had watched with interest in the midterms as lanky forty-six-year-old Texas congressman Beto O’Rourke had come shockingly close to winning a Senate seat, raising unheard-of sums of cash and livestreaming his skateboard-and-rock-music-heavy campaign to the masses while building a national following in the process. He was now considering whether to spin that near-success into a presidential run, and some Obama White House alums made no secret that they saw in O’Rourke some traces of Obama’s capacity to inspire, so started emailing around a bumper sticker mockup mashing his “BETO” campaign logo up with the famous O design from Obama’s 2008 bid. Obama dispatched Plouffe to meet with O’Rourke, and the two started talking often, roping in Obama’s former Iowa guru Paul Tewes for sessions in El Paso. Some of Obama’s top donors bought in, too: private-equity exec Mark Gallogly flew to Texas to meet with him and ex-ambassador to the UK Louis Susman started building a network of Obama fundraisers for him on Wall Street. Dan Pfeiffer, the former senior Obama White House advisor, wrote an article making “The Case for Beto O’Rourke,” and as O’Rourke got closer to announcing a campaign he also called Robert Wolf, the former bank exec and Obama economic advisor turned golf buddy.
Some of this was happening in public, or close to it, and was being widely read as implied support from Obama himself. He wouldn’t go that far, but in private he did tell friends that O’Rourke’s Senate campaign had impressed him and he talked to Jen O’Malley Dillon, who was considering taking a job running the campaign, about the importance of stepping up to defeat Trump. She started in El Paso soon after.
Obama’s closest allies weren’t just lining up behind O’Rourke, though. Buttigieg was cultivating a healthy contingent of his own Obamans, largely thanks to his growing relationship with Axelrod, who was talking him up to anyone who would listen. Axelrod saw him as a plausible answer to the question he always asked when evaluating candidates: Who is the remedy to the incumbent? It didn’t take long for Larry Grisolano and Joel Benenson to sign on with Buttigieg, too, or for Obama’s former fundraising chief Rufus Gifford to argue that “Obama was the Pete or Beto candidate in 2007: He was new, he was talking about the future, he was very nontraditional.”
It was Patrick, though—an Obama Foundation board member who kept in regular touch with Obama, Jarrett, and Simas—who got perhaps the most meaningful nod despite being frequently ignored by pundits because he’d been out of office for a while. A few months into Trump’s presidency, Wolf hosted a panel at a hedge fund conference in Las Vegas and gave his two participants, Jarrett and Jeb Bush, a heads-up before they began: he would ask them whom Democrats would nominate next. Bush named Biden, who was also at the conference. Jarrett also knew that Biden was there. She still predicted Patrick.
Her answer raised eyebrows, including Biden’s. He’d started making a show of reading articles about ObamaWorld’s interest in O’Rourke, Buttigieg, and Patrick in particular. “You believe this shit?” he’d ask whoever was around.
* * *
He believed it. Obama and Biden had, for about a year, been trying to make a point of talking every few weeks. The chats were still mostly casual and usually over the phone—they laughed about the publication of a murder mystery novel starring the two of them, which Biden proudly displayed at home—but just as Obama had spent much of 2014 and 2015 trying to divine Biden’s intentions about 2016, he was now trying to work out just how definite his plans were for 2020. Biden sure sounded like he was running, but when their calls turned to politics he used Obama more as a therapist or sounding board than as a political advisor or equal partner. As 2019 approached, Obama could tell Biden was probably going to run, and he told his aides that the ex-VP deserved a serious hearing.
But he had plenty of questions, and even more concerns that couldn’t be easily answered. Obama had whispered to friends that he strongly doubted Biden could create the kind of inspiring connection with the first-to-vote Iowans and New Hampshirites that Obama once had, and which he would need to seriously compete. Obama struggled with what to do with that belief, in part since he hated getting too involved with campaigns that he didn’t think would win—especially in Democratic primaries—and his worry only increased when he asked Biden about who he’d hired for his prospective campaign and heard about only the old, predictable names. It was not, he griped privately, “an A-team” like the one Biden would probably need to get back in touch with the modern party and discourage his worst habits—like his loquaciousness and lack of interest in fundraising—which had helped doom his last campaigns.
