He was supposed to retire to a triumphant Post-Presidency. Then Trump happened. Now, Obama is gearing up for a political battle he never planned to wage, and has no intention of losing.
The day after Trump’s Election, morning dawned with a drizzle in Washington, D.C. And at 1600 Pennsylvania Avenue, a few dozen White House Staffers crowded into the West Wing office of Josh Earnest, President Obama’s Press Secretary.
But, Barack Obama had summoned them to his office.
The team trudged through the White House corridor, including in their ranks a number of Junior Members who’d never been to the Oval Office before, much less met Obama. They filed in, lined the perimeter wall, and turned their eyes toward the President, who stood in front of the Resolute desk along with Vice President Joe Biden. Obama had been up late the night before, too, watching the Election results. Around three o’clock in the morning, he’d placed phone calls to both Clinton and Trump. But Obama evinced neither fatigue nor despair. Instead, he projected an energized sense of calm.
“This is not the apocalypse,” Obama told the Staffers. He reminded them that despite the Election results, the majority of Americans supported the work they’d done. And he pointed out that the Country had previously weathered periods during which there had been Leaders and Presidents of whom people had been fearful. America had survived, he said, because it’s a strong Country. History, he went on, “zigs and zags.” Obama walked around the office, shaking his Staffers’ hands and thanking them for their efforts. To those who were crying, he offered hugs.
It was a familiar role for Obama. During his time in the White House, he often seemed less Commander in Chief than Consoler in chief. From Tucson to Newtown to Charleston, he had ministered to those living in the aftermath of mass shootings; to those who had lost their homes to hurricanes or wildfires or other natural disasters, he had offered words of solace and a shoulder to cry on. As Valerie Jarrett, Obama’s old friend and Mentor from Chicago, who spent all eight years with him in the White House as his Senior Adviser said, “There’s no one you want with you when you have something traumatic happen more than President Obama.”
And he’s never played that role more than in the aftermath of the Election. In phone calls and in one-on-one meetings, Obama has had to reassure not just his Staff but American and Foreign Leaders, too, that the end is not nigh. “I think he truly believes that,” Dan Pfeiffer, a former White House Senior Adviser said, “People that know him know that he’s an optimist at heart.” But all of Obama’s hopefulness, all of his faith in the strength of America, cannot hide one undeniable fact: For the first time in eight years, as Obama seeks to comfort Americans going through a traumatic event, he knows in the back of his mind that his life has also irrevocably changed. This time, it’s not a town in Oklahoma flattened by a tornado; it’s him.
Before Trump, Obama had big plans for his Post-Presidency. At just 55, he’d be among the youngest former Presidents in American history, joining the likes of Teddy Roosevelt, Ulysses S. Grant, and Bill Clinton, and he was eager to fill his days. He would write a Memoir of his White House years, a book that’s expected to fetch as much as $20 million and that Obama, according to one intimate, hopes will match Grant’s for literary eloquence.
He’d work on his foundation, which would perhaps do even more good than the outfit that the Clintons' run, while likely avoiding anything resembling controversy. “If the Clinton Foundation was about bringing a lot of prominent and wealthy people together and raising money from them to throw at poverty and disease around the world,” says Jon Favreau, the former Obama Speechwriter who’s now advising his old boss’s Foundation, “I think the Obama Foundation will be a lot more about grassroots, bottom-up change, more in line with community organizing.”
More than anything, Obama, and especially his wife Michelle, was ready for a break. And while he didn’t plan to take quite as long of one as Roosevelt, who shortly after leaving the White House went on a yearlong African safari, he planned a lengthy vacation. “He is looking forward to January 21, when he and his wife can hang out and relax and they can just stay up and talk as late as they want,” says Jarrett, “and he doesn’t have to worry about what’s waiting for him in a big briefing book the next morning.” “There was one sort of framework for what his post-presidency would look like, which was contingent on Clinton winning. Then Trump happened and that threw it all in the trash bin.”
Obama, to be sure, will still do all these things, but now they will be done in the shadow of Trump; his angle of repose has suddenly become much sharper. “You can lock in progress for generations if you win three in a row,” says Pfeiffer of the niceties of handing the White House keys to a successor who served in your Administration, as Clinton had in Obama’s. “Some of the battles that would have been settled with a Clinton win will now continue for the next 4 to 20 years.” Another Obama Adviser says: “There was one sort of framework for what his post-presidency would look like, which was contingent on Clinton winning. Then Trump happened and that threw it all in the trash bin. Now it’s Plan B.”
In the weeks since the Election, this Plan B has been taking shape, as Obama has consulted with a range of people, from current and former Advisers to Historians, about how he should conduct himself in his Post-Presidency, doing much of his thinking during long days on the golf course throughout his Hawaiian vacation in December.
While it’s clear that Obama will have to remain more immersed in politics than he’d planned, it remains a mystery what that role will now look like. Certainly he’ll be asked to help rebuild the Democratic Party. Already, Obama has been drawn into the jockeying among candidates vying to lead the Democratic National Committee, a process he expected to sit out. “Nobody wants to know what the Clintons think—they’re totally checked out,” one Obama aide complained in December. “It’s falling on us just by default.”
And in the months ahead, he’ll take a greater role in assisting an initiative, the National Democratic Redistricting Committee helmed by his former Attorney General, Eric Holder, to help the Democrats win back State Legislatures and Governors’ Mansions in preparation for Redistricting after the 2020 Census. He’s mused about being “a talent scout” and “a coach” for the Party’s rising stars.
But the bigger and more immediate conundrum posed by Trump’s Inauguration concerns Trump himself, and the degree to which Obama will break with the tradition of deference and support that outgoing Presidents typically offer their successors.
Obama, who was grateful to George W. Bush for retreating from the public arena and not commenting positively or negatively on his actions, recognizes that with Trump as his successor, he will likely not have the luxury of standing on custom. “Barack Obama today is the most popular politician in America, on either side of the aisle,” explains one Obama White House Staffer. “He has standing. He has vehicles to communicate. And the guy coming in after him doesn’t just threaten his legacy; he threatens the country’s values and institutions. It’d be a violation for Obama not to violate those norms.”
Indeed, Obama may become that rare Political figure with even more sway in the culture than the guy who’s replacing him. “Barack Obama will hold the biggest and most influential megaphone in the world, even when Donald Trump is president, because his popularity at home and abroad will be much greater than Trump’s,” Pfeiffer said. “That’s a resource to be husbanded.”
But how, exactly, does he confront Trump? Obama’s answer to that question, some close to him believe, will be one of the most important decisions of his Political career. Nothing less than his Legacy may ride on it. “The last time he faced this momentous a choice,” Anita Dunn, a former White House Communications Director, recently said, “was when he was deciding whether or not to run for president.”
The day after Obama sought to buck up his shell-shocked Staff in the Oval Office, Trump paid his own visit to the White House. The President-Elect’s entourage was small, just his son-in-law, Jared Kushner; his Press Secretary, Hope Hicks; and a few other Staffers, and his demeanor was uncharacteristically humble. Eight years earlier, Obama had been deeply touched by Bush’s efforts to help him during the Presidential Transition, and he’d vowed to do the same for his successor. Still, Obama hadn’t expected the cocksure real estate tycoon to be as eager for his advice as he had been. After that initial chat with Trump, the very first time the two men had met, Obama told some Aides that he was surprised by Trump’s manner. And when the two continued their dialogue in subsequent weeks, over multiple phone calls, the idea took hold among some in the White House that perhaps the best way for Obama to stay Politically engaged in his Post-Presidency was by exercising as much influence as he could on his successor.
During his time in the White House, of course, Obama was famously averse to buttering up his Political Adversaries. “Why don’t you get a drink with Mitch McConnell?” he once joked in response to complaints that he didn’t spend enough time schmoozing. But some close to him now wonder if he might put aside that aversion to work on Trump. For Obama, cozying up to Trump would require letting go of some old grievances. Trump, after all, repeatedly trashed Obama during his 2016 run; before that, he waged a years-long Racist Campaign that questioned whether Obama had actually been born in the United States. But Obama isn’t one to hold a grudge. “Even in the darkest hour of the 2008 primary, when I’ve never hated anyone more in my life than I did the Clinton campaign staff, he never got to that place,” recalls former Obama Aide Tommy Vietor. “He was better able to disassociate campaign rhetoric from reality.”
And so, some in the Obama White House are crossing their fingers that the outgoing President will keep himself in the ear of his notoriously impressionable successor. At times, that possibility seems hard to imagine, like when, in late December, Trump took to Twitter to complain, “Thought it was going to be a smooth transition—NOT!”. But still they pray that perhaps Obama can exert some influence. “People have this hope, slim as it is, that maybe the president can bring Trump over,” a White House aide says.
“Obama feels he can be effective saying, ‘I was inexperienced when I took the job, here’s what I learned, here’s what it’s like being president,’” one Obama adviser says. “He hopes that by trying to teach Trump how to be president, some of it rubs off.”
They envision the two men continuing to talk after January 20th, over the phone, on the golf course, perhaps even at the White House itself. Obama, after all, will be living in Washington for the next two years, just up Connecticut Avenue, in a rental mansion in the Kalorama neighborhood, while he waits for his younger daughter, Sasha, to finish high school.
As a Member of that tiny fraternity of living Presidents, Obama possesses a unique set of insights that Trump may find invaluable. And unlike more conventional Politicians who assume the Presidency, Trump won’t enter office with a host of settled opinions, or even a coherent ideology. “Obama feels he can be effective saying, ‘I was inexperienced when I took the job, here’s what I learned, here’s what it’s like being president,’ ” one Obama Adviser says. “He hopes that by trying to teach Trump how to be president, some of it rubs off.”
This, however, is a minority view among Obama’s friends and Advisers. They scoff at happy talk of a “bromance” between the 44th and 45th Presidents and suggest that rather than trying to reason with Trump, their best strategy may be to hope that the new President is inattentive. When a Senior White House official was asked to name for the top Obama Policies the Administration hopes Trump will preserve, the aide demurred. “I don’t want to answer that question,” the official explained. “Maybe there are some things that’ll just slip along unnoticed.”
A more likely course of events, say those in Obama’s orbit currently girding for four years of Political war, is just that, an acrimonious battle. Which means the biggest question confronting Obama is just when, and how, to attack.
Does Obama follow the well-worn Post-Presidential path of the occasional New York Times Op-Ed and 60 Minutes sit-down mixed in with some high-dollar speeches to investment bankers and college students? Or does he think outside the box? Although Trump will now control the @POTUS Twitter account, does Obama harness the power of @BarackObama, or better yet, @RealBarackObama to provide a counterweight? A Master Campaigner when he was running himself or stumping for others, Obama could easily continue to give Political Speeches to stadium-size crowds. Either option would represent a virtually unprecedented Post-Presidential role, but then, Obama’s successor is without precedent himself. And as the historian Josh Zeitz notes, “Obama’s the only other person in American politics besides Trump who knows how to use social media and mass political gatherings to advance an agenda.”
Or, in the months ahead, will Obama go even further afield, using his celebrity to challenge Trump’s Agenda in more novel ways? In the days when it seemed likely that Clinton would be taking his place, Obama’s confidants wondered whether he’d buy a chunk of an NBA team or pop up to offer basketball commentary on an ESPN studio show. Now some speculate that Obama might go into the media business. In December, Jake Horowitz, a Co-Founder of the News website Mic, reported that Obama was considering starting his own digital-media company. The White House denied the report, but the media, its opportunities and its challenges, is a serious preoccupation for a soon-to-be Ex-President with a newly urgent message to shape. “It’s very much on his mind,” says Favreau. “He’s a storyteller. Part of what got him into politics was weaving a story together in a way that other Democrats hadn’t done. I think that whatever he does next, figuring out how to weave together a story and a message will be a big part of it.”
While recognizing the extraordinary circumstances of his early Post-Presidency, and the need to dispense with some of the usual customs, some in Obama’s orbit worry that he will squander his unique Political Capital if he’s too aggressive in his criticism of Trump. “Part of what enables former presidents to be so impactful is that they are senior statesmen and not seen through a partisan lens,” Jarrett says. “If you want to be a positive force for good, you can’t get into squabbles on every single issue that involves your successor. You do have to rise above.”
There’s also concern that, even if Obama wanted to go toe-to-toe with Trump, he’d have a structural disadvantage. “People are used to seeing him as president, where he can go to the Rose Garden or the briefing room and have the attention of the world,” says one Obama Adviser. “It’s very different as a former president. It’s a different pulpit.”
The key for Obama will be picking his battles with Trump. “If he was out there all the time narrating Trump’s presidency,” says Pfeiffer, “he’d be squandering his greatest resource. Other Democrats are going to have to emerge to do that. It would not make sense for him or the party to become the voice of the opposition to Trump.” Instead, say those around him, Obama will look for the right moment to re-enter the Political fray, so as to achieve maximum impact. It could be when a key initiative like the Affordable Care Act is repealed or, say, after Trump tramples a particularly noteworthy international norm. “There’s a part of him that looks to not just what could be dismantled but what American values could be brought into question next year,” says one Obama Adviser who has a hard time imagining him staying quiet when he perceives real harm being done. “If a bunch of ‘Dreamers’ are deported,” the Adviser continues, referring to the children of Undocumented Immigrants who were raised in the U.S., “I don’t know that he’ll be able to sit on the sidelines in his heart.” Even before he left office, Obama seemed to be drawing red lines for his successor, devoting much of his farewell address on January 10th to what he called the various “threats” facing our democracy. “Democracy can buckle when we give in to fear,” Obama said, in a not-so-veiled message to Trump. “So just as we, as citizens, must remain vigilant against external aggression, we must guard against a weakening of the values that make us who we are.”
And yet Obama knows that, no matter how popular he is or how great his stature, simply by dint of the 22nd Amendment, his voice can be only so powerful. “People are looking for someone who can make things right somehow,” David Axelrod, who served as the Chief Strategist for Obama’s two Presidential Campaigns, says. “But as high a regard as I have for him, others are going to have to step up who haven’t run the race.”
In other words, as singularly helpful as Obama can be in opposing Trump, he can’t be Liberalism’s lone savior. Tommy Vietor, former Spokesman for President Obama’s National Security Council, invokes the Basketball Coach Rick Pitino, who had a disastrous run with the Celtics in the late 1990s and who once reminded disgruntled Boston fans that pining for a retired superstar is no way to rekindle the glory days. “Larry Bird’s not walking through that door,” Pitino famously told Bostonians. “I feel like we’re going to be channeling Rick Pitino,” Vietor jokes, “and saying, ‘Barack Obama isn’t walking through that door.’ ”
In the weeks after Trump’s win, as new realities grew clearer for the denizens of Obama World, there nonetheless prevailed a grudging sense that this wasn’t how the script was meant to play out. This wasn’t how the Obama years were supposed to end.
A month after the Election, the White House hosted its Annual Holiday Party for the Press in the East Wing, where Journalists and Obama Staffers discussed the incoming President’s latest tweets and Cabinet Appointments. The all-out shock and despair that had pervaded the White House in the initial days after the Election had faded, glum faces and tears replaced by Christmas trees and 15-foot-tall nutcrackers, but no one felt that festive.
The final Holiday Party for any outgoing Administration is always a bittersweet affair, but this one was especially so. The Obama Staffers had originally envisioned it as a rousing send-off for themselves as they prepared to make way for their handpicked successors. Now they acted as if they were getting ready to turn over the building to the bank that had foreclosed on them. One popular topic of conversation that night was whether Trump would even host such a party for the press next year or if he did, whether he’d move it to his new hotel just down Pennsylvania Avenue, so he could at least profit from it.
But underneath the gloom was a surprising amount of resolve. Before Trump’s shocking win, many Obama Staffers figured their Boss’s exit from the White House would also be the occasion of their own retreat from Politics. They’d slide into lucrative Private-Sector gigs, some in D.C., playing the usual influence game; others in Hollywood or Silicon Valley, if they yearned for something a little cooler and less obviously compromising. “We all had visions of our lives where we did our eight years with Obama and that would be the greatest thing we ever do in politics and there’d be no equivalent, so you didn’t want to spend the rest of your life looking for it,” says Pfeiffer.
A more likely course of events, say those in Obama’s orbit, is an acrimonious battle with Trump. Which means the biggest question confronting Obama is when—and how to attack.
In the White House that night, the Staffers who’d soon be out of their jobs talked about their next steps, perhaps hooking on with the 2018 Campaign of a promising Democratic Gubernatorial candidate out there in flyover Country or maybe joining one of the new Anti-Trump Nonprofits or super-PACs that liberal billionaires were getting ready to stand up.
Axelrod, talked about old-time Obama Loyalists who were searching for ways to get back in the mix. “I hope a lot of people who thought they were done won’t be done,” he said. Pfeiffer sounded the same note, predicting that the Obama Staffers were resolute about what lies ahead. “No one will view it as sufficient to sit on the sidelines,” he said. Amid the gingerbread cookies and eggnog, they were once again strapping on their Political Armor. Like their boss, they were steeling themselves for a battle that was somehow just getting started.
NYC Wins When Everyone Can Vote! Michael H. Drucker
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