The long search for Kennedy's successor

This afternoon, when Barack Obama takes the Oath of Office, America's 50-year quest to find a truly transformational leader will finally be over.

(Jae C Hong/AP)

Weeks before the election of 1960, Norman Mailer, already an accomplished novelist, sat down to write his first major work of political journalism, an essay for Esquire in which he argued that only John F Kennedy could save America. In an unruly, haunting and somewhat self-indulgent piece running to nearly 14,000 words, Mailer submitted that a mechanised America, with its bland and automated politics, was on the verge of stamping out individuality and randomness and artistic spirit; the only kind of leader who could rescue it, who could sweep in an era of what Mailer called "existential" politics, was a "hipster" hero – someone who welcomed risk and adventure, someone who sought out new experience, both for himself and for the country. In Kennedy, Mailer saw a man of "not quite describable intensity, a suggestion of dry pent heat perhaps," with "the eyes of a mountaineer" and a penchant for risking his life.

"Indeed, there could be no politics which gave warmth to one's body until the country had recovered its imagination, its pioneer lust for the unexpected and incalculable," Mailer wrote. "It was the changes that might come afterward" – meaning after Kennedy's election – "on which one could put one's hope. With such a man in office the myth of the nation would again be engaged, and the fact that he was Catholic would shiver a first existential vibration of consciousness into the mind of the White Protestant."

As it happened, "Superman Comes to the Supermarket," as Mailer's article was titled, had more of an impact on magazine journalism than on the politics of the era. Mailer essentially created a new genre for a generation of would-be literary philosophers covering politics (most of whom, sadly, lacked for anything approaching Mailer's gift for social commentary). By 1963, Mailer and other idealists were crushed to discover that Kennedy was in fact a fairly conventional, pragmatic politician, more Harvard Yard than Fortress of Solitude. In an introduction to a collection of his essays and letters to Kennedy, titled "The Presidential Papers" and published shortly before Kennedy's death, Mailer vented his bitterness at the general lack of hipsterism in the White House. Kennedy had "the face of a potential hero," he wrote, "but he embodies nothing, he personifies nothing, he is power, rather a quizzical power, without light or principle." In a postscript to his original Esquire essay, Mailer repudiated the article as "propaganda" and said he felt like a traitor for having written it.

No Democrat since Kennedy has rekindled the hipster flame like Barack Obama. (Substitute "African-American" for "Catholic" and there isn't much in that passage about "the myth of the nation" that couldn't have been written by a left-leaning writer today.) The advance sentry for the post-1960s generation, Obama is the first northern Democrat to win the presidency since 1960, the first whose very election seems to mark the opening of a new chapter in the culture. Unlike Jimmy Carter, whose squarish tendencies reassured post-Watergate voters, or Bill Clinton, whose agility as a candidate dazzled and delighted them, Obama seems to his admirers like something apart from politics altogether, as much a social phenomenon as an elected one.

In a sense, the search for Obama – or at least for an Obama-like figure – has been at the centre of American politics ever since Kennedy's death, which came at the tail end of the postwar era, a moment when the glow and shared sacrifice of heroic wars was fading, when the nation's industrial centres were on the verge of a wrenching transformation, when government was about to grow exponentially in size but shrink in prestige. For the next four decades, the dominant narrative in both parties would revolve around outsiders who vowed to remake Washington and its moribund political culture, transcending what Mailer called "the deadening verbiage of its issues, its politics, its jargon". Both Goldwater conservatives and McGovern liberals grew out of this ideal, and a succession of governors turned presidents – Carter, Ronald Reagan, Clinton, George W Bush – made this notion of transformation their central theme. In every case but one (Reagan being the exception), they left Washington more or less unchanged from the way they found it, disappointing both their most ardent followers and all the other reform-minded Americans who had fervently hoped for systemic change.

On a surface level, the modern presidential transition is mostly about bringing order to the minutiae of government and public life – packing boxes, choosing schools, preparing for the policy choices that await and filling some 3,300 federal appointments. In his chronicle of the Kennedy years, A Thousand Days, the historian Arthur Schlesinger Jr described the president's despair at the number of people he had to find to fill 1,200 so-called Schedule C positions. "People, people, people!" Kennedy barked. "I don't know any people. I only know voters. How am I going to fill these 1,200 jobs?"

In a more symbolic way, however, the transition is also very much about this process of forestalling reality, perpetuating the notion of the outsider who has arrived with pick and chisel to breach the ancient crypt of Washington and release its musty air. It is an interregnum of suspended hopefulness, the period after the outsider has asserted his dominance over the system but before he has had the opportunity to become identified with it. His power lies in being perceived, for as long as possible, as a transitional figure, a reformer among insiders; once the transition ends, so, fairly or not, does his lack of accountability for chaotic situations and intractable bureaucracy.

Transitions, in this less literal sense, can end well before a president actually takes the oath of office, or they can last for years afterward. Bill Clinton's transition, for instance, was probably cut short when he lost the fight over Zoë Baird, whose nomination for attorney general was derailed because she hadn't paid taxes for her domestic help, or perhaps when a fight erupted in his first days as president over his pledge to allow gays to serve in the military. Liberal ideologues lost whatever faith they still had in Clinton's purity, independents in his ability to bend government to his reformist will. He had squandered his outsider cachet.

By contrast, Ronald Reagan's transition was lengthened by the nearly fatal attempt on his life less than three months after his swearing in. (The gunman, John Hinckley Jr, shot Reagan and three other men as they exited the Washington Hilton.) How could such an incident not have added credence to Reagan's outsider legend? He had, after all, arrived in the fetid capital as a symbol of popular resistance and renewal, only to have a criminal try to repel him at gunpoint. Reagan's spiking approval ratings in the wake of the assassination attempt afforded him influence over moderates in Washington as well as manoeuvring room with some of his most strident backers, enabling him to negotiate a series of significant legislative victories – including tax cuts and changes to social security – during his first months in office. He remained a president effectively in transition, more a cultural hero (though perhaps not the kind of hero Mailer had in mind) than a practising politician.

Already, in the weeks since the election, Obama has endured the moans of disgruntled constituencies in his own party whose ideal of the outsider is difficult for any breathing politician to fulfil. Progressive activists online and inside the party have complained bitterly about Obama's turning to so many pragmatic insiders – that is, public servants who ran Washington in the Clinton years – to populate his cabinet, rather than reaching out to more academics or state-level politicians whose political instincts have not yet been corroded by Washington's penchant for incrementalism. Then, too, have come the inevitable protests from identity-based interest groups: Latinos and African-Americans in Congress who weren't satisfied with the number of senior appointments, as well as gay activists lamenting the omission of a gay cabinet nominee. That sound you hear is the last wheezing gasp of boomer-age politics, the cataloguing of individuals according to their areas of oppression, the endless process of tallying cultural differences rather than aggregating common objectives. It is a political philosophy that probably made sense 30 years ago but that seems sort of baffling at the dawn of the Obama era, when such interest groups are among the most powerful in the Washington establishment – and when the Man himself is black.

More strenuous tests of Obama's bond with liberal activists are certain to follow. The insurgent nature of his campaign and the sad, spiralling crash of the Republican opposition have now raised expectations for the sort of transformative agenda that no Democrat has dared pursue since the Great Society. Elated Democrats aren't just envisioning a more progressive energy policy; they want an entirely new economic engine built around eco-friendly technologies and a commitment to scrap the internal combustion engine before Obama's daughters get to college. They won't be satisfied with expanding a few existing healthcare programmes; after decades of talk, they want the national overhaul Obama promised, and sooner rather than later. Closing the prison at Guantanamo Bay won't be enough for liberals who want to see investigations and maybe even prosecutions for torture. And yet, in all of these cases, Obama will be tempted – and probably even required – to accept some odious compromises. The bills that emerge from Capitol Hill committees will almost certainly be weighed down with the pet projects of Congressmen grovelling before their constituents and contributors. The legislative process is like Kryptonite to the existential hero; it is designed, somewhat ingeniously, to expose even the most powerful president for the mortal that he is.

If Obama's improbable career to this point tells us anything, however, it is that he is more than simply a brilliant orator and writer with the killer instinct of a born politician; he is also supremely, even confoundingly, lucky. And as the formal phase of his transition draws to a close and this next, less-defined phase begins, he again finds himself wielding some advantages over those who have come before.

First, of course, Obama has inherited a genuine crisis in the impending economic calamity. This might not seem terribly fortuitous, but in fact, nothing extends the outsider's transition or rallies his supporters like a crisis, which is probably why, by mid-December, Obama's approval rating was running north of 80 per cent. The potential collapse of banks and carmakers, while certainly demanding more of his nascent administration than Obama might have hoped, may also allow him to remain aloof from the smallness of governing. Obama doesn't really have to invent an agenda to transform the way Washington operates, nor does he have to concern himself with Mailer's ideal of hipsterism. He simply has to react, ably, to events not of his own making.

In a perverse way, Obama has also been given a Christmas gift that no Democrat of recent decades has enjoyed. Because the nation seems to have reached a Keynesian consensus around the need to spend public dollars to stave off ruin (and because Bush himself has already directed hundreds of billions of dollars in bailout money to the private sector), Obama can propose significant new expenditures without being immediately pilloried as a stereotypical profligate liberal. In other words, he stands to become the first president since the 1970s to unapologetically spend the taxpayers' money – and, more likely than not, he won't have to raise anyone's taxes to do it. No liberal born after Roosevelt could ask for more.

And then there is the technological revolution that has left Obama – the first president to know the narcotic bliss of the BlackBerry – better equipped than any predecessor to maintain his outsider aura and to marshal popular support for his legislative programme. The 20th century was shaped by mass media – first radio, then television – that enabled leaders like Roosevelt, Kennedy and Reagan to help frame the national conversation. What they couldn't do was to enlist their supporters, literally overnight, as a personal army of lobbyists, free from the interference of local party bosses or news editors. This is what the internet gives Obama. Among the myriad ways in which he has benefited from good fortune, one is to have stepped on to the political stage as the theatre itself was undergoing a thorough renovation.

The intensely personal nature of Obama's hi-tech presidential campaign suggests that his supporters may stick to him with more adhesive force than those liberals who found themselves disillusioned with Kennedy or Clinton. It is one thing to vote for a man or even to attend one of his campaign events; it is quite another to have literally invested in him a small chunk of your weekly paycheck – not just once, but repeatedly. (In the end, Obama raised roughly $750m on his way to the presidency, or enough to cover the New York Yankees' payroll for nearly four years.) Those Americans who gave money to the campaign feel more bound to Obama than to any politician in their lifetimes. According to a survey conducted after the election by the Pew Internet and American Life Project, more than half of Obama's online supporters expect to hear directly from the President or his administration in the months ahead, and 62 per cent of Obama voters expect that they will urge other people to support his policies. This suggests an intimacy between president and voter that surpasses anything born of the broadcast age.

This is what technology does, after all – it closes distances. It's not a coincidence that the Democratic convention in Denver last August felt more like a celebration of a personality than of a political party, in the way that conventions normally do. Everywhere you walked in the city, Obama's face – rendered in the now-iconic red, off-white and blue – seemed to follow like the moon, staring down from banners and the sides of buildings, stencilled on to T-shirts, grafted on to the faces of dolls and watches. To a striking degree, voters seem to feel a personal connection with Obama. This is why they refer to him in interviews, routinely, using only his first name. And it's why millions of them are planning to converge on Washington for today's inauguration, despite the probability that they will never even glimpse the man, despite the cold and the chaos and the lack of changing tables or temporary lavatories. They feel as if this is as much their victory, as much their inauguration, as it is his.

This new kind of political relationship comes with not only potential but also peril, and you have to imagine that Obama's technology advisers are trying to figure out how to tap the one without inviting the other. On one hand, they have an opportunity to make this president more immediate and more influential than his predecessors; you can imagine Obama, in the months ahead, video-conferencing with voters or mobilising them by the millions to flood Capitol Hill with virtual petitions. At the same time, Obama's team has to figure out a way to put the presidency online without somehow making the office seem smaller and less regal. This was the lesson – or one of them anyway – from the shrunken presidency of Jimmy Carter, the peanut farmer with the soft voice and the cardigan sweaters who insisted on carrying his own suitcase: Americans like the idea of a people's president, but in practice they prefer him to keep a kind of Olympian remove. We demand that the president know the price of a gallon of milk; we just don't want to imagine him actually standing in the express checkout line.

Even during the transition, Obama's team has struggled with how to make its online ethos relevant to this next phase of his journey, sometimes with painful results. Email messages from David Plouffe, Obama's otherwise-reclusive campaign manager, and others on the campaign have asked supporters to send in $5 for the inauguration in exchange for entry in a raffle (you and a guest could win an all-expense-paid trip to Washington!) or buy holiday scarves with the soon-to-be-President's logo embroidered on them. These kinds of offers are just fine for late-night TV shopping channels, but they strike a discordant tone for the American president at an hour of urgency. Obama's formidable challenge will be to settle on an optimal distance for the digital-age commander in chief, a task requiring him to be more accessible than his predecessors and yet more imperial than he was during his campaign.

After all, it is in no small part his basic elusiveness that makes Obama captivating to so many Americans – not so much the things we know about him as the things we still don't. Obama represents something enigmatic in a political arena where everything before had come to seem trite and depressingly predictable; it's the very newness of him, the lack of familiarity, that makes us wonder if perhaps he signals not only a political departure but also a transformed society. Just maybe, we think, a country that can elect a president as unlikely and untested as Obama is actually less intolerant and less socially stagnant than many Americans had long assumed. "The edge of the mystery" is how Norman Mailer described John Kennedy in 1960, and it may be an apt way to look at Obama too, as he rides up Pennsylvania Avenue obscured by a pane of bulletproof glass. The unfolding years will reveal much more about the man we have elected, and perhaps even something of ourselves.

Matt Bai writes on politics for the 'New York Times' Magazine. He is the author of 'The Argument: Billionaires, Bloggers and the Battle to Remake Democratic Politics', a book chronicling the rise of the first internet-age political movement and the people who built it, which has been compared to both Hunter S Thompson's 'Fear and Loathing: On the Campaign Trail '72' and Joe Klein's 'Primary Colors'. Bai, 39, was a national correspondent for 'Newsweek'. In 2001, he was appointed a fellow at Harvard University's Kennedy School of Government. He lives in Washington, DC.