Fortunate One

‘Obama is a preparation freak,’ says one member of his cabinet, who spoke on the condition of anonymity. ‘He makes his own luck.’ Jewel Samad / AFP-Getty Images

As heart-stricken Republicans tried to explain their unambiguous defeat by Barack Obama, some turned to the heavens. Hurricane Sandy, the explanation went, stopped Mitt Romney's momentum in its tracks, gave Obama an exquisitely timed commander-in-chief moment, and blacked out media coverage of his opponent for several crucial days.

The hurricane was merely the latest reason to wonder: have the fates been smiling on Barack Obama? It's hard to look at his stratospheric rise from obscure state senator to leader of the free world in just four years and not think that he might have benefited from a string of extremely good fortune.

True, Obama has faced plenty of obstacles in life. Unlike Mitt Romney, he was not born into great wealth; he is not a member of what Warren Buffett calls the "lucky sperm club." And his race—not to mention a last name that is easily confused with Osama—undoubtedly hurt him with some voters as he ascended through American politics.

At the same time, think about the political luck that has come Obama's way in the last year alone: in a race framed around fears of increasing economic inequality, the president drew an opponent who evoked the Monopoly millionaire. While Obama's admen sought to portray their rival as a hopelessly out-of-touch plutocrat, Romney kept writing their copy. He tried to make a $10,000 bet during a debate, said he was "not concerned about the very poor," and blithely wrote off 47 percent of the electorate as freeloaders. As he moved to the right to secure the Republican nomination, Romney got tangled up in sexual politics, suggesting that companies could deny women contraception. He offended Hispanics with his hardline stance on immigration. And on the night of the most important speech of his career—his address at the Republican convention—the spotlight was stolen from him by a buffoonish Clint Eastwood.

Then, just as Romney was looking stronger—and more moderate—late in the campaign, Obama got an endorsement from Colin Powell, perhaps the country's most iconic centrist. As if that wasn't enough, Hurricane Sandy sparked a politically valuable bromance between the president and Chris Christie, the Republican governor of New Jersey. The storm also led to an endorsement from New York Mayor Michael Bloomberg—who said that, in Sandy's wake, he wanted a president who took the problem of climate change seriously.

"Give me generals who know something about tactics and strategy," said Napoleon Bonaparte, "but best of all give me generals who are lucky." Was Barack Obama in 2012 simply a lucky general? Or was there something more at work than mere good fortune?

Obamacare was in trouble until the high court stepped in. Mark Wilson / Getty Images

While Obama's rise through state and national politics was marked by key moments of serendipity, he time and again exhibited a pattern of meticulous planning—laying the groundwork for, and preparing to take full advantage of, whatever good fortune came his way. "What sets the really good politicians apart from the average ones is the ability to recognize opportunities, prepare for it, and capitalize on it," says Chris Sautter, a longtime political consultant who did early polling for Obama as he was plotting his political ascent.

As a state senator, for instance, Obama made a savvy, forward-thinking move: he managed to get the lines of his district redrawn, pushing its boundaries north into neighborhoods populated by affluent white liberals. By then, he was already eyeing a Senate seat and understood he would need a broader base of support.

In January 2003, Obama jumped into a crowded Democratic-primary race. The leading candidate, multimillionaire Blair Hull, looked like a shoo-in. That was until his divorce papers were unsealed, revealing an allegation that he'd threatened to kill his wife. The revelation was certainly an advantage for Obama—but once it happened, Obama was poised to benefit because of the broad constituency of blacks and wealthy liberals he had begun putting together as a state senator.

In the general election, Obama was pitted against Jack Ryan, a telegenic banker whom many considered the frontrunner. But Ryan's candidacy imploded when his divorce records were aired publicly. They revealed that Ryan had pressured his wife to accompany him to sex clubs. With Ryan out of the race, Republicans were left with eccentric conservative Alan Keyes. Obama sailed to victory.

Even Obama knew he had been lucky in the campaign. "[T]here was no point in denying my almost spooky good fortune," he would later write in The Audacity of Hope. "I was an outlier; a freak; to political insiders, my victory proved nothing."

After bin Laden’s death, Obama’s approval ratings spiked up. Jessica Dimmock / VII Network

Before winning the election, Obama had one more bit of serendipity. Aides to John Kerry, who was then the Democratic standard-bearer, reached out to Obama to offer him an invitation to deliver the keynote address at the Democratic convention in Boston. But here again, it was Obama's assiduous preparation that put him in a position to exploit his good luck. Despite his rich baritone, Obama had not always been a riveting speaker; he was too earnest and wonky. Yet, by the time he ran for the Senate, he'd carefully studied the cadences of black preachers and teamed up with David Axelrod, who counseled him to be a more emotive orator.

For all of Obama's fortune in drawing weak, scandal-prone opponents, he finally drew the short straw when he ran for the Democratic presidential nomination. Going up against the mighty Clinton machine was a true proving ground. And prevailing was another indication that Obama's rise represented something more complicated than a freakish alignment of the stars.

Arguably, Obama got lucky again in the general election, when his opponent John McCain looked erratic by suspending his campaign following the collapse of Lehman Brothers. But what may have been politically fortuitous in the short term was a millstone around his neck once he was elected. The economy was losing 700,000 jobs a month, and if Obama didn't find a way to break the trend, the country was in real danger of falling into a depression.

Yet Obama, who had spent the transition reading biographies of Lincoln and FDR, understood that crises also gave presidents opportunities. So while the sick economy would course through his entire term, obscuring many of his most impressive achievements, he was also laying the foundation for his political salvation.

One of the toughest decisions he had to make early on was whether to bail out Detroit. The country was suffering from sticker shock and simmering over government bailouts. And yet Obama and his advisers understood that letting GM collapse could have led to the loss of as many as a million jobs. What they probably also knew was that the president's reelection might end up hinging on the northern belt of Ohio, which is heavily dependent on the automobile industry.

In the fall of 2009, Obama was at a low moment in his presidency. Populist rage was exploding over Obamacare and bailouts, fueling the rise of the Tea Party; the president's poll numbers were plunging to new lows; and the White House was already fearing losing Congress in 2010. According to Jonathan Alter's The Promise, with another critical health-care vote looming, Rahm Emanuel asked Obama, as the two men sat together in the Oval Office, "Are you feeling lucky, Mr. President?" Without missing a beat the president responded: "My name is Barack Obama, and I'm sitting here. So yeah, I'm feeling pretty lucky." Six months later, health-care reform passed Congress with the slimmest of margins and no Republican support.

The commando operation that led to the death of Osama bin Laden has been characterized by some as Obama's greatest stroke of fortune. After all, had it gone awry, it could have been a catastrophe for Obama's presidency and American morale. But in many ways the raid on Abbottabad, Pakistan, was the classic example of opportunity meeting preparation. First, a strong argument can be made that the chance to get bin Laden only came about because Obama personally reenergized the hunt. Bin Laden's trail had gone cold, and the Bush administration's efforts had grown listless. Almost as soon as he came into office, Obama got the word out that finding bin Laden was a top priority. He began pushing his national-security team to come up with creative, new approaches to the manhunt, and once the intelligence community received its first big break, Obama and his team pursued a data-driven review of their options that would have made Romney proud. The final decision to launch the assault was not a cavalier role of the dice; it was a calculated risk backed up by one of the most elaborate and meticulous intelligence operations in American history.

'Obama is a preparation freak,' says one member of his cabinet, who spoke on the condition of anonymity. 'He makes his own luck.'

The killing of bin Laden was a stunning military and moral victory for the country. But for Obama, governing at a time of such extreme partisan animus and still coping with a torpid economy, a second term was hardly assured. No president since 1936 had won reelection with unemployment above 7.2 percent. Once again, however, Obama was blessed by the weakness of his rivals. And once again he had the skill to exploit it.

Hurricane Sandy gave the president an unexpected boost. Tim Larsen / Lightroom Photos-NJ Governor's Office

The GOP primary field was a freak show that turned into a circular firing squad, which along the way managed to alienate all of the key constituencies Democrats had put together in their 2008 victory: women, Latinos, and even a healthy portion of the white working class, increasingly embittered by rising economic inequality. Obama made the most of the opportunities presented by this Republican rush to the right. To take one example: when Texas Gov. Rick Perry flared up as a brief challenge, Romney responded by taking a hard line on immigration and adding the infelicitous term "self-deportation" to the political lexicon. Hispanic voters were offended, and Obama savvily took the opportunity to solidify their support by unilaterally pushing through a version of the Dream Act—which halted deportation for as many as a million young, otherwise law-abiding illegal immigrants. On Election Day, not surprisingly, Hispanic voters overwhelmingly opted for Obama.

Romney's most important self-inflicted wound came in the form of the infamous "47 percent" video, in which he wrote off nearly half the electorate as moochers. Uncanny good luck for Obama? Partly. But the president had also carefully prepared to take advantage of this kind of divine intervention. Going back to the earliest days of the campaign, Obama and his political team had decided their best plan of attack against Romney was to paint him as an avatar of the 1 percent, the Thurston Howell of the private-equity business. The tape played right into a narrative that the Obama campaign had already laid down—giving it instant resonance. "It reinforced the whole case they had spent months laying the foundation for," says David Corn, the Mother Jones reporter who broke the story.

One of the key traits that allows Obama to capitalize on good fortune is his tendency to take the long view of politics. The Colin Powell endorsement is a case in point. The general's benediction came at the best possible moment, as Obama was trying to build steam heading into the last two weeks of the campaign. In that sense, it may have appeared lucky. But Obama had been consulting with Powell closely throughout his term. The two men met frequently in quiet White House sessions on a wide range of national-security issues, sometimes to the consternation of the Pentagon brass. There are few Washington wise men with whom the president is closer. Powell's endorsement was likely not in question— only its timing.

As Republicans lick their wounds in the wake of their electoral drubbing, they may be tempted to blame their woes on Obama's luck. But that would be self-defeating. They'd be better off finding solace in the fact this is the last time they'll have to run against Barack Obama, a man who is so skilled at both creating and seizing on good fortune. "Obama is a preparation freak," says one member of his cabinet, who spoke on the condition of anonymity. "He makes his own luck."