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Four years ago, I was walking into the Chicago headquarters of the Obama campaign when I ran into one of the then freshman senator's most senior advisers. This man's job was dedicated to what they call the ground game: the relentless work of getting reluctant voters out to the polls across vast swaths of the swing states that decide a presidential election in the US.‘How's it going?' I asked innocently.

‘It would be going a lot better if we weren't trying to elect a black guy called Barack Hussein Obama,' was his deadpan reply.

Four years later, the challenges of re-electing President Obama have moved far beyond cultural and racial questions. Besides the enduring conspiracies about his birthplace and religion, there are three seemingly overwhelming obstacles to Obama's re-election.

Unemployment remains stubbornly high four years after the financial meltdown that led to the loss of millions of American jobs in the last months of the Bush administration and the first months of the Obama term. It is a truth universally acknowledged that no sitting president since the Second World War has won re-election with unemployment this high.

Second, the world represents a volatile series of threats, even though the US has withdrawn from Iraq, and al-Qaeda's leadership has been decimated since 2008. From the violent upheavals after the Arab Spring to the extended crisis of the eurozone, Obama's first term has rarely been a time of peace and quiet.

Third, the rulebook of American campaigns has been torn to shreds, and the new doctrine of presidential elections is one founded more than ever on money. This campaign is a vastly expensive exercise in mutually assured destruction.

There is plenty of blame to go around.

The Republican leadership in Congress met on the night of Obama's inauguration to plot his downfall by denying him a single piece of legislative co-operation with bipartisan votes. That strategy led to Republican triumph in the 2010 mid-term congressional elections but, in a system designed to separate the powers of government, it has produced chronic gridlock and historically low approval rates for Congress. The result has been a hyper-partisan environment that activated the base of both parties but left moderates dismayed. That in turn has helped to shrink the number of truly undecided voters who can be bothered to take part.

The Supreme Court added to this poisonous mix in 2010 by approving unlimited corporate and union spending at election time, on the basis of the constitutional right to free speech.

The result has not been entirely as the court intended, since it upheld the need for disclosure on such spending. Instead, huge anonymous spending - through the outside groups known as ‘super political action committees', or super-PACs, - has come to dominate this election. Political action committees are nothing new in American elections, but the scale and secrecy of these groups now threatens to overshadow the candidates themselves. The old rules - which forced outside groups to avoid co-ordination with the campaigns - have been effectively ignored.

Obama must share responsibility. Four years ago, when he was flush with big and small donors, he became the first presidential candidate since the post-Watergate era to forgo public funds in the general election. At the time he gained a huge advantage over John McCain, who could not match his fundraising and remained within the public system, having to abide by the spending limits this imposed.

But now that strategic decision looks rather less wise. Obama now finds himself the first sitting president to be out-raised by his challenger. The super-PAC aligned with his campaign has been so massively outspent by its Republican rivals that the party was forced to call in the big guns. Rahm Emanuel, the Chicago Mayor and former White House Chief of Staff, is now applying his unique form of verbal pressure on some of the wealthiest Democrats.

All this money - the spending in this presidential contest is expected to be near $1 billion - is chasing a far smaller group of truly gettable voters than existed in 2008.

In the post-convention phase of this election, there were only around 5 per cent of voters who were undecided in recent NBC polls of the most contested states. Those undecided voters look like they may also be unreachable by any amount of advertising. A third of them are undecided about President Obama's job rating. They like Obama personally but hate the direction of the country has taken, and say they are not enthusiastic about the election.

That leaves the Obama and Romney campaigns with a dilemma: do you concentrate solely on turning out your party's base, or do you spend considerable effort and money trying to reach both your core voters and the sliver of undecided voters who might actually show up on election day?

Here is how the two campaigns compare.

Both sides have delighted in trashing the other side. Mitt Romney's business record at Bain Capital has been reduced to the kind of vulture capitalism that even Gordon Gekko would have found distasteful. Barack Obama's healthcare reform has been reduced to the plundering of cash from sickly seniors in need of a hospital bed. Romney would imperil the rights of women. Obama would imperil the security of the United States. Democrats insist their ads are more truthful than those of their rivals. Republicans say their opponents have relied on attacking Romney rather than selling Obama. Both sides are depressingly correct, for the most part.

Most commentators lament that this election cycle is so different in tone from 2008. The more useful comparison is with the election that preceded it. In 2004, President Bush found himself running for re-election at a time when the country had lost confidence in his leadership. Iraq was descending into an appalling civil war, Osama bin Laden was still at large, and the economy was slowing.

But he was blessed with an opponent (like Romney) from Massachusetts who seemed clunky on the campaign trail. John Kerry had a fine record in the Senate, but was then trying to pretend he was more centrist than his liberal record suggested.

Bush set about exploiting those shifts ruthlessly, so that by the time his opponent stood side-by-side on the debate stage - when challengers traditionally look more presidential, and presidents look less so - Kerry was lagging too far in the polls to catch up.

Democrats, meanwhile, fell into the classic trap of blaming everything on a sitting president. While Iraq could certainly be blamed on Bush, al-Qaeda's threat couldn't. Some of Bush's problems were self-inflicted; others were very real.

Obama's campaign has consciously followed a similar track to Bush in 2004. This may be surprising, given their political differences. But many of Obama's aides were on the receiving end of the Bush strategy eight years ago and want to exact their revenge.

They have successfully defined Romney variously as a radical conservative, a chronic flip-flopper, and a corporate raider ill-suited to the task of rebuilding the economy.

All this before Romney managed to respond, in much the same way as Kerry reacted too late to his caricature as a woolly-minded, flip-flopping legislator.

At the same time, Obama's job approval ratings have closely tracked his predecessor's, at the same stage of his presidency. For most of this year, Obama has been less than five points off Bush's approval ratings, and by the post-convention period, he was within two points of Bush's standing at the same point in 2004.

Like the Romney campaign, Kerry's strategists believed that hatred of the sitting president would be enough to drive record turnout. They were correct, up to a point. Kerry won more votes than any candidate before him, Democrat or Republican. Their only problem was that Bush won even more votes than that.

What Bush enjoyed was the enduring loyalty of voters who had invested their emotions and trust in him after the horrors of 9/11. He also profited from the fact that his team built the most formidable turnout machine in American history.

Obama's team in Chicago is using a similar, but significantly enhanced approach. Their candidate still enjoys a surprisingly enduring sense of emotional investment (and yes, hope) from 2008. That's one reason why Obama's personal ratings - his likeability and sense of sympathy - are higher than his job rating.

But that is not enough at a time of 8 per cent unemployment. For most of the past 18 months, Obama's Chicago headquarters has been building the most sophisticated database of voters the world has seen. The Obama campaign has been relentless in its targeting of the voters it considers ‘gettable' in the swing states.

More traditional political strategists see this as a recklessly risky bet. At a time when Obama is being outspent by Romney, the money could have been devoted to more TV advertising. Obama's aides counter that the spread of early voting means the election effectively begins in many states in early October. Turnout operations can no longer wait until the last few days of a campaign.

Romney's aides argue that the pool of undecided voters is unprofitably small. They insist that this election will be decided, much like 2010, by a hugely enthusiastic Republican Party overwhelming a complacent Democratic Party.

According to most polls, this election has remained remarkably stable in recent months. That is despite the huge sums of money spent, and all the storm and fury from Boston and Chicago. This remains a race within the margin of error of the polls, much like Bush's margin of victory in 2004. If 65,000 votes had changed hands in Ohio eight years ago, we could now be approaching the end of President Kerry's second term.

That may sound unlikely. But those are the freakish hypotheticals that drive Obama and his closest aides to continue to fight against the political headwinds. ‘I'm not leaving till I make sure he doesn't turn into a black Jimmy Carter,' said one long-standing Obama adviser. ‘There will be a second term.'

Richard Wolffe is author of Renegade: The Making of a President, and Revival: The Struggle for Survival Inside the Obama White House