With 100 days left in the presidential campaign, perhaps the two most vexing questions in American politics are: How could President Obama possibly lose? And, how could he possibly win?

Americans are scared, angry and struggling. They used to talk about job satisfaction; now they talk about just holding on to their jobs. No incumbent since FDR has ever won reelection with unemployment numbers remotely resembling today’s. What voters feel about their lives and dreams in the months leading up to an election tends to stick to the president when they enter the voting booth. And right now what’s sticking to Obama isn’t good.

But it sure helps to face a candidate as uncomfortable in his own skin, as likely to say by accident what he really means and as wrong for the times as Mitt Romney. In an era when even conservatives are populists, enraged about the favors granted the rich and well-connected, Romney is running as a CEO who thinks his taxes are too high. Voters just aren’t warming up to a guy who enjoys firing people and attempts to woo the people of Michigan by referring to his wife’s “couple of Cadillacs.” If Obama offers what well-paid elites call a “jobless recovery,” Romney offers the only thing worse: a promise to restore the policies that led to the joblessness that made a recovery necessary.

So, beyond the anemic economy, why do the latest polls show the former Massachusetts governor in a dead heat with the president? Because Obama’s administration made three crucial errors that enabled the Republican obstructionism that has tied his hands for the past two years, with GOP leaders shooting down any idea — even if it’s one of their own — that might have helped the president strengthen the economy. And those mistakes have made possible what was unimaginable in January 2009: that a private-equity baron lacking a sense of noblesse oblige, and preaching the gospel of deregulation and lower taxes for the rich, might actually win the presidency four years after those policies led to the collapse of the U.S. economy.

Obama’s first mistake was inviting the Republicans to the table. The GOP had just decimated the economy and had been repudiated by voters to such an extent that few Americans wanted to admit that they were registered Republicans. Yet Obama, with his penchant for unilateral bipartisanship, refused to speak ill of what they had done. The American people wanted the perpetrators of the Great Recession held accountable, and they wanted the president and Congress to enact legislation to prevent Wall Street bankers from ever destroying the lives of so many again. Instead they saw renewed bonuses — and then they saw red. Republicans learned very quickly that they could attack Obama and his agenda with impunity. Only at election time, or when he’s up against the ropes, does this president ever tell a story with a villain.

The second mistake was squandering the goodwill that Americans felt toward the new president and their anxiety about an economy hemorrhaging three-quarters of a million jobs a month. That combination gave Obama, at the beginning of his term, a power to shape public policy that no one since Franklin Roosevelt had held. But instead of designing a stimulus that reflected the thinking of the country’s best economic minds, he cut their recommended numbers by a third and turned another third into inert tax cuts designed to appease Republican legislators whose primary aim was to defeat him. He stimulated the economy — but just enough to leave the results open to interpretation, rendering questionable what should have been an uncontested success.

Obama compounded the problem a year into his presidency, when corporate profits were on the rise while job creation wasn’t. The Senate was considering a jobs program much like one the House had passed. But Obama refused to throw his support behind it. To do so, he would have had to articulate a vision in which government sets the conditions for the private sector to create prosperity and jobs, and steps in when the private sector can’t — or when it works against the interests of ordinary Americans. It’s a vision in which leadership means knowing when to step up and when to step back, not simply passively riding the waves of market failures, business cycles and bubbles — the vision that unites Herbert Hoover, George W. Bush and Romney.

But Obama chose neither to offer that vision nor to take action to put Americans back to work directly, rebuilding our broken roads, our bridges, our crumbling schools. The stimulus was a good start, but its flaws were already apparent. Instead, he began using Republican language about how the government, like ordinary families, needs to tighten its belt, as if that were a solution for people whose belts couldn’t get any tighter. “Government has to start living within its means, just like families do,” he said in a weekly Web and radio address. Words like these not only undercut the vision behind the stimulus — the whole point of which was to spark a sputtering economy with deficit spending — but they came as bankers were loosening their belts, making average Americans angrier.

The third way the administration created opportunities for Republican obstructionism will someday become a business-school case study: It let a popular idea — a family doctor for every family — be recast as a losing ideological battle between intrusive government and freedom. In the 2008 election, the American people were convinced that families should never have to choose between putting food on the table and taking the kids to the doctor. They were adamant that neither they nor their aging parents should have to choose between their medicine and their mortgage.

How did the administration manage to turn one of the most popular campaign issues of 2008 into one of the major causes of Democrats’ “shellacking” at the polls two years later?

In keeping with the most baffling habit of one of our most rhetorically gifted presidents, Obama and his team just didn’t bother explaining what they were doing and why. To them, their actions were self-evident. But nothing is self-evident when your opponents are spending millions of dollars to defeat you. Instead, the White House blundered around with memorable phrases such as “bending the cost curve,” which didn’t speak to the values underlying the need for health-care reform.

Republicans, in contrast, offered a coherent story: Democrats think the government knows what you need better than you do; you should be able to make your own choices, not have some bureaucrat stand between you and your doctor. The White House could have counterpunched, but instead it dropped its gloves.

The president acknowledged as much this month in an interview with Charlie Rose for CBS. When asked about the biggest mistake of his first term, he replied it was his belief that “this job was just about getting the policy right. And that’s important. But the nature of this office is also to tell a story to the American people that gives them a sense of unity and purpose and optimism, especially during tough times.”

To his credit, Obama has been telling a much better story over the past several months about the challenges ahead and why he deserves a second term. “We can either settle for a country where a shrinking number of people do really well, while a growing number of Americans barely get by,” he declares in his new campaign message, “or we can restore an economy where everyone gets a fair shot, everyone does their fair share, and everyone plays by the same set of rules.”

But the problems of health-care reform were not just about selling it — they were substantive as well.

There was no way to tell the story of why the government couldn’t negotiate prices for drugs with the big drug companies, the way the Department of Veterans Affairs already does, without admitting either that the administration was buying off the pharmaceutical industry or that the industry was buying off the administration. There was no way to explain why Americans who saw how much their parents or grandparents liked Medicare couldn’t have at least one option not controlled by the insurance industry — without admitting that the administration had made a deal with the industry that guaranteed it 30 million new customers with no government competition. As Ron Suskind reported in his book “Confidence Men,” that decision ended any possibility of a “public option” a year before the president announced, without explanation, that the public option had died on the operating table.

Whereas the House, under the leadership of Speaker Nancy Pelosi (D-Calif.), put forward a sensible health-care bill in the early days of the new administration, the White House and congressional Democrats ultimately crafted a bill whose greatest benefits would become apparent only years later, giving Republicans all the time in the world to galvanize public opinion against it. Democrats frequently point out that most of the elements of the law are extremely popular, even though the law as a whole remains unpopular. They’re absolutely right. But that’s like saying people pick a spouse based on the person’s nose, mouth, shoulders, hair, job, personality and earning potential, when in fact it’s the totality of the person that either does or doesn’t make our hearts flutter.

One of the most popular elements of the health-care law, and the one that matters most to middle-class Americans, is the end to insurance companies’ ban on people with “preexisting conditions.” That part of the law came online in 2010 for children, an enormous achievement. But our bodies generally start falling apart in our 40s and 50s (trust me on that), and nothing could have been more important for the success of the legislation — and the party and president who made it the law of the land — than for Obama to have been able to pronounce as he signed the bill, “With this stroke of my pen, never again will any American ever see the words from an insurance company, ‘Rejected: preexisting condition.’ ” Try repealing that.

By delaying that part of the law until 2014, along with provisions designed to cover 30 million more people (unless Republican governors refuse federal funding to extend Medicaid), the Democrats lost the message war. Nothing blunts the fierce urgency of now like the soft promise of later.

Obama has every reason to feel underappreciated. Both the stimulus and health-care reform were kinda-sorta the right policies. The stimulus was not, as conservatives have convinced many of their fellow Americans, big government on steroids; it was Keynesian economics on birth control. It did not restore the 8 million jobs lost to the crash of 2008 or provide the 200,000 jobs a month needed for new entrants into the labor market, but it did prevent a second Great Depression. The health-care law was no more a prelude to a long march to European-style socialism than the similar bill Richard Nixon proposed 40 years ago — or the law Romney enacted as his greatest legacy to the people of Massachusetts.

So how did the White House make mistakes of this magnitude, which have breathed new life into Republicanism and made a Romney administration a possibility?

One factor is the tyranny of money in our nation’s politics. That two administrations — one Republican, one Democratic — bailed out the banks instead of the people on whom they were foreclosing is an outrage that reflects the legalized bribery we call campaign financing. The bottom line for corporate executives is “return on investment,” and the return on Wall Street’s bundling and lobbying has more than made up for the failures of its bundling of toxic assets.

But just as important is the tyranny of timidity. If self-interest and self-righteousness are at the heart of the Republican Party today, cowardice lies too close to the spine of the Democrats. While Republicans show extraordinary hubris by harnessing minority rule on virtually every issue with just the threat of a filibuster, Senate Democrats show extraordinary fearfulness in enabling them. In the past, Democrats spoke openly of poverty, a word seldom heard today even though Americans of every race and color are sharing a rapid descent down the economic ladder. While the president has begun to speak effectively in the past several months about the economic distress of working- and middle-class families, on the major issues he too often uses the bully pulpit to bully the truth.

That was most apparent in the first three years of his administration, but you don’t have to look further than the past three weeks. The nation has experienced climate change firsthand, with Americans witnessing extreme weather, drought, wildfires, floods and harvests destroyed by the scorched-earth policies of the oil and coal industries. But Obama, like his challenger, has simply turned up his air conditioner, refusing to connect the dots between the devastation people can see and the causes they are finally ready to accept.

And a week ago, the nation was in shock after yet another mass shooting, allegedly carried out by yet another troubled young man who had purchased weapons that should not be legal. The first day, Obama and Romney issued the usual comforting platitudes about how our prayers are with the victims’ families. But in its public statements, the White House seemed more concerned with reassuring the National Rifle Association than with giving voice to the desire of a bullet-ridden nation to protect the rights of law-abiding citizens — those who want guns to hunt or protect their families and homes, as well as those who want to go to the movies, church, school or a shopping mall without fear. To his credit, Obama gave a speech Wednesday before the Urban League calling for “common sense” steps to prevent gun violence, although it was long on hope and short on change.

Obama may be reelected by a public that has nowhere else to turn. Perhaps freed of the constraints imposed by having to raise a billion dollars to finance his campaign, he will reveal a true self of which we’ve seen glimmers. One who will speak forthrightly to the American public and be unafraid to take on the perpetrators of economic crimes that have devastated American families; the perpetrators of myths about “clean coal,” which the president instead repeats even as the industry rains fire on America’s breadbasket; or the perpetrators of the record foreclosures on longtime homeowners who have become collateral damage in the war on the middle class.

We can only hope that in his heart, Obama can truly feel the pain, sadness and fear of ordinary Americans, because it’s not hard to imagine that inside the chest of his opponent is a cavity waiting to be filled.

Drew Westen is a professor of psychology and psychiatry at Emory University and the author of “The Political Brain: The Role of Emotion in Deciding the Fate of the Nation.” He is the founder of Westen Strategies, a consulting firm.

Read more from Outlook:

Let’s just say it: The Republicans are the problem

Romney’s tax returns, Obama’s birth certificate and the death of trust

Five myths about Barack Obama

Still waiting for our first black president

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