On the evening of Tuesday, June 30, 2009—just five months into his administration—Barack Obama invited a small group of presidential historians to dine with him in the Family Quarters of the White House. His chief of staff, Rahm Emanuel, personally delivered the invitations with a word of caution: the meeting was to remain private and off the record. As a result, the media missed the chance to report on an important event, for the evening with the historians provided a remarkable sneak preview of why the Obama presidency would shortly go off the rails.

Today, with Mr. Obama in full campaign mode, that event—as well as two more unreported White House dinners with the historians—is worth examining. Together, they shed light on the reason this president is likely to find it much harder than he expects to connect with the public and win reelection to the White House.

At the time of the first dinner, the new president was still enjoying a honeymoon period with the American people; according to Gallup, 63 percent of Americans approved of the job he was doing. Brimming with self-confidence, Mr. Obama had earlier confided to David Axelrod, his chief political strategist: “The weird thing is, I know I can do this job. I like dealing with complicated issues. I’m happy to make decisions.…I think it’s going to be an easier adjustment for me than the campaign. Much easier.”

That the adjustment from campaigner to chief executive would prove harder—much harder—than anticipated had still not dawned on Mr. Obama when he sat down to dine with the historians. He was in an expansive mood as he tucked into his lamb chops and went around the table addressing each historian by name—Doris Kearns Goodwin, Michael Beschloss, Robert Caro, Robert Dallek, Douglas Brinkley, H. W. “Billam” Brands, David Kennedy, Kenneth Mack, and Garry Wills.

During the presidential campaign, most of the evening’s dinner guests, like their liberal counterparts in the media, had dropped any pretense at objectivity. For instance, Michael Beschloss ('Presidential Courage: Brave Leaders and How They Changed America, 1789-1989') described Obama as “probably the smartest guy ever to become president,” which appeared to put Thomas Jefferson in his place.

Judging from Mr. Obama’s questions, one subject was uppermost in his mind: how could he become a “transformational” president and bend the historic trajectory of America’s domestic and foreign policy?

When one of the historians brought up the difficulties that Lyndon Johnson, another wartime president, faced trying to wage a foreign military venture while implementing an ambitious domestic agenda, Mr. Obama grew testy. He implied that he was different, because he could prevail by the force of his personality. He could solve the worst financial crisis since the Great Depression, put millions of people back to work, redistribute wealth, withdraw from Iraq, and reconcile the United States to a less dominant role in the world.

It was, by any measure, a breathtaking display of grandiosity by a man whose entire political curriculum vitae consisted of seven undistinguished years in the Illinois senate and two mostly absent years in the United States Senate. That evening Mr. Obama revealed the characteristics—arrogance, conceit, egotism, vanity, hubris and, above all, rank amateurism—that would mark his presidency and doom it to frustration and failure.

These characteristics had already set the pattern of his administration. Mr. Obama personally conducted his own foreign policy more than any president since Richard Nixon. He made all the decisions, because he believed that only he truly understood the issues. He spent his evenings writing decision papers on foreign affairs when, instead, he should have delegated that chore to experts and devoted his time to schmoozing members of Congress and convincing them to support his programs. He still loved making speeches to large, adoring crowds, but he complained to foreign leaders on the QT that he had to waste precious hours talking with “Congressmen from Palookaville.”


The senior people in his administration proved to be just as inexperienced and inept as Mr. Obama when it came to the business of running the government. Members of his inner circle—David Axelrod, campaign manager David Plouffe, press secretary Robert Gibbs, and éminence grise Valerie Jarrett—had proven their mettle in the dark arts of political campaigning, but they had no serious experience in dealing with public-policy issues. If they could be said to have any policy exposure at all it was their ideological enthusiasms for the left.

Over the two-hour dinner, Mr. Obama and the historians discussed several past presidents. It wasn’t clear from Mr. Obama’s responses which of those presidents he identified with. At one point, he seemed to channel the charismatic John F. Kennedy. At another moment, he extolled the virtues of the “transformative” Ronald Reagan. Then again, it was the saintly Lincoln…or the New Deal’s “Happy Warrior,” Franklin Roosevelt….

Mr. Obama told the historians that he had come up with a slogan for his administration. “I’m thinking of calling it ‘A New Foundation,’ ” he said.

Doris Kearns Goodwin suggested that “A New Foundation” might not be the wisest choice for a motto.

“Why not?” the president asked.

“It sounds,” said Goodwin, “like a woman’s girdle.”

In the wake of the shellacking the Democrats took in the midterm elections in 2010, Mr. Obama held a second dinner with the historians, which was devoted to the question of how he could “reconnect with the public.”

A third dinner took place in July 2011, shortly after Mr. Obama and his team botched the budget-deficit negotiations with Congress, and the United States government lost its Triple-A credit rating for the first time in history. It revolved around the theme “the challenge of reelection.”

That fall, I spoke to one of the historians who attended all three of the dinners. We met in a restaurant where we were unlikely to be seen, and our conversation, which lasted for nearly two hours, was conducted under the condition of anonymity.

I wanted to know how this liberal historian, who had once drunk the Obama Kool-Aid, matched the president’s promise with his performance. By this time, most of Mr. Obama’s supporters were puzzled by the sense of disconnect between the sharply focused presidential candidate of 2008 and the dazed and confused president of the past three years. The satirical TV show "The Onion News Network" had broadcast a faux story that the real Barack Obama had been kidnapped just hours after the election and replaced by an imposter.

“There’s no doubt that Obama has turned out to be a major enigma and disappointment,” the historian told me. “He waged such a brilliant campaign, first against Hillary Clinton in the primaries, and then against John McCain in the general election. For a long time, I found it hard to understand why he couldn’t translate his political savvy into effective governance.

“But I think I know the answer now,” he continued. “Since the beginning of his administration, Obama hasn't been able to capture the public's imagination and inspire people to follow him. Vision isn't enough in a president. Great presidents not only have to enunciate their vision; they must lead by example and inspiration. Franklin Roosevelt spoke to the individual. He and Ronald Reagan had the ability to make each American feel that the president cared deeply and personally about them.

“That quality has been lacking in Obama. People don’t feel that he’s on their side. Obama doesn't connect. He doesn't have the answers. The irony is that he was supposed to be such a brilliant orator. But, in fact, he’s turned out to be a failure as a communicator."

If the verdict of this historian is correct, and Barack Obama’s fundamental failure as president is his inability to connect with people, he is in far more serious trouble than most people realize as he seeks a mandate for a second term in office. Or, as this historian put it: “I wouldn’t bet the ranch on his getting reelected.”

"More than that, Obama might not have the place in history he so eagerly covets. Instead of ranking with FDR and Reagan and other giants, it seems more likely that he will be a case-study in presidential failure like Jimmy Carter."