Obama watches over himself like a father observing a high-achieving son. Credit: Matt McClain/The Washington Post via Getty Images

August 2, 2021   7 mins

The Obama honeymoon was in full swing. It was March 2009. The inauguration was out of the way, and what a breeze it was going to be, this hope and change business. America was delighted with life. The world was delighted with America (or envious). And Barack Obama, who turns 60 this week, was — understandably — delighted with himself.

Delighted and cool. So cool that he would go on the iconic Tonight Show with host Jay Leno, the first time a sitting president had been on the programme. What a lark. Until the moment when, talking about living in the White House, Obama said he had been practising his bowling in the presidential bowling alley and had scored a 129 out of a possible 300. Not great but an improvement on the embarrassing 37 he had rolled during a stop on the presidential campaign trail a year ago.

“It’s like — it was like Special Olympics or something,” Obama said.

What was he thinking? The Special Olympics provides year-round sporting opportunities for adults and children with learning disabilities. It was started by Democratic party royalty, JFK’s sister Eunice. It is a force for good in the world and a riposte to the ghastliness of the old days when the people who take part could be routinely mocked in public.

And here was Barack Obama, mocking them in public.

He apologised. Boy, did he apologise. And later in his presidency he and Michelle served as honorary chairs of the games.

The incident is largely forgotten now. But it reveals two important facets of the Obama character. His fans point out that he was contrite and decent when he realised his mistake. Critics note, as they did at the time, the preternatural self-confidence — the hubris even — of the man. Why would you even think such a thing — let alone say it out loud — if you didn’t think of yourself as a perfect human specimen and others as less so? And why put yourself in this position so early in your time in office? A White House aide told me shortly after the appearance (I was in Washington, working for the BBC, during the early days of his presidency) that nobody had thought it a good idea to appear on the show, expect the boss.

But then, very few thought it a good idea that he ran in the first place. Even when he was motoring, halfway through the campaign, I met black people in South Carolina who wanted him to pull out. It was too soon. Too dangerous for him and his family. He had a job of persuading to do. Who can blame him if he began by persuading himself?

The family were certainly bemused by the suddenness of dad’s rise to fame and by his single-mindedness in getting there. In his campaign memoir, he writes of an early speechmaking appearance in which one of his daughters grew alarmed at the number of people who seemed to be walking next to their car as they made their way to the venue:

“What are all these people doing in the park?”

“They’re here to see daddy.”


Why, indeed. Obama is an odd mix of immense self-satisfaction and equally impressive ability to see life for what it is. And to see himself for what he is — and, indeed, is not, and never could be. When a crowd of well-wishers holding candles gathers outside his hotel window in Oslo before the Nobel Peace Prize ceremony, he writes that he thought of the wars he was still fighting in Iraq and Afghanistan. “The idea that I, or any one person, could bring order to such chaos seemed laughable,” he says. “On some level, the crowds below were cheering an illusion.”

So, he is supremely self-confident but has a twist of self-awareness. That much we know about Barack. It’s baked into any dispassionate analysis of the man. But what did he achieve? Here, of course, we hit on a problem. Modern America is not given to dispassionate analysis of anything, let alone Obama.

It is fair to say that a good number of thinkers on the Left (thinkers, rather than political doers, who know the limits or accept them more) are looking back on the Obama years as a missed opportunity. A famous American football coach once said, “show me a good loser and I’ll show you a loser,” and there is a frustration at the years wasted to a fruitless effort to do business with an already-radicalised Republican party. Compromise was sought endlessly when it was never really available. Obama, the thinking goes, should have pushed on with NHS-style, free-at-the-point-of-delivery healthcare; he should have fought harder for the rights of the oppressed, and done fewer deals with the bosses. He could have been less pally, after office, with George W. Bush, less keen on Netflix deals and Martha’s Vineyard sojourns; grittier, angrier, moodier.

To which there is an obvious reply: let Obama be Obama. He was never going to do these things. He was a member of the Democratic party but because of his signal achievement in getting elected, he was a semi-detached member by the time he got to the White House. He had outgrown it. And he treated the nuts and bolts of keeping it alive with some disdain.

In part this was a personal failing. He is too calm, too apt to shrug and smile. There’s not much badness in Barack. No devilment, no desire to gamble. His favourite music is complex more than majestic: the Bach Cello Suites. It’s my favourite too, but nobody’s ever accused me of wanting to change the world.

Obama came to power suggesting he did. He wanted his presidency to be “transformational” — to re-imagine America in the way Reagan did — but he was hampered as much by his own personality as by the politics of the time. In his memoirs he gives the impression of watching over himself like a deity keeping a proud eye on a high-achieving son. It’s all very controlled. He had the pride of Shelley’s Ozymandias but he would have foreseen as well the decay, the lone and level sands.

His own take on his political philosophy is the most revealing sentence of his presidential memoirs: rather than having a “revolutionary soul,” he says, “I was a reformer, conservative in temperament if not vision.” He adds: “If every argument had two sides, I usually came up with four.”

Ok, he was too thoughtful. We get it. The party gets it. That was his personality. But when it came to politics, was he also not thoughtful enough? Did he not realise something that he should have realised — something that led not just to missed opportunities for community building but to something far more sinister, far more fundamentally sapping?

It seems to me that the more damaging charge is that he laid the groundwork for the Trump years — the anger and hurt and widespread dislike of the Democrats that lead to Trump — because he genuinely thought that making his mark and strutting his stuff would be enough. He once promised that the sea levels would stop rising under his presidency; the globe would heal. He had large ambitions, but did he have the political energy to make good things happen?

The answer may well be no. Remember he had built what was, in 2008, the most extraordinary campaigning network in human history. They had 13 million email addresses, 3 million individual donors, tens of thousands of whom had set up networks to raise money from their friends and colleagues. They knew a good deal about these people, too. Although Facebook was a thing, it was not yet the biggest thing: the explosion of social media had not happened. The Obama movement was ahead of the curve.

And it all went to waste. Team Obama saw it happening. They tried to interest the new president but he was unpersuadable. In an article in the New Republic written just after Trump had taken office the author and backer of progressive causes Micah Sifry did not hold back:

“It was the seminal mistake of his presidency — one that set the tone for the next eight years of dashed hopes, and helped pave the way for Donald Trump to harness the pent-up demand for change Obama had unleashed.”

Nobody really knows how many Obama voters turned to Trump in 2016 — people are unreliable witnesses to their previous habits in voting as in much else — but the number could be at or above 8 million. That is a good deal of hope down the drain. An election-losing amount. A party with its campaigning ear to the ground would have picked up the extent of the anger festering in rural Pennsylvania, in the rust belt, in Florida. Instead the party chose Hillary Clinton and persuaded itself that all was fine.

In Obama’s defence, it’s worth noting that he came to office in the midst of the financial crisis. He had a lot on his plate. But his ability to cope had been his calling card. “I’ve got this,” he would tell nervous aides. And he always had until then. The failure to re-energise the party as a listening and intelligence gathering machine was in part bureaucratic. But Micah Sifry still points the finger of blame at the boss.

There has always been a tension in Obama between energetic involvement and languid detachment. It is downright weird that this man arguably prevented a huge economic depression in 2009 and gave health insurance for the first time to all Americans — but in the process lost touch with them and started to annoy them. Typically, he appreciates the weirdness himself: in his memoir he writes that Franklin D. Roosevelt “would never have made such mistakes.”

“I found myself wondering whether we’d somehow turned a virtue into a vice; whether, trapped in my own high-mindedness, I’d failed to tell the American people a story they could believe in.”

When Obama first debated against the Republican candidate Mitt Romney in 2012, there was more than a hint of the political aimlessness that had infested the whole enterprise. James Carville, the Clinton-era Democratic campaigner, told CNN he had been left with “one overwhelming impression … It looked like Romney wanted to be there and President Obama didn’t want to be there. It gave you the impression that this whole thing was a lot of trouble.”

He pulled that campaign around but never again achieved the heights he had when he came to office. Now he lives in glitzy obscurity, you might say irrelevance. He brought a huge amount of hope and not much change. He allowed a semi-true narrative to take hold: that he had backed the bankers not the people after the financial crisis. It allowed the Tea Party movement to take hold, driven also by racial animus and longer-term dysfunction, and the rest, as they say, is history. Trump, the modern-day Republican party and a serious question that can honestly be asked now: will the 2024 presidential election be disputed in a manner that calls into question the future of American democracy?

That was not the plan. And it is certainly not the fault of one man. But if you pose as a big figure you have to live with the consequences. When I interviewed Obama in 2009 he offered to write a message for my children on a sheet of paper: “Dream big dreams, Martha Sam and Clara.”

To which history might add: “…though it won’t be enough.”

Justin Webb interviewing Barack Obama in 2009.

Justin Webb presents the Americast podcast and Today on Radio Four. His Panorama documentary “Trump the Sequel”, is available now on  Iplayer