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

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?”
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.”

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SubscribeWell done Mr Gutman for having the courage of your convictions.
“In the dystopian novel Nineteen Eighty-Four (1949), by George Orwell, the Two MinutesHate is the daily, public period”
Today I await the Two MinutesSelfHate becoming a daily school ritual. (those who are not White may do the Two Minutes Hate)
It may happen soon: https://www.city-journal.org/critical-race-theory-portland-public-schools
I grew up with three sisters. I think if I had been forced to attend a session like that and been treated that way I would still be in jail for slapping that b**** into the following week.
The teachers should quit rather than face this abuse.
The link you provide is truly terrifying; West civilisation is rapidly building its own funeral pyre.
It is so heartening to hear from a parent who genuinely loves their child and won’t let them be subject to propaganda.
Massive respect. Wonder if this got any mass press coverage over there as it should have. One of, if not the only, example of good people putting their foot down and having the integrity and decency to reject these quasi-religious fanatics and their grotesque, obscene, bullying BS. I dearly hope it’s the start of real substantial resistance. It makes me want to start a group to march against political indoctrination in the UK, which is the biggest threat to a stable, sane generation of people, and future ones after them that exists right now.
It’s not the old, fluffy liberalism we are facing. And we can all feel the hatred, malevolence, and toxic resentment of these despicable, damaged, anti-social nightmare group.
Political indoctrination and 1984 social engineering, domestic abuse, child abuse, those are critical things people should be striving for to change. Instead, we’ve got Antifa headcases in far too many positions of influence, and they’re utterly unable to keep themselves from abusing the minds of kids as soon as they get the chance. They only care about people using the right pronouns they demand be used for them and idiocy like that.
I left the UK for various reasons in the early 2000s. One reason was the children`s education.
I could see already the way it was going as I lived in London in a bourgeois area but with even then quite a lot of diversity. I do not really have the money without a struggle for the private sector, and anyway I prefer the state sector if it is run well.
I thought it would be a bad thing if frequently the children were to come home, tell me what they had been told about the world, and I would have to tell them that is not a fact, it is an opinion, and I believe it is wrong for the following reasons. It undermines their belief in authority at too early an age, and in fact it would be reasonable for a child to think the teachers were perhaps talking nonsense even about more factual matters like maths or physics.
I think I made a good choice – the country my wife was born in, where politics and ideology make little (although even here, a little) intrusion into the schools. I think they have had a good education – although no doubt many UK educators would be appalled at their lack of, or even opposition to, wokeness.
“I thought it would be a bad thing if frequently the children were to come home, tell me what they had been told about the world, and I would have to tell them that is not a fact, it is an opinion, and I believe it is wrong for the following reasons. It undermines their belief in authority at too early an age”
I never had a problem telling my son from a young age that his (London, state school) teachers could be wrong about stuff. Maybe that’s a bit aspergery, but he seems to have worked out ok – and he’s very adept at telling people what they want to hear.
It is a question of degree. To say that a teacher got a fact wrong or made a spelling mistake – fine.
To say that a large number of the teachers in a school are constantly repeating wrong things on important matters, and their views on life in general are valueless, nay harmful – that is different.
One memory my wife has was a primary school teacher telling her how lucky we were that the children in the school spoke lots of different languages – and of course, virtually daring my wife to disagree that there could be downsides to such a Tower of Babel. And that is just a minor example.
Where is this promised land, please?
Sorry, Jonathan, people I know might guess who I am. I will merely say it is not in northern or western Europe – but then you probably knew that!
But you know, maybe it could be lots of countries outside northern and western Europe and the Islamic and sub-Saharan African world.
Wokeism is a secular counter-Enlightenment movement. It’s the first time a secular critique of Enlightenment went mainstream and I think this took many by surprise.
There’s also the political angle. It helps Democrats cast the widest net for minority vote at a time of right-wing populism in US. It looked like it was working in pushing the Right back for a while.
But now, a valid question is whether this will all backfire and strengthen right-wing populism after all, by potentially providing confirmation for some of the things far-righters had been saying about the establishment (e.g. political correctness gone mad) for large parts of the population (e.g. trans rights movement, defund police, white fragility, …).
In Australia they are teaching very young children that Jesus was non-binary and wore a dress. We learned this from a video of a bewildered Aussie mum on Alex Belfield’s Voice of Reason podcast this morning. Notwithstanding the fact the religion should not even be taught in schools, this is crazy even by the standards of what passed for education in the West today.
“Notwithstanding the fact the religion should not even be taught in schools,”
Religion SHOULD be taught in schools! To say otherwise is like saying history should not be taught in schools as people disagree on its meaning. Or literature should not be taught as there are too many viewpoints so some must be wrong, and those could hurt innocents…..
As religion has been mans greatest accomplishment in arising from the savanna – grubbing roots and clubbing zebras – into forming structured societies with philosophical concepts, agreed morality, and set organizations of educated leadership.
I did not know you were one with the modern cancel culture, or a knee-jerk atheist.
Am I a reactionary atheist if I object to creationism being taught in schools?
Awaiting approval above for word j ** k, so repeated below with offending letters redacted:
“Notwithstanding the fact the religion should not even be taught in schools,”
Religion SHOULD be taught in schools! To say otherwise is like saying history should not be taught in schools as people disagree on its meaning. Or literature should not be taught as there are too many viewpoints so some must be wrong, and those could hurt innocents…..
As religion has been mans greatest accomplishment in arising from the savanna – grubbing roots and clubbing zebras – into forming structured societies with philosophical concepts, agreed morality, and set organizations of educated leadership.
I did not know you were one with the modern cancel culture, or a knee-*e r* atheist.
“teaching very young children that Jesus was non-binary and wore a dress”
My guess is they will not go into explaining Mohammad wearing a dress as well, but keep him in his dishdasha. Purely to be culturally sensitive, and to avoid any inconvenient beheading.
What the major religions purportedly believe should be taught in schools (would be nice to catch some of the minor ones too) alongside a historical analysis of whether followers of those religions have practised what they preached.
I have a family member in the state school system in a Republican state. Every subject, somehow or another, has to include Wokeness, from computing (you must acknowledge how others feel) to geography (oppression is everywhere), by my estimate 20% of teaching now is Woke, in every subject. I shudder to think what they teach in Oregon, California, etc.
I wish Mr.Gutmann well, and I do, truly, hope it works out. I suspect that it will be massively over-subscribed.
How about looking at what is happening in schools in England?
https://www.dailymail.co.uk/news/article-9557845/School-reports-chaplain-telling-pupils-theyre-allowed-disagree-LGBT-teaching.html?ito=email_share_article-top
Gutmann seems like he would have been fine with actual anti racist policies. But that isn’t what Brearley was implementing. Its policies were distinctly racist. Just calling them anti-racist when they were, in fact, the very opposite, is designed to squelch dissent against racist policies. Bravo to Mr Gutmann for standing up to them.
I also think mr Gutman would merely trim the extreme, but set up a school which would still be way Liberal/Left for a typical, Non-NYC-rich guy. That ‘Thanksgiving will always have a foot note to dead Native Americans, and Imperial India history be about British exploiting the natives., with some bits of architecture, and their religion, and civil rights (and maybe even the millions killed during the partition, but maybe not, depending who is made to be the bad guys.) so much better than normal schools, but Liberal.
Not that it will matter as he clearly explains the entire function of the $54,000 a year school is to feed into $70,000 a year universities and so into $1,000,000 + per year jobs amongst the right sorts of people.
In the Daily Mail today is a NYC liberal school teaching kindergarten children about master***ion using sexual correct cartoon characters. I would have the person presenting this class charged with pedophilia to be a lesson to all adults to not get weirdly into this kind of situation with children.
Yes, one of my daughters attended a university which was about $48k tuition and room and board. The first year all parents got a letter apologizing because some fraternity on campus had a cowboys and Indians party with some questionable dress on the part of the “Indian” attendees. And they were serious. I guess the administrators never attended college themselves. She found it amusing that anyone would apologize for this and any “offense” it caused and so did I. As Jerry Seinfeld famously said…..”if I like their race, how can it be racist?”
They are college kids, showing up at parties inappropriately dressed is what they do. I’m fine with liberal beliefs and my kids were all armed with an explanation of what they might see and how not to over-react. How not to walk around with a huge chip on their shoulders.
A good and brave man. One can only hope that he manages to establish his new type of school in New York, and that this leads to more such schools across the US.
I think the idea of a parallel school system for people who want to avoid the rapid shift in the woke direction is a terrific idea. I’m happy to hear he actually has some momentum and money behind the idea. I applaud his initiative. I’m very worried, however, that what we’ll end up with is 20% of kids getting a decent education while 80% are in public schools getting the indoctrination. I’m just guessing at the percentages. But, even if it was 50/50, it seems like there is a dark future ahead for these kids and our country. I don’t see ‘a more perfect union’ in the future if CRT and all its baggage is allowed to be taught. It is inherently divisive. Its goals include basically tearing down the government and educational structure of the nation and starting over. I applaud parents getting their kids away from this ideology, but there are still going to be millions of kids being indoctrinated. This isn’t going to end well.
A courageous and principled man. Just a question…. I thought that Biden had signed off CRT for all schools at the beginning of the year?
Biden doesn’t have the power to do this. In addition, some states have banned CRT in public schools. Presidents aren’t monarchs.
Raised Catholic but never believing in original sin, I see here a repetition of that obnoxious doctrine: born white, you are born more or less a psychopath, or vicious oppressor, etc. I later learned that the Eastern CHurch has a different and older definition of what is called the sin of Adam and Eve: we all bear the consequences of that sin (the cruelty and inhumanity we so easily inflict on each other and, yes, class and racial oppression) but we bear no guilt. We are only guilty of the sins we ourselves personally commit.
We are only guilty of the wriongs we ourselves commit. And those wrongs can be repaired by a non-ego focused acknowledgement of them, a resolution to do those wrongs no more, and action to perform what reparation we can.
Racism certainly exists and is deeply ingrained in our society. So is the easy assumption of superiority by the class of one’s birth, or by “meritocracy.” The wrongs of society need to be explored with a view to advancing justice. A medieval theological approach does not advance justice or challenge the priviliged to stop fcusing on themselves and their guilt and instead focus on social and class realities with a commitment to advance solutions to the wrongs that are there. I favor ecomnomic security for everyonne and access to certtain resources for everyone. in other words, a well regulated social democratic form of a capitalist economy and democratic governance. But other approaches can be discussed, especially ones that assure economic security and the right to govern one’s own life without hectoring form preachers (religious or secular, right or left) within an orbit of relationship and civic obligations.
Dwelling on one’s guilt is a form of egoistic focus on one’s self. Focusing on shared problems and solutions is one way we escape the human dilemma and harm of egoism.
I am sure there are good aspects of critical race theory. But a far better way to confront and work out solutions to our race (and class) problems are avaiiable. Parents need to discover what has been emppiricalluy proven to solve poverty, class, race and police problems and demand that these solution oriented approaches be taught. A good resource, one that catalogs proven effective solutions, is the Shriver Center at the University of Maryland.
We all remember Martin Luther King’s, “I look to a day when people will not be judged by the color of their skin, but by the content of their character.” This humanistic approach, respectful of people of good will from all backgrounds, did not prevent him from seeing the injustices perpetrated on working class people, especially blacks and other not mainstream white populations, and aiming for radical economic reform as a result.
It certainly seems as though the advance guard of the Woke are adhering to the supposed Jesuit maxim : …give me the child for the first seven years and I will give you the man…..
I applaud Mr Gutmann but Iam appalled that it should come to this. This Woke movement is innately stupid, being unable to see that it represents a most illiberal, racist body of people all proclaiming their egalitarian credentials…….irony does not begin to describe this…..
The next hurdle of course will be what University will these well educated young people attend. I cannot imagine a university that would accept them unless they were prepared to conform…….
Due to their lack of achievement, complete reliance on White people, and their own general unattractiveness, only blacks are racist. Only blacks could be.