Barack and Winston: both going all the way for Mom

The visit of Barack Obama to London, Berlin and the Middle East has given us all a better chance to consider at closer range whether he is the real deal, weather he is as good as he seems. In weighing him up, may I suggest that we consider a key character off stage whose presence is increasingly being felt; Obama's mother, Stanley Ann Dunham, who died 13 years ago.

Obama rarely invokes his mother's spirit on the campaign trail. But, asked recently to choose one prized keepsake, he said his was a photograph of the cliffs in Hawaii where his mother's ashes were scattered.

In Dreams from My Father: A Story of Race and Inheritance, his youthful autobiography, he writes: "She was the single constant in my life, the kindest, most generous spirit I have ever known ... What is best in me I owe to her." It's a generous tribute. And in a recent Father's Day speech he told her story as a single mother who "struggled at times to pay the bills, to give us the things that other kids had; to play all the roles that both parents are supposed to play".

Yet, although every sentence that he utters is carefully analysed, as is John McCain's, no one has pointed out the similarities that exist between the ambitious mothers of Barack Obama and Winston Churchill as crucial formative influences propelling their sons towards political leadership.

Just as Winston Churchill's mother, Jennie Jerome, instilled in her adolescent son a belief in his destiny to lead his country, so did Stanley Ann Dunham – the first name was her father's choice as he wanted a boy, although she was known as Ann. She was always, according to Obama, "so earnest, so certain of her son's destiny. The idea that my survival depended on luck remained a heresy to her".

Both sons were unusually close to their mothers, even when physically apart. In Obama's case this often happened, as Ann travelled to remote villages in Asia for lengthy periods during her time as an anthropologist. Both boys began life with a longer than average period of maternal bonding as a much-loved, only child. Winston was six when his younger brother, Jack, was born; Barack was nine when a half-sister, Maya, was born after his mother married, for the second time, an Indonesian named Lolo Soetoro.

Yet neither woman lived to see her son triumph. Jennie died in 1921, aged 67, following a fall and subsequent haemorrhage; Obama's mother died from ovarian cancer in 1995, aged 53.

The parallels don't end there. Both Jennie and Ann were young, sexually confident mothers. Jennie was 19 when she agreed to marry the then 24-year-old Lord Randolph Churchill; Ann was 18 when she married. Brooklyn-born Jennie had been taken to Europe by her ambitious mother. Ann, although born in Kansas, grew up in Hawaii where her white parents had moved, in part because they were appalled with the prejudice they encountered. At the University of Hawaii, Ann met and quickly fell for an African scholarship student, Barack Obama Snr, some years older than she was, who already had a wife in Kenya.

Even the weddings share some characteristics. None of the parents was thrilled. Obama tactfully draws a veil over this event in his memoirs, saying "how and when it actually occurred is a bit murky: there's no record of a real wedding, a cake, a ring, a giving away of the bride, no families in attendance". Similarly, Jennie's future in-laws, the Duke and Duchess of Marlborough, were deeply unhappy with their son's choice of bride, and did not attend the 1874 wedding in Paris.

Winston, born seven and a half months later, spoke in later life about his birth, joking that, although he was present on that occasion, he had "no clear recollection of the events leading up to it". Recently, however, evidence has emerged which makes clear that Jennie's overwhelming confidence had persuaded her to meet Randolph in his hotel bedroom two months before the wedding. She was, it now seems certain, already pregnant at the time of the wedding.

Stanley Ann Dunham also knew her own mind. For a white woman from Kansas to be married to a black man from Kenya required courage in 1960s America. Friends have described her as a big thinker who cared about global issues and embraced difference.

Compare both women's attitudes to their sons' education. In 1967, Ann moved to Indonesia. Since there was not enough money for Barack to attend the International School in Jakarta, his mother now took upon herself the burden of supplementing her son's education while he attended first a Catholic, then a predominantly Muslim school. Five days a week, she came in to his room at four in the morning, "force fed me breakfast and proceeded to teach me my English lessons for three hours before I left for school and she went to work", Obama recounts in his memoirs. However hard he tried to resist, she would patiently repeat her most powerful defence: that this was no picnic for her either.

In 1892, Jennie organised a trip to Paris for the 17-year-old Winston to improve his French. He was outraged, making as much fuss as if he were being sent to Australia for two years, according to Jennie. Yet Jennie, like Ann, won the argument. She told him: "Frankly ... I am going to decide and not you!" Three years later, when Lord Randolph died and there was no money for Winston to attend university, Jennie, acting as a tutor, sent her son a constant stream of books including Henry Fawcett's Manual of Political Economy, Gibbon's The History of the Decline and Fall of the Roman Empire and Plato's Republic.

Just as Jennie wrote to Winston, telling him he must work harder if he was ever to achieve anything in the world – "for a man, life means work if he means to succeed" – so Ann reminded her son about the need for effort. "Damn it, Bar," she is quoted as telling him, "you can't just sit around like some good-time Charlie waiting for good luck to see you through." Both mothers struggled at times to earn a living. Jennie, in an era when women weren't trained or expected to earn their own living, nonetheless tried various ventures until finally she discovered interior decorating – before the profession had a name. Obama's mother worked as a consultant for the United States Agency for International Development and for the Ford Foundation, championing the rights of women and helping to set up micro-credit programmes for the poor.

Both Barack and Winston did their best to help out when times were hard. When Ann separated from her second husband and returned to further education, her student grants had to support three people. The fridge was often empty. "I did my best to help her out where I could, shopping for groceries, doing the laundry, looking after the knowing, dark-eyed child that my sister had become," Obama wrote. Similarly after Randolph died, when Winston went to America on his first lecture tour, he sent Jennie a cheque for £300, explaining that "in a certain sense it belongs to you, for I could never have earned it had you not transmitted the wit and energy which are necessary". Jennie also remarried, but her second husband's contribution to the family income was never enough.

Obama's parents divorced when he was two and he saw his father only once afterwards; he was 21 when his father was killed in a road accident. Winston was 20 when Lord Randolph died, but there had been little contact before that. Yet another shared filial characteristic is that, in spite of an absent father, both men entered adult life seeking approval from their missing fathers. It is no coincidence that Obama entitled his book Dreams from My Father. "Even in his absence his strong image has given me some bulwark on which to grow up, an image to live up to or disappoint." Winston, in 1947, wrote a short story, later called The Dream, in which he outlined world events to the man he worshipped – his father.

Of course, mothers and sons tend to be close, but with Winston Churchill and Barack Obama, there was something remarkable. That both were able to retain their mothers' unconditional love, however hard they pushed, demonstrates in both cases the iron strength of their bond. Learning how far to push, and still carry with you those who love and support you, are basic leadership skills. The influence of a strong, single, suffering mother pushing a first-born son to believe in his own destiny is a powerful image. It's tempting to interpret the resulting drive to political leadership as a desire – since they can do no more to alleviate their mothers' situation – to put the whole world to rights, no less.

Anne Sebba is the author of 'Jennie Churchill: Winston's American Mother' (John Murray, £25)