Forty Ways to Look at Winston Churchill is an unconventional biography. Why did you write it the way you did? 

Forty Ways to Look at Winston Churchill is like a dozen biographies rolled into one. Rather than detail the facts of Churchill’s life, as most biographies do – which can make them so long and dense that a reader loses the big picture – Forty Ways answers essential questions (essential, to be sure, in my view). What was Churchill’s decisive moment? What was his greatest strength? Was he an alcoholic, did he suffer from depression, did he have a happy marriage?

Forty Ways also demonstrates the limits of biography – it’s written in a way that reveals the impossibility of presenting a single, objective portrait of Churchill. A biographer could emphasize that Churchill loved guns and fighting, and once wrote a letter to his mother bragging about shooting several men dead in the face. Or a biographer could emphasize that Churchill wore pale pink silk underwear, loved to recite poetry, and cried frequently. Forty Ways conveys the debate over Churchill’s character and accomplishments, and allows readers to judge.

The attempt to distill Churchill’s life underscores that there is the truth of facts, and there is the truth of truth. The truth we remember is shaped by our need for coherence, for which we employ artistic devices: selection, emphasis, irony, foreshadowing, metonymy, theme, allusion. This artifice is how we attempt to grasp the truth.

So would you say that Forty Ways is much about the nature of biography as about the life of Churchill? 

Absolutely.

One of the unusual aspects of Forty Ways is that you present different portraits of Churchill – some heroic, some critical – while most biographies present a single point of view. Why? 

As I researched Churchill’s life, I was struck to see his biographers reach different conclusions from the same facts. Churchill was a military genius – or a meddling amateur. He was a great defender of liberty – or reactionary imperialist.

Once I had command of the material, I amused myself by tracing how each account exaggerated certain details, and slid over others, to support its conclusions. To make sense of the conflicting evidence, and to establish what I thought important, I decided to write a biography of my Churchill.

But instead of presenting the facts to support my conclusion, I decided to show the counter-arguments as well. So while many biographies disguise or reconcile conflicting views, I highlight them. I present Churchill in all his virtues and flaws; his humor and his pomposity; his inspired strategies and oddball notions.

How did you get the idea to present both sides together? 

I’d seen this before. When I was clerking for Justice Sandra Day O’Connor at the Supreme Court, I’d often had the jarring experience of reading a convincing legal brief – and then reading an equally compelling opposing brief. Each side could marshal facts, quotes, and precedent to support opposite conclusions.

In the same way, after reading a good biography, you think you really understand its subject. But if you read several biographies about the same person, you detect the machinations of the biographers and the limits of their knowledge.

Facts can be put together to create very different portraits of the same subject. Take me, as an example. I could emphasize that at Yale Law School, I was Editor-in-Chief of the Yale Law Journal, won a writing prize, and met my future husband. I could mention that my last book, Power Money Fame Sex: A User’s Guide received a starred review from Publishers Weekly and was featured in media ranging from the New Yorker to theToday Show to the Daily News to the Howard Stern Show. I clerked for Supreme Court Justice Sandra Day O’Connor, was a chief adviser to Federal Communications Commission Chairman Reed Hundt, and my father-in-law is Robert Rubin, the former Treasury Secretary.

Or I could paint a very different picture of myself. I could emphasize that after law school, I worked only briefly as a lawyer, and then despite the huge investment of money and effort, abandoned that field to turn my efforts to writing – at a point when I’d already written two dreadful novels I’d abandoned. I failed a national math exam, wasn’t involved in a single extracurricular activity in college, and didn’t have my first boyfriend until I was twenty-three years old. I’m legally blind, left-handed, completely uncoordinated, a constant hair-twister, and afraid to drive.

All these facts are true. They leave very different impressions.

Did you hesitate to tackle a weighty subject like Churchill – given that you’re not a professional historian?

Not at all. This biography doesn’t seek to rival the works of professional historians – after all, there’s no pressing need for another scholarly Churchill biography. This book aims instead to present a personal view of a great man. I’ve written about the aspects of Churchill’s life and character that struck me as most interesting and significant, and put them into an engaging form. I also set myself the challenge of writing a short book – not easy with a subject like Churchill.

My chief interest as a writer is human character. I wrote about Churchill because I wanted to understand him. What were the nature of his gifts and accomplishments? How did he manage to achieve what he did? What shaped him and his vision? Also, I also wanted to play with the limits and conventions of biography. We’re enthralled by biography, after all, because we want to understand a particular character’s nature, and how time and circumstances alter it. I wanted to show how biographers create the very characters they memorialize.

My goal wasn’t to uncover some new fact about Churchill’s intensively researched life. After all, already in 1950, Churchill said of his life to one biographer, “There’s nothing much in that field left unploughed.” Instead, I wanted to make sense of the facts that are already known. In Churchill’s case, the staggering volume of information about him can make it hard to grasp the grand themes of his life. I wanted to highlight new aspects of the facts and also to explore the way we use the devices of fiction to understand facts of a life. I owe a huge debt to the biographers, diarists, and memoirists whose massive labors made my kind of book possible·I had so many wonderful sources to draw upon.

You’re not the typical Churchill biographer. 

No, I’m not. Churchill’s other biographers lived at the same time as Churchill, but I’m of a different generation, and was born after he’d died. That gives me a fresh perspective. I’m different in other ways, too – most of his biographers are British, and as far as I can tell, they’re all men, except for a few friends and relatives. I’m an American and a woman. The fact that I’m not a typical Churchill biographer (British, with a background in British political history or military history) demonstrates how compelling Churchill is. You don’t need to be a History Channel addict to be fascinated by Churchill. Anyone who learns the slightest bit about him will be enthralled – exactly as I was, when I turned my attention to Churchill.

Is Forty Ways intended for people who know a lot about Churchill, or for people who don’t know much about him? 

Those familiar with Churchill’s life will find fresh insights and material in Forty Ways. Also, because Churchill aficionados have their own views, they’ll enjoy the book’s shifting viewpoint – they’ll find much to agree and disagree with.

Those who don’t know much about Churchill can be daunted by the long, often multi-volume, Churchill biographies that cover every episode in his ninety years. Forty Waysfocuses on key aspects of Churchill’s character and career, and plays with the limits of biography to capture, in a one volume, the controversy, wit, and high adventure of Churchill’s life. In either case, readers will put down this book feeling as though they’ve read not one biography, but a dozen.

Was there anything you found in your research that particularly surprised or moved you? 

I found a huge amount of extraordinary material – but one quote does stand out in my memory. Doing research in October 2001, I noticed that on September 11, 1940, Churchill gave a broadcast about the “Blitz,” the brutal nightly bombing of London. At this time, New York City, where I live, was reeling from the devastation of the World Trade Center attacks, which had happened just a month before. Our city had been changed forever – and the most striking thing after September 11th was the tremendous morale and determination of the people in the city.

Churchill’s words seemed to have been written for our own circumstances. All that was needed was to substitute “New York” for “London” and “Osama bin Laden” for “Hitler.”

These cruel, wanton, indiscriminate bombings of London are, of course, a part of Hitler’s invasion plans. He hopes, by killing large numbers of civilians, and women and children, that he will terrorise and cow the people of this mighty imperial city, and make them a burden and anxiety to the Government·Little does he know the spirit of the British nation, or the tough fibre of the Londoners·who have been bred to value freedom far above their lives. This wicked man, the repository and embodiment of many forms of soul-destroying hatred, this monstrous product of former wrongs and shame, has now resolved to try to break our famous Island race by a process of indiscriminate slaughter and destruction. What he has done is to kindle a fire in British hearts, here and all over the world, which will glow long after all traces of the conflagration he has caused in London have been removed.

Why don’t we seem to have leaders of Churchill’s stature and accomplishments anymore?
Great leaders are made by great exigencies. That was true even of Churchill, with all his tremendous gifts – as Hitler pointed this out, “had this war not come, who would speak of Churchill?” We’ve been fortunate, in recent decades, not to have suffered the exigencies that produce great leaders.

Also, there’s a saying, “No man is a hero to his valet.” The valet, having seen the great man in the unsplendid context of his private life, can’t view him as a hero. Today, we’re all in the position of valets. We know far too much about great figures – about their sex lives, their weaknesses, their offhand remarks, their medical reports. This keeps them from seeming magnificent.

I think there’s something else, as well. We’re unrealistic in our expectations for leaders. We want our heroes to possess contradictory traits. We want to see confidence without arrogance, concentration without selfishness, super-human effort matched to regular habits. But virtues and vices go together. For example, the very nature that makes a person charismatic – with a desire to connect with people, to inspire, to lead – also tends to make that person promiscuous or domineering.

If you were to tackle other subjects in the same way as Churchill, whom would you choose to do? 
John F. Kennedy – I would love to write Forty Ways to Look at JFK. Also Richard Nixon.

Your last book was Power Money Fame Sex: A User’s Guide. How did you happen to write two such different books? 
To me, the two books are closely related, because they both explore my chief interest, human nature. In Power Money Fame Sex, I explored how those passions drive behavior and shape character. It was while researching “charisma” for Power Money Fame Sex that I became curious to learn more about Churchill. I’d already had my interest piqued by a World War II history, and when I read his wonderful memoir My Early Life, I became obsessed with Churchill. What a man! What a life! It became my next project.

Have you started working on your next book? 
Yes, an idea I love, a book called The Happiness Project. As in my last two books, I’m exploring an aspect of human nature – in this case, happiness.

The Happiness Project will be a memoir of a year I spend trying to be a better, happier person. Each month, I’ll tackle a different aspect of life (January might be devoted to marriage and family, for example, or work and recreation) – and I’ll report on all the ways in which I try to improve. I’m gathering rules for living from everywhere I can: from Aristotle to Thoreau to Julie Morgenstern to my friends. I’ll explain what works and what doesn’t – and whether I end my year more virtuous and happy.