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Posted on Dec 5, 2008 in Carlo D'Este, War College

Churchill and Obama – Leadership Challenges in Tough Times

By Carlo D'Este

Winston Churchill in the ruins of the House of Commons debating room followng a German air raid in May 1941. Library of Congress.There is a striking parallel between the challenges faced by our new president-elect and those of Winston Churchill during World War II. Both men are assuming the mantle of leadership at a critical moment in his nation’s history. And, just as Churchill had no assurance of ever succeeding when he became prime minister in May 1940 (indeed the odds of failure were astronomically high), neither does President-elect Obama. However, where one man triumphed through sheer will and astute leadership, the other can take solace that the problems of 2008 and beyond are solvable.

One of the characteristics of Churchill’s coalition government during World War II was that the crisis trumped political differences.

And while America of the 21st century is far stronger in every way than Britain in 1940, even a robust economic recovery will not resolve the myriad problems facing this nation. Stalwart leadership will. And therein lies our best shot at emerging a stronger and more vibrant nation in the years ahead. Indeed, the lessons of history suggest that what Churchill accomplished in 1940-1941, when there was absolutely no light at the end of the proverbial tunnel, can be replicated.


During those grim years Churchill had little to offer the British nation but, as he put it a mere three days after becoming prime minister, “blood, sweat, and tears.” We face the same challenge of our own version of “blood, sweat, and tears”: a shattered economy in the worst shape since the Great Depression of the 1930s, war in two of the world’s most inhospitable places that has lasted longer than World War II, faltering education and health systems on life support, a populace divided by ideology, a government characterized by inaction in both the executive and legislative branches, and a very unstable post-9/11 world in which the prestige of the United States has sunk to an all time low.

Pulling the levers of finance and credit and formulating new initiatives will certainly help but looming largest of all is the great intangible of leadership, of restoring a global confidence in the United States, and engendering a belief that in the end things will be all right.

* * *

The president-elect can draw some valuable lessons from the example set by Churchill during Britain’s darkest hour. Despite his private feelings at times that even he could not save his nation, the new British leader did not take counsel of his fears. He exuded a combination of confidence and defiance, and used his great oratorical skills to bolster public morale. Defeat was simply not in his DNA.

What other traits of leadership did Churchill possess? He was authentic and charismatic. He made people feel good about themselves during times when there was precious little to feel good about. After the first large-scale bombardments of the London docks in September 1940, he made a point of hastening there to view fires burning amid the devastation. At an air-raid shelter where some forty people had been killed by a direct hit, Churchill found a large crowd of mostly poor people. “One might have expected them to be resentful against the authorities responsible,” recalled his military secretary, Gen. Hastings Ismay, “but as Churchill got out of his car, they literally mobbed him. ‘Good old Winnie,’ they cried. ‘We thought you’d come and see us. We can take it. Give it ‘em back.” Tears flowed down Churchill’s cheeks at the sight before him. Ismay heard an elderly women exclaim: “You see, he really cares; he’s crying.”

After France sank into the abyss of defeat and occupation, Churchill was determined to show defiance, reason, confidence, and occasionally tears. He had, in effect, “staked his own survival as Prime Minister upon a strategy of ‘no surrender,’” observed one of his ministers. Most of it was sheer bluff and intended to reassure both his colleagues and the nation. Anything less than optimism, even the slightest hint of failure, would have sent a defeatist message. Instead, Churchill spoke of “our inflexible resolve to continue the war,” and that his military and service advisors believed “there are good and reasonable hopes of final victory.” Anything less was unthinkable. His final verdict was one of promise over adversity. This was leadership of the first order.

The deck was stacked against Churchill in 1940 and had he failed, I suspect history would not have judged him too harshly for having been dealt an unwinnable hand. As he returned to the Admiralty from his audience with King George VI, after being asked to form a new coalition government the evening of May 10, 1940, the son of Lord Randolph Churchill, who once told him he would never amount to anything, was momentarily nearly overwhelmed with the enormity of the task placed squarely into his hands. His driver and bodyguard, Inspector Walter Thompson observed that: “Tears came into his eyes, and as he turned away he muttered something to himself.” Yet, despite his steely sense of purpose, Churchill was unable to completely hide the magnitude of what was now his responsibility. “God alone knows how great it is,” he quietly remarked. “I hope it is not too late. I am very much afraid that it is. But we can only do our best.” His fears were only momentary. When he arose the following morning after only a few hours of sleep, he said to his wife, Clementine, “Only Hitler can turn me out of this job.”

The challenges Churchill faced were monumental. The Netherlands, Belgium, Luxembourg and France had been invaded on May 10 and all except France would fall under the Nazi jackboot within a short time. France’s agony would last a few weeks longer but with the same dismal result. The British Expeditionary Force would be shattered and virtually all of its equipment and arms lost but its men miraculously saved to eventually fight another day. Until December 1941 Britain would stand alone.

* * *

Courtesy Harper Collins.One of the characteristics of Churchill’s coalition government during World War II was that the crisis trumped political differences. British politicians rallied to Churchill and the cause of resistance and survival – and with the eventual alliance with the United States, of winning the war. Our present crisis calls for a similar approach in which the nation’s well being takes precedence over the divisive party politics of recent years. Left or right, red or blue have no place during a national emergency. A divided America cannot possibly benefit from partisanship in moments of crisis. Which is why the British example and Churchill’s clarion calls for unity were so important.

On the basis of what has transpired since the election on November 4 there is cause for cautious optimism that the new president and his administration will be able to take the necessary steps to right the ship. If we fail to learn from history the price of failure will be disastrous. If there was ever a time when we as a nation need to rally to a common cause it is now.

ACG Magazine Extra: Read our review of Carlo D’Este’s outstanding new biography, Warlord: A Life of Winston Churchill at War, 1874-1945 in the Bookshelf department of our upcoming March issue (on sale in mid-January).


  1. Is this some sort of a joke? Obama looks a lot more like Chamberlain than Churchill.

  2. “Until December 1941 Britain would stand alone”

    Until _June_ 1941 Britain would stand alone

    Fixed it for you, The USSR is often overlooked, but contributed significantly in the struggle to free Europe from Naziism.

  3. Churchill charged with the 17th at Omdurman and personally killed a number of the enemy at close range. He was captured by and escaped from the Boers. He fought in the trenches in WWI. He wrote the History of the English Speaking People. He was First Sea Lord in WWI and WWII before he was PM.

    President Obama was a community organizer, a 2 yr senator and has written 2 autobiographies. As I live and breatheI hope he does the right thing but as I live and breathe I’m not sure he knows what it is.

  4. I have not read significant histories specific to Churchill, but I’m sure the new President would be swooning over the notion that a historian of note favorably compares the two.

    I’ve seen nothing to this point that suggests any similarities beyond the President elect’s ability to stand at the podium and deliver a rehearsed speech. We have heard the new President’s responses where he doesn’t have the benefit of the tele-prompter and his struggle to project a clear answer when he hasn’t been tutored on the question. He deserves to have a grace period, but the author has already elevated him beyond that point.
    I believe the new president would be in a perpetual stammer if he were taking Prime Ministers Questions.

  5. Comparing “The One” with Churchill is like comparing Hitler with the Pope. “The One” is more like Chamberlain, an appeaser. “The One” wants to talk with the enemies of the US (Islamofacist’s and the ilk like them). Oh by the way, I thought when “The One” was elected the world was going to like us again because the “evil” Bush was disposed of. Also Mr. Churchill was a great orator-could deliver an excellent speech without 50 plus uh’s-so distracting!

  6. I agree to compare Churchill who was one of the greatest war leaders in history to an empty suit, is quite a stretch. The experience that Churchill possessed including Lord of the Admiralty in WWI among very extensive experiences both in government and in real combat are the opposite of what Obama brings to the table. Obama shows no qualities to even make this comparison. Obama won the election that a yellow dog running as a democrat would have won. I give almost all the credit to his campaign manager and the group that started and ran his fund raising campaign which allowed him to outspend McCain 4 to 1.

  7. Some of the responses are further off base than Mr. D’Este’s blog.

    When did military service, however much it may build character, ever guarantee political success or even successful leadership as Commander-in-Chief?

    President-Elect Obama is an untested liberal politician, and I find a more apt comparison than Churchill is FDR. He was a son of privilege who had followed his cousin’s path to Undersecretary of the Navy and Governor of New York. He made costly mistakes as president, but he made many other brilliant decisions including his willingness to help defend England and lead the U.S., belately, away from isolationism. What I’m saying is FDR grew and provided needed intangibles.

    Hell, Harry Truman didn’t even want the top job.

    Let’s pray that the crucible of the presidency bestows on our our brainy and eloquent President-elect all the wisdom he has yet to acquire.

  8. LOL, In reality, it is an insult to the memory of these deceased gentlemen by making the slightest comparison between them and Obama.

    Up to this point, Obama is probably the least accomplished President-elect in this nations history. The author started this ill conceived debate and it was a foolish initation on his part. I think we should all re-visit this in November of 2010. At that point we will be able to compare Obama’s Presidency with Pres. Clinton’s. The comparisons can start there.

  9. I have to agree to compare Obama to Churchill makes no sense, unless D’Este is saying to Obama needs to learn from Churchill’s example in leading Britian from the brink of ruin. Fortunately, the problems we face today are neither new or worse than the economy of the late 1970’s, early 1980’s. Everybody wants personal freedom but will not accept the personal responsibilty that must go with it. I think the only thing Obama and his fellow Democrates have learn from history is the usual big gov’t tax and spend policies of FDR that they are doomed to repeat again. God help us.

  10. obama couldn’t be a pimple on Winton Churchill ass. The democrats just wanted someone in the white house who would do anything they wanted to push their crooked socialist agenda. I am afraid for the United States. The idiots who voted for this sorry excuse for a president do not know any better. With the current destruction obama has cause in just over a month hopefully will bring some sane voters out at the next election. If we survive that long.