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Greatness: Reagan, Churchill, and the Making of Extraordinary Leaders

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The incredible unexplored connections between two of history’s greatest leaders

Ronald Reagan and Winston Churchill were true giants of the twentieth century, but somehow historians have failed to notice the many similarities between these extraordinary leaders. Until now.

In Greatness , Steven F. Hayward—who has written acclaimed studies of both Reagan and Churchill—goes beneath the superficial differences to uncover the remarkable (and remarkably important) parallels between the two statesmen. In exploring these connections, Hayward shines a light on the nature of political genius and the timeless aspects of statesmanship—critical lessons in this or any age.

A swift-moving and original book, Greatness

• The striking similarities between Reagan’s and Churchill’s political the two were of the same mind on national defense, the economy, and many other critical issues

• What made both Reagan and Churchill so effective in the public arena—including their shared gift for clearly communicating their messages to the people

• The connecting thread of the Cold War, which was bookended by Churchill’s “Iron Curtain” address of 1946 and Reagan’s “Tear Down This Wall” speech of 1987

• The odd coincidences that mark everything from their childhoods to their shifts from Left to Right to their shared sense of personal and national destiny

Ultimately, Hayward shows, the examples of Churchill and Reagan teach us what is most decisive about political leadership at the highest level—namely, character, insight, imagination, and will. Greatness also serves as a sharp rebuke to contemporary historians who dismiss notions of greatness and the power of individuals to shape history. Hayward demonstrates that the British historian Geoffrey Elton had it right when he wrote, “When I meet a historian who cannot think that there have been great men, great men moreover in politics, I feel myself in the presence of a bad historian.”

208 pages, Hardcover

First published October 4, 2005

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Steven F. Hayward

24 books21 followers

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Displaying 1 - 15 of 15 reviews
Profile Image for Tommy.
7 reviews
June 3, 2010
I enjoyed this book for two reasons, One is the encouragement of realizing that Greatness is not the latest “spin” but rather has to do with the character of the man or woman.

“What is greatness… understanding of Aristotle , … as the ability to translate wisdom into action on behalf of the public good… To be able to do this, Aristotle argued, requires a combination of moral virtue, practical wisdom, and public-spiritedness.” (p. 17)

“Why were Churchill and Reagan virtually alone among their contemporaries in their particular insights and resolves? The answer must be that they transcended their environments and transformed their circumstances as only great men can do, and thereby bent history to their will.” (pp. 167-8)

Second is the importance of communicating Hope and Purpose. As you read Dr. Hayward’s comments about both Reagan and Churchill I found myself reflecting upon the quotes from both men (that are found on almost every page). They both had the ability to raise the awareness of their audience to see the greater good in what we can do. Life is not about the daily activities that so abundantly fill our planners but what we do with the time that we are given.

Can Greatness still be achieved…

“Can there be another Churchill, or another Reagan? The answer is plainly yes, though we must note that the greatness of statesman is seldom recognized in their our time. Typically we only recognize greatness in hindsight.” (p. 168)
Profile Image for Dave Franklin.
306 reviews1 follower
July 25, 2024
Steven Hayward’s “Greatness” examines the leadership of Ronald Reagan and Sir Winston Churchill, and makes the case that they were the true giants of the twentieth century. Hayward, a fellow at the Pacific Research Institute, compared these epic figures in this extended essay, and returns the reader to the world of Aristotle. For Aristotle, political greatness is the ability to translate wisdom into action for the public good, and it entails moral virtue, practical wisdom, as well as public-spiritedness.

The author points out that contemporary political science is consumed by metrics and reductionism; hence, it seldom concerns itself with questions about human nature or greatness.The author argues that both Churchill and Reagan believed that the differences between liberty and tyranny were real and important. Following his mentor Harry Jaffa, Hayward takes a Straussian view of political science. The Straussian objection to the state of the social sciences rests on their Weberian claim that science cannot establish a valid basis to render value judgments and that the nature of human thought is largely historical. The result is relativism and nihilism; in short, the total crisis of modernity.Thus, contemporary social scientists were uncomfortable labeling Hitler's Germany or Stalin's Soviet Union tyrannies without violating their strictures to refrain from value-judgments.

The comparison between Reagan and Churchill is apt, while they were very different men, in distinctive nations, who faced contrasting circumstances, they had much in common. Both men were facile writers: Churchill was an accomplished historian, and Reagan wrote thousands and thousands of pages for radio addresses and columns which kept him in the public discussion during the seventies. Reagan's wit and humor was comparable to Churchill's. Both men changed political parties, and obsessed about the importance of the spoken word. Conservatives, they both made unpopular distinctions and frequently received the opprobrium of the media:regardless, they maintained their joie de vie.
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“Greatness” captures the essence of these two lions. In all likelihood, they will grow in the esteem of historians.Hayward’s book is well documented and ripe with pithy quotations.The author lets his subjects speak, and we are stirred. Churchill was instrumental in defeating Nazism; Reagan in defeating communism, two monstrous tyrannies. While they were very different, they shared greatness. Hayward has given us a gift.
Profile Image for Lizz Trotsyuk.
31 reviews
March 24, 2025
This was a quick and enjoyable read that provoked my thoughts about what it means to be a true statesman. After studying this concept throughout my semester, I find that this book challenged my thinking and forced me to refine my definition of a statesman. We ought not to confuse “mediocrity for true greatness.”

I found that the author did a good job of conveying the information in a clear and concise manner. Compared to the last book I read, this was a breath of fresh air. The comparison between Reagan and Churchill was interesting to examine and helped me refine what the characteristics of a true statesman are. Overall, a pleasant and easy read that I’d recommend to others!
Profile Image for John.
1,185 reviews12 followers
June 3, 2017
A fan of both. Both were great for history. The author was well informed and really projected that.
3 reviews
July 11, 2018
Wonderful insights as to what makes a great leader, great example quotes and history.
Profile Image for Graham Bradley.
Author 24 books43 followers
August 12, 2018
Interesting comparison between the two men, their mannerisms, how they bucked convention in their time, and what can be learned from it.
Profile Image for Randy.
136 reviews13 followers
August 6, 2011
Can greatness among human beings really be spoken of in modern times? Perhaps it is a politically incorrect, anachronistic idea in our egalitarian age. Indeed, regarding both these men, Churchill and Reagan, the media appears to have downplayed their legacies for just this reason. For example, Time magazine in 1950 named Winston Churchill "Man of the Half-Century" but passed him over at century's end for "Person of the Century", explaining that "...Churchill turned out to be a romantic refugee from a previous era who ended up on the wrong side of history." And Reagan? The news media, which had consistently downplayed him during his presidency, was astonished by the outpouring of public sentiment at his death in 2004 as this showed in spades the esteem in which he was held.



Certainly the verdict of history is not passed immediately on the legacy of statesman; it takes time. Who would have thought in the 1980's, that the name of Ronald Reagan would be uttered in the same sentence as that of Winston Churchill, less than twenty years after the former had left public office? The idea that Churchill was a great man, though not agreed upon by everybody, still seems to be more easily embraced than the idea that Reagan was. But our response to Reagan's death, one of looking back and re-assessing his legacy, surprises us at the warmth we feel for the man. I don't need to read an essay to feel it in my bones that there was something special about Ronald Reagan. Steven Hayward (the author) gives some insights into explaining what many of us already believe to be true. He spends most of the 170 page book comparing both men, demonstrating the surprising number of similarities that they had, from their childhoods, to their early liberal inclinations, to their switch to conservative political views, and to how they were perceived at the time. Certainly a common perception of Reagan during his presidency was that he was "uninformed, even ignorant, and relied on simplistic platitudes to get by." But some of Churchill's top aides said the same thing, that Churchill "has only half the picture in his mind, talks absurdities, and makes my blood boil to listen to his nonsense" (Field Marshall Alanbrooke). This is just one of many, many parallels that are listed. We remember that Reagan was charged with being a warmonger. So was Churchill. He alienated himself from many in his own party during the 1930s for his strident warnings of German fascism. In fact, Churchill's "Iron Curtain" speech in 1946 was not received very well and his own government made a point of distancing itself from it. Forty years later, Reagan's "tear down this wall" speech at the Berlin Wall had his own aides fearing that he would only embarrass himself. Even after Reagan's presidency, when the Berlin Wall had in fact come down, and the Soviet Union was no more, some felt that the credit belonged to Gorbachev. Time magazine, in fact, named Gorbachev "person of the decade" in 1990. But I think it is appropriate to ask for Gorbachev's assessment, since his early opinion of Reagan was far from flattering. His presence at Reagan's funeral in 2004, seated next to Margaret Thatcher reinforced his words in 2002 that "I am not sure what happened would have happened had he (Reagan) not been there."



In his Iron Curtain speech Churchill said that World War II could have been prevented "without the firing of a single shot." According to Margaret Thatcher, Reagan brought the cold war to an end "without firing a single shot." Both men believed in peace through strength. Both men doggedly spoke their minds and followed convictions that had not only their political adversaries, but also those in their own party, scratching their heads. Especially regarding what they considered the evil of communism, both men stood alone at times, but history has vindicated them. They were far from perfect, but how many great men are? Arriving at a conclusion of greatness is made even more difficult when the concept of greatness itself in the modern world is called into question. Steven Hayward has done a masterful job of not only allowing us the possibility of considering greatness abstractly, but of applying it to these two remarkable men.
7 reviews
January 24, 2008
Probably because I am a fan of men who own the great ideas of history I enjoyed this read greatly. Extraordinary leadership is a genuine blessing and we often do not recognize it until after it has left the scene. This book is a quick read and stimulates the imagination on the topic of which qualities construct the nature of such leaders.
Profile Image for Daniel.
Author 1 book7 followers
April 18, 2015
less of a focus on specific polices, but rather a compare and contrasting of the two men, and how their lives were shaped. Interesting parts comparing how each politician had unique attributes based on their life experience, that they were able to apply while in positions of President and Prime Minister.
6 reviews2 followers
November 3, 2009
somewhat interesting read but i thought the topic was poorly explored and presented. he never really gets to the "kernel" of greatness (i.e.- what it is) and spends a very short amount of focused time on exploring achieving greatness.
Profile Image for JD.
12 reviews
May 24, 2007
Communication is everything with regards to advancing your position. It's not the words, it's the vision the listener leaves with and takes away.
Profile Image for John.
12 reviews
December 4, 2007
Very interesting comparison. I think history will eventually put Ronald Reagan in the same esteem with Winston Churchill.
Profile Image for Brenden.
189 reviews9 followers
Read
January 18, 2010
Greatness: Reagan, Churchill, and the Making of Extraordinary Leaders by Steven F. Hayward (2005)
Profile Image for Joe.
74 reviews11 followers
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June 23, 2012
Mentioned in Fred Barnes' June 2012 article in The Weekly Standard.
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