Elchanan Poupko

Devarim: Churchill’s Loneliness

Churchill, Winston Winston Churchill. FSA-Office of War Information Collection/Library of Congress, Washington, D.C. (LC-USW33-019093-C) Source: Wikicommons
Churchill, Winston Winston Churchill. FSA-Office of War Information Collection/Library of Congress, Washington, D.C. (LC-USW33-019093-C) Source: Wikicommons

Leadership is the other side of the coin of loneliness, and he who is a leader must always act alone. And in acting alone, accept everything alone. (Ferdinand Marcos)

If there is one theme that threads through the life and legacy of Winston Churchill, it is not his leadership, as much as his loneliness. Sure, there were countless times Churchill found himself surrounded by admiring crowds and eager supporters, yet through much of his life, Churchill was a lonely outsider. In the year 1900, Churchill was elected to the British Parliament as a conservative. In 1904, he defected to join the liberals. In his years in Parliament, Churchill represented Manchester, where he befriended a chemist named Chaim Weitzman, a friendship that lasted decades and helped make Churchill into an ardent Zionist, a position that was not always politically expedient.

During World War I, Churchill oversaw the Gallipoli campaign which ended up in a disaster, leading to his resignation from his government position.

In 1921 Churchill was appointed as Secretary of State for the Colonies. After visiting the Holy Land and the Arab violence and opposition to Jews living there, Churchill gave a stirring speech in Parliament in support of building a Jewish homeland in Israel for the Jews, a position that put him on the outs in many political circles.

There were many other lonely moments, such as losing his seat in Parliament in 1923, or what Churchill himself has called his “desert years”, alone at home, for many of the 1930s, yet nothing made Churchill as lonely and as popular as his brave stance against Adolf Hitler.

In 1938, as Prime Minister Neville Chamberlain kept to his appeasement policy towards Hitler, Churchill became a fierce voice of opposition. That March, the Evening Standard, which used to publish Churchill’s columns, stopped publishing them. In May 1940, Churchill became prime minister of England and started heading a strong opposition to the Nazi regime. With scarce allies and much determination, Churchill began his fierce leadership in England’s “darkest hour.” He led with courage, wisdom, tact, foresight, and even humor—to a resounding victory. The rest can fill shelves and rooms of history books. What is less known is that shortly after the war, Churchill was voted out of office. He could not believe it. Once again, Churchill was alone, perhaps, even lonely.


Churchill was not the first lonely leader.

Leadership and loneliness have gone together thousands of years before Churchill.

In this week’s Parsha in recounting his years as their leader, Moses famously tells the Israelites:

“And I said to you at that time, saying, ‘I cannot carry you alone…How can I bear your trouble, your burden, and your strife all by myself?”

These latter words are often most remembered since they are read in the same tune as the book of Lamentations, on Tisha Be’ Av, the day we mourn the destruction of both temples; “eicha esa levadi” here, so similar to “eicha yashva badad—how did she sit in solitude” (Lamentations 1)

Moses, the great—in fact, the most exceptional leader—feels like he can no longer do this alone.

Rashi, the great French medieval commentator, cites a rabbinic teaching shocked by our great leader’s frustration:

“I cannot alone— Is it possible that Moses could not judge Israel? The man who brought them out of Egypt, split the sea for them, brought down the Manna, and caused the quails to fly, could not judge them?”

The rabbis could not fathom the notion that Moses would not be able to do this alone; it defied logic that Moses—with his record of leadership—would throw up his hands and give up on the Jewish people. So what did Moses mean if not to give up?

“Rather, he said to them, “The Lord, your God, has multiplied you” – [i.e.,] He has made you superior and elevated you higher than your judges. He took the punishment away from you and imposed it upon the judges [in cases where they could have prevented your wrongdoing and did not]. Solomon made a similar statement: “For who is able to judge Your great people?” (I Kings 3:9) Is it possible that he [i. e., Solomon] of whom it is said (I Kings 5:11), “He was wiser than all men,” could say, “Who is able to judge?” But this is what Solomon meant, The judges of this people are not like the judges of other peoples, for if [one of the judges of other nations] gives judgment and sentences a person to death, to lashes, or to strangulation, or perverts judgment and robs him, it means nothing to that judge; if, however, I cause a person to pay unjustly, I am liable with my life, as it is said (Proverbs 22:23), “And He robs the life of those who rob them” (Sifrei, San. 7a)”

This commentary blends two answers given in the Midrash as per why Moses felt lonely and unable to tend to the Israelites: the growing number of the Jewish people as well as the profound sense of responsibility for the outcome of his judicial verdicts.

And yet, the term “eicha—how can I?!” is used here in a much broader context. We read it the same way we read the words lamenting the very destruction of our sovereign and sacred city, “eicha yashva badad” how has she—Jerusalem—come to sit all alone. The word eicha embodies a mixture of a question, disbelief, shock, and lamentation. This word, with a magnitude thunders its painful cry through our history, is the word Moses uses to describe his sense of loneliness.


So what was it all about?

Rabbi Naftali Zvi Yehuda Berlin, known as the Netziv (1816-1893), was one of Lithuania’s most respected scholars. In his commentary on the Torah, he explains that when the Torah says, “The Lord, your God, has multiplied you,” it is not just talking about numbers, it is talking about opinions. While complaining and quarreling were common when leaving Egypt, after forty years in the desert, it just got worse. Moses realized that his authority over a second generation will not be the same as his leadership to the first-generation. In fact, his authority towards a people – now a year away from slavery – will never be the same as his leadership in the first year after leaving. Moses is happy to lead and get things done; he is not happy to negotiate with and please each and every disputing individual.

Commentaries draw this moment of loneliness to the time the Israelites complained about the Manna and demanded to eat meat (Numbers 11:16). Others point to the time Yitro (Exodus 18) told Moses he could not judge the entire nation, while others give more examples. Whatever path you may take on this, leading alone, was something that Moses felt he could no longer do.

While feeling the burden of lonely can come from being overwhelmed, it can also come from a lack of that same feeling. There is a huge difference between Moses’s need for help as an overwhelmed judge and leader in the book of Exodus, and the sense of loneliness when he is shocked by the decadent demands for more meat. One is needing more resources to address essential needs, while the other is the feeling of being one too many in the leadership of a people that never cease to surprise him with their complaints. And so Moses says “eicha?!,” how can I do this on my own.

Yet the rabbis of the Hesder Yeshiva in Yerucham, Israel, point out another thing. Moses is not just lamenting a quantitative loneliness; he is also lamenting a qualitative one. He no longer feels connected to the people. A new generation of Israelites has emerged, and he no longer feels the connection to them.

It is this tone of Eicha that resonates with the same Eicha we use to lament the destruction of Jerusalem. Moses lamenting the disconnect, as we later lament our own disconnect from God and who we are.

Interestingly, in a 2012 article in the Harvard Business Review Thomas J. Saporito, writes

“Often dismissed and rarely discussed, many CEOs are plagued by feelings of isolation once they take on the top job…. half of CEOs report experiencing feelings of loneliness in their role, and of this group, 61 percent believe it hinders their performance. First-time CEOs are particularly susceptible to this isolation.”

With leadership comes loneliness. Doing the right thing, will often put us at odds with others. It is our task as leaders in our fields, to rise to that occasion, and embrace that loneliness. Will it be easy? No. Great men like Moses had to live with it their entire life. Will there be times we will feel tired, burdened, and overwhelmed? Sure. Yet as the rabbis taught (Avot, 2:16) “It is not your duty to finish the work, but neither are you at liberty to neglect it.” With leadership comes loneliness. As we embrace tough decisions in our lives, let us remember that sometimes, with those decisions, we may find ourselves isolated or alone like Moses or Churchill, and that is ok. The pain may be harrowingly excruciating—so much so that we may cry out “eicha—how can this be?!” Yet knowing that we have delivered our people to their promised land can give us comfort and remind us that it was all worth it.

Shabbat Shalom.


About the Author
Rabbi Elchanan Poupko is a New England based eleventh-generation rabbi, teacher, and author. He has written Sacred Days on the Jewish Holidays, Poupko on the Parsha, and hundreds of articles published in five languages. He is the president of EITAN--The American Israeli Jewish Network.
Related Topics
Related Posts