“What was Churchill’s Phi­los­o­phy of Life and Liv­ing?” was first pub­lished by the Hills­dale Col­lege Churchill Project. For the orig­i­nal arti­cle with end­notes, click here. To sub­scribe to free week­ly arti­cles from Hills­dale-Churchill, click here and scroll to bot­tom. Enter your email in the box “Stay in touch with us.” No adver­tis­ing: Your iden­ti­ty remains a rid­dle wrapped in a mys­tery inside an enigma.

Q: On life and living

If I want to under­stand Sir Win­ston Churchill’s phi­los­o­phy of life and liv­ing, what books would you rec­om­mend? —B.A., via email

A: Lengthy sources

At first your ques­tion remind­ed us of the old fra­ter­ni­ty ini­ti­a­tion tech­nique: ask­ing pledges an unan­swer­able ques­tion. I remem­ber mine per­son­al­ly: “Tell us your phi­los­o­phy for liv­ing among men.” This was an inten­tion­al red her­ring. What­ev­er you answered, it obvi­ous­ly would nev­er sat­is­fy the questioner!

But in pon­der­ing the thought, there very def­i­nite­ly is a body of work that helps answer your query. Please use the Hills­dale Churchill Project’s online anno­tat­ed bib­li­og­ra­phy for details and notes on books men­tioned,  or to search for oth­ers in the same field. Search for key words like “phi­los­o­phy.”

Churchill Style by Barry Singer

The book to start with is Churchill Style: The Art of Being Win­ston Churchill. Author Bar­ry Singer owns Chartwell Book­sellers and will sell you an inscribed copy—along with copies of oth­er books below, many of them inscribed by the authors.

Churchill Style expert­ly dis­cuss­es Churchill’s phi­los­o­phy of life and how he lived it. Mr. Singer has a unique approach. He con­sid­ers nine facets of Churchill that were the essence of his style: autos, books, cig­ars, din­ing, fash­ion, friend­ships, home, imbib­ing and pas­times. (I”m glad he includ­ed cars—there are amus­ing sto­ries there.)

The pub­lish­er, Har­ry Abrams, is well known for ele­gant pro­duc­tions, so Churchill Style is an heir­loom, fine­ly print­ed and bound and laden with full col­or illus­tra­tions, includ­ing rare first edi­tions of Churchill’s books. It is a book read­ers will refer to often. Mr. Singer’s Hills­dale lec­ture on the sub­ject is acces­si­ble here.

No More Champagne by David Lough

Churchill (or his friend F.E. Smith) was known to have declared, “Win­ston is a man of sim­ple tastes. He is quite eas­i­ly sat­is­fied with the best of everything.”

With no inher­it­ed wealth, WSC had to earn enough to finance his plea­sures, remark­ing, “I lived from mouth to hand.” The stan­dard work on his finances is David Lough’s No More Cham­pagne: Churchill and His Mon­ey. Review­ing this book for Hills­dale, Michael McMe­namin wrote:

Plough­ing fresh ground, Lough offers a well-writ­ten, deeply researched text about Churchill’s finances, and how they affect­ed his pol­i­tics. As pri­vate as some may regard per­son­al finances, the book does not detract from Churchill’s great­ness or human­i­ty. It is an absorb­ing sto­ry about an extra­or­di­nary man ensur­ing his finan­cial sur­vival with one hand, while warn­ing about the dan­ger to, and then lead­ing the fight for, West­ern Civ­i­liza­tion with the oth­er. Unique­ly, Churchill did both.

Churchill’s Bestiary by Piers Brendon

Ani­mals were impor­tant in Churchill’s life. He was always sur­round­ed by pets—or, at least, ani­mals he thought of as pets. He was fierce­ly loy­al to those he “knew per­son­al­ly,” and liked to use ani­mal analo­gies in his speech­es. For­tu­nate­ly for stu­dents of his life, 2019 brought us a com­pre­hen­sive book devot­ed to the sub­ject: Piers Brendon’s Churchill’s Bes­tiary reviewed here. From my review:

This is an ency­clo­pe­dic account of Churchill’s life with ani­mals, start­ing with “Alba­tross” and end­ing in “Zoos.” That spans only a frac­tion of Piers Brendon’s com­pre­hen­sive book. He avoids repeat­ing mate­r­i­al in pre­vi­ous accounts, and goes much deep­er into the subject.

Most of the anec­dotes have not appeared pre­vi­ous­ly and are thus quite valu­able. Mr. Bren­don deeply inves­ti­gates each species. The text is spright­ly and read­able, “unput­down­able.” Any­one inter­est­ed in this aspect of Churchill’s life owes it to them­selves to buy a copy.

In his own words

For Sir Winston’s own com­ments on his phi­los­o­phy of life, see the chap­ters “Per­son­al Mat­ters” and “Tastes and Favorites” in my book, Churchill by Him­self aka Churchill in His Own Words. Here are quo­ta­tions relat­ing to Churchill per­son­al­ly: his char­ac­ter, habits and fam­i­ly, and his pre­scrip­tions for liv­ing life to the full, which he cer­tain­ly did.

Many quo­ta­tions speak to his polit­i­cal and per­son­al char­ac­ter­is­tics, some with a high degree of frank­ness. Reac­tions to elec­tion results, and thoughts about his being var­i­ous­ly a Con­ser­v­a­tive and a Lib­er­al, are pithy and point­ed. Of course his domes­tic exis­tence always came sec­ond after pol­i­tics. But fam­i­ly life was a rous­ing, warm affair, except for his occa­sion­al­ly tem­pes­tu­ous rela­tion­ship with his son Ran­dolph.

WSC’s com­ments to and about his wife Clemen­tine, the best of which I trust are here, would make a per­fect series of greet­ing cards for any hus­band won­der­ing how to express him­self. Their daugh­ter Mary gave tes­ti­mo­ny to her father’s favourite max­im describ­ing his mar­riage: “Here firm though all be drifting.”

What strikes me about these quo­ta­tions as a group is what one of his sec­re­taries said about Churchill: “He was so human, so funny—that always saved the day.” Mar­shal Tito, a most per­cep­tive man, was once asked what most struck him about WSC. “His human­i­ty,” Tito said imme­di­ate­ly. “He is so human.”

Philosophy of politics

If your inter­est extends to polit­i­cal life there are three chap­ters in Churchill by Him­self con­tain­ing quo­ta­tions on war and the two World Wars. Anoth­er chap­ter cov­ers “Polit­i­cal The­o­ry and Prac­tice.” Also, there are at least two pow­er­ful schol­ar­ly stud­ies of his polit­i­cal phi­los­o­phy that should be part of the seri­ous library.

Sir Mar­tin Gilbert’s Churchill’s Polit­i­cal Phi­los­o­phy (1981) is rare but worth seek­ing out. (Try bookfinder.com,) It is based on a Gilbert lec­ture which unique­ly cap­tured Churchill’s atti­tudes toward pol­i­tics and gov­ern­ment. WSC’s over­rid­ing doc­trine, Gilbert says, can be sum­ma­rized in five words: “His quar­rel was with tyranny.”

Like­wise excel­lent on polit­i­cal phi­los­o­phy is Lar­ry Arnn’s Churchill’s Tri­al: Win­ston Churchill and the Sur­vival of Free Gov­ern­ment. As a bonus, this book con­tains WSC’s essay, “Mass Effects in Mod­ern Life.” From the book review by Justin D. Lyons:

Churchill stud­ies reveal impor­tant lessons that remain pow­er­ful­ly rel­e­vant for the lead­ers and cit­i­zens of free soci­eties. This notion is itself found­ed on the belief that though the threats to civ­i­liza­tion may have altered since Churchill’s day, there is con­sis­ten­cy between his chal­lenges and ours—that he is a good guide to fol­low in the cause of defend­ing freedom.

Such a belief must lie behind any con­cep­tion of his­to­ry as pro­vid­ing guid­ance. If these com­mon­al­i­ties do not exist, nei­ther Churchill’s sto­ry, nor his­to­ry in gen­er­al, has any­thing to say to us now. This is a unique and impor­tant work on Churchill’s polit­i­cal thought.

Addenda

These books focus close­ly on your ques­tion, though we could go on nam­ing spe­cial­ized stud­ies. For exam­ple, who were the men­tors who made Churchill what he was in life? For three such indi­vid­u­als, see Michael McMenamin’s “Churchill’s Men­tors,” Part 1 of which is post­ed here, with links to two more parts.

Churchill’s life was long and occu­pies the authors of over 1200 books, not includ­ing the thir­ty-one vol­umes of Offi­cial Biog­ra­phy. Many con­tain exag­ger­a­tions, and it is well to look out for them. For just one such exam­ple see “On Churchill’s ‘Sybarit­ic’ Lifestyle” (2016).

We hope this answers your ques­tion and pro­vides at least a start on a com­pli­cat­ed but intrigu­ing subject.

“Blood, Sweat and Gears”: Churchill as Motorist

1: “Mors the Pity,” 1900s-1920s.

2: “Daim­lers and Austins,” 1930s.

3: “There’s Safe­ty in Hum­bers,” 1940s-1960s.

“Dri­ving Miss Nan­cy: Nipped in the Astor Bar,” 2022.