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Churchill & His Personal Life

(HINT: Using your browser's pull-down menus, use the "Find in Page" function to locate the keyword or phrase you are looking for. The Numbers refer to numbers which are given in the publication Finest Hour.)

 4. How old was Churchill when he was hit by a car in New York City? 57, 1931

 10. What pony did he love to ride as a boy at Blenheim? Rob Roy

 16. What childhood toys of Churchill's are displayed at Blenheim? Lead soldiers

 22. What Noel Coward song did WSC listen to aboard HMS Prince of Wales enroute to meet with Roosevelt? Mad Dogs and Englishmen

 28. Who shone for Churchill "like the Evening Star"? His mother

 34. Who was the artist commissioned by Parliament to paint WSC's 80th Birthday portrait? Graham Sutherland

 40. What was Churchill's best subject in school? History

 46. What was the name of the Reves' villa where WSC visited? La Pausa

 52. Madame Tussaud's first Churchill appeared on his wedding day, 12 September 1908. How many effigies were there throughout his life? Seven

 58. What did Churchill call his bouts of depression? Black Dog

 64. While in Khartoum, of what did WSC's servant Scrivings die from, which might have also killed him? Food poisoning

 70. What is significant about the date of WSC's death (January 24)? It is the same date as his father died

 76. What daughter of a British Resident in India was Churchill's first serious love? Pamela Plowden

 82. Winston and his brother Jack toured the Swiss Alps in 1895. What even almost ended his career? He almost drowned in Lake Lausanne

 88. Where is Sir Winston Churchill buried? Bladon, Woodstock

 94. Name one color of Churchill's siren suits. blue, red or green

 100. Why did Churchill stipulate the exact position of his grave at Bladon? From it one has an unobstructed view of the window of the room where he was born at Blenheim.

 106. What was Clementine Churchill's maiden name? Hozier

 112. What event on Sidney Street might have injured The Home Secretary? A gunfight

 118. Where did WSC and Roosevelt first meet? Gray's Inn, London (July 29, 1918)

 124. A lottery involving WSC was instigated on the liner he took from the U.S. back to England in 1929. What was the bet? Which hat WSC would wear to the fancy dress ball

 130. What type of music was Winston's favorite? Victorian music hall songs

 136. Winston Churchill's only venture into sculpture was a bust of whom? Oscar Nemon, the sculptor

 142. What sport was Winston fond of playing as a young man? Polo

 148. Clemmie and Winston had a pet name for Randolph before and just after he was born. What was he called? The "Chumbolly"

 154. What finally got Winston's parents to visit him at school in Brighton? A serious case of pneumonia

 160. How much older was Winston than his wife Clementine? Ten years

 166. Where did Churchill first become a cigar smoker? Cuba, 1895

 172. What were the names of Clementine and Winston's children? Randolph, Diana, Sarah, Mary and Marigold (d. 1921)

 178. What was the title of WSC's last painting? "Oranges and Lemons"

 184. How many exams did WSC need to pass into Sandhurst? Three

 190. What was 28 Hyde Park Gate? The Churchill London home (from 1945)

 196. Who or what was High Hat? One of WSC's race horses

 202. What years did Churchill deem 'the happiest of my life"? His years at Admiralty House

 208. Churchill was past 40 when he began which of his many hobbies? painting

 214. "If there be any who rejoice that I [WSC] live, to that dear and excellent woman their gratitude is due," refers to whom? Mrs. Everest

 220. WSC's comment "the journey was interesting, and well worth the taking -- once" referring to what? The journey through life

 221. What made the Left regard Churchill as a conservative despite many reforms passed while he was Home Secretary? WSC's recommendation that troops be used during strikes

 226. Did WSC have any brothers or sisters? John (Jack) Strange Churchill (1880-1947) was Winston's only sibling

 232. Where is WSC's beloved nanny laid to rest? Mrs. Everest is buried in the City of London Cemetery

 238. WSC said he made the two most important decisions of his life at Blenheim. What were they? To be born and to marry

 244. Name some of WSC's favorite authors? Somerset Maugham, Rudyard Kipling, Sir Walter Scott and Robert Louis Stevenson

 250. What was WSC's nickname for his beloved nanny, Elizabeth Ann Everest? "Woomany"

 256. Before changing his mind around his 85th birthday, where had WSC wanted to be buried? Chartwell

 262. In 1943, Winston Churchill was awarded an honorary degree from what U.S. University? Harvard

 268. What was the name Churchill gave to plans for his own funeral? Operation Hope-Not (Note: Anthony Montague Browne advises that this question is incorrect, in that WSC did not know the code name for his funeral plans.)

 274. How long were Winston and Clementine married? 57 years

 280. When did Churchill collect stamps? In his youth

 286. What was the name of Churchill's architect when Chartwell was rebuilt? Philip Tilden

 292. What name did Churchill use when he exhibited his paintings in Paris in 1920? Charles Moren

 298. In 1888 a school administrator said Winston was "regular in his irregularity." Name two other faults he accused him of having. Forgetful, unpunctual and careless

 304. What sport did Churchill actively play until 1927? Polo

 310. When Winston and Jack were small boys they went to Austria on a holiday with their parents. With whom did they have tea? Prince Bismarck

 316. About how many paintings did WSC ostensibly paint? Over 500 paintings

 322. Where did Churchill toy with the idea of buying a farm and settling? He thought of buying a farm in Canada

 328. Churchill had a wonderful collection of what type of apparel? Hat collection

 334. What color were Sir Winston's eyes? Blue

 340. What was the name of Churchill's longest serving butler at Chartwell? Inches

 346. Winston's father Randolph wished him to enter which Army branch? Army Infantry

 352. What year did Winston first meet Clementine Hozier? 1904

 358. The American ambassador to Britain in 1939 doubted Britain's ability to defeat Germany. Name him. Joseph P. Kennedy

 364. What feature of the Lord Warden of the Cinque Ports uniform most appealed to Churchill? Admiral-type hat

 370. How did Churchill sign his paintings? WSC

 376. What were Winston's and Clementine's pet names for each other? Winston was 'pig' (initially 'pug') and Clementine was 'kat'

 382. Who said to WSC that if she was married to him she'd put poison in his tea, to which Winston replied, "If I were married to you I'd drink it"? Nancy Astor

 388. On which Harrow entrance exam did Churchill do so well that he was put in the top division for that subject? #000099

 394. What is the name of the room in Blenheim Palace where WSC was born? The Dean Jones Room

 400. What title did the Royal Academy bestow upon Churchill? Honorary Academician Extraordinary

 406. In 1892 Randolph Churchill had a book published. What was its title? (Not a collection of his speeches.) Men, Mines and Animals in South Africa

 412. What did Clementine do to a suffragette who was trying to push Winston in front of a train? Wacked the suffragette with her umbrella

 418. What was Churchill's most-used pseudonym when he wrote letters which appeared in the Harrovian? "Junium Junior"

 424. How much did the Churchill's pay for Chartwell in 1922? £5,000

 430. In his first year in which subject at Harrow was Winston recognized as being the best in his division? His first year in history

 436. In 1922 The Churchills bought Chartwell for £5000. How much did their benefactors arrange to pay for the house in 1946? Lord Camrose organized the purchase of Chartwell for £95,000

 442. What pseudonym did Churchill use when he recuperated in Florida in early 1942? Mr. Lobb

 448. Who was Goonie? Winston's brother Jack's wife, Lady Gwendeline Teresa Mary Bertie

 454. During what decade did Churchill do most of his paintings? Almost half of Churchill's paintings were done in the 1930s

 460. In 1946 Lord Camrose organized a group of benefactors to purchase Chartwell. How many, besides himself, provided the funds? Lord Camrose and sixteen others

 466. What was Winston's brother Jack's full name? John Strange Spencer Churchill

 472. In 1952 one of Sir Winston's relatives married Anthony Eden. Who was she and what relation? Winston's brother Jack's daughter, Clarissa, married Sir Anthony Eden in 1952

 478. How old were Winston and Clementine when they were married? Winston was 33 and Clementine was 23

 484. According to the Boer War "wanted poster," how tall was Churchill? Five-foot-eight

 490. What well-known American Civil War poem did Churchill recite to the amazement of Roosevelt when he visited him during WW2? Barbara Frietchie

 496. What were Lord Randolph's racing colors, used by WSC in India? Pink and chocolate

 501. What was the Churchill significance of the movie Royal Wedding starring Fred Astaire? Churchill's daughter Sarah danced with Fred Astaire

 508. Many Toby mugs have been made of Churchill. Which company has been making them since 1941? Royal Doulton

 514. Where did Churchill have the only opportunity to paint during WWII? Marrakesh

 520. What activity offered Churchill a diversion and some solace after the Dardanelles fiasco? Painting

 526. What was the largest fish Churchill ever caught? "Monstrous swordfish" off the coast of Catalina in 1929

 532. What is the only major government office Churchill did not hold? Foreign Secretary

 538. Winston's mother, Jennie, was accomplished on what musical instrument? Piano

 544. To his dismay, Churchill was listed under what name when he first attended Harrow? WSC was listed under the S's as Spencer Churchill

 550. What animal sketches did Winston and Clementine usually draw in their correspondence to each other? Pug dogs and pussy kats

 556. Name Winston and Clementine's ten grandchildren. Winston (Randolph & Pamela Digby); Arabella (Randolph & June Osborne); Julian, Edwina & Celia (Diana & Duncan Sandys); Nicholas, Emma, Charlotte, Jeremy & Rupert (Mary and Christopher Soames)

 562. Name the first Churchill ancestor of Sir Winston who purportedly came to America (from Dorset). Where and when did he land? John Churchill, from Dorset, is believed to have been the first Churchill to land in America, at Plymouth c. 1643

 568. In 1919 the Churchill's sold their East Sussex home "Lullenden" to what well-known general? Ian Hamilton

 574. Name three painters who influenced WSC. John & Hazel Lavery, John Singer Sargent, Walter Sickert, and Paul Maze

 580. Churchill's brother Jack and his wife 'Goonie' had three children; name them. Gwendeline and John (Jack) Churchill had three children: John George (1909), Henry Winston (Peregrine) (1913), and Ann Clarissa (1920)

 586. How many generations back was Churchill's American Indian connection? Churchill's great great grandmother was an American Indian

 592. Winston had the lake at Sandhurst dredged in order to find what item? The pocket watch his father gave him

 598. What characteristics of Winston did Clementine Hozier say eventually won her over? Winston's "dominating charm and brilliancy"

 604. As a school boy at Harrow, what did Winston request of his father in order to increase his pocket money? His father's autographs

 610. What was "Mr. Churchill's Private War"? Concern over the Bolshevik victory in Russia

 616. At what age did Winston live in Ireland with his parents (after his grandfather, the 7th Duke of Marlborough, was made Viceroy)? Two years old; he returned to England when he was five

 622. Was WSC ever a Freemason? Churchill was a Freemason from 1901-1912

 628. Who did Tories call the "Terrible Twins"? Churchill and David Lloyd George

 634. Why was Winston's engagement to Clementine in 1908 such a newsworthy event? Because he was a Cabinet Minister

 640. In 1932, when WSC returned from America, what gift was waiting for him on the dock? A Daimler

 646. "Anyone can rat, but it takes a certain amount of ingenuity to re-rat." What did Churchill mean by rat? Symbolized the desertion of one's party

 652. To Clementine's annoyance and Winston's amusement, who liked to hint he was Churchill's illegitimate son? Brendan Bracken

 658. In what churchyard (church and village) is Sir Winston buried? St. Martin's Churchyard, Bladon, Oxfordshire

 664. Fiel Pero Desdichado is the Churchill family motto. What does it mean? Faithful but Unfortunate

 670. "In a twinkling of an eye I found myself without an office, without a seat, without a party and without [what else?]." "...without an appendix"

 676. Where and when did Churchill first use paper money (and disliked it)? While visiting New York City in 1895

 682. What were Churchill's "belly-bandos"? Tape bands placed around the middle of Churchill's cigars

 688. How did Churchill get his first racehorse? Churchill's son-in-law, Christopher Soames bought Winston his first racehorse

 694. What was Winston's favorite brand of Cognac? Hine was Winston's favorite brandy

 700. What did Churchill call his occasional bouts of melancholy? "Black Dog"

 706. During WW2 Churchill's daughter Sarah was a Medmenham plotter. What was that? Sarah Churchill was at RAF Medmenham interpreting aerial photographs in 1943

 712. Which of his characteristics did Churchill think was a godsend for the cartoonists? The V-sign

 718. "[It] imparts a feeling of exhilaration the nerves are braced: the imagination is agreeable stirred; the wits become more nimble." What it is? "A single glass of Champagne"

 724. What was Winston's nickname at Harrow? "Copperknob" for his red hair

 730. About how many documents are in the Churchill Archives, including documents sent to or received by Churchill from childhood to his final years? About 1.5 million documents

 736. Why did Clementine object to Winston's purchasing of Chartwell? Because she wasn't consulted and didn't think it affordable 742. Doctor of Laws (Honoris Causa)

 742. What award was given to Clementine Churchill by Glasgow University in 1847?

 747. Where was Churchill taken after being run down by a private motorcar on 13 Dec. 1931? Lenox Hill Hospital

 750. On what occasion did Churchill write, "I consider myself a Democrat as far as American politics are concerned"? Churchill wrote to Burke Cochran on 16 July 1904 prior to the American elections

 751. Who (all) joined Churchill on a camel ride visiting the Pyramids on 15 Feb. 1921? T. E. Lawrence, Gertrude Bell and his wife Clementine, among others

 754. Who succeeded Churchill as First Lord of the Admiralty when he resigned in May 1915? Arthur James Balfour

 775. Who commented: "You appear to be leading a perfectly useless existence," and to whom was it addressed? Churchill commented in 1929 to his son Randolph that he was leading a perfectly useless existence.

 776. When did Churchill give his last speech in Parliament? 3 March 1955

 780. How did Lady St. Helier contribute to Churchill's future? Lady St. Helier, aka Lady Jeune, convinced Sir Evelyn Wood to get Churchill to the Omdurman campaign and in March 1908 held a dinner party where Winston devoted all his attention to his beautiful neighbour Miss Clementine Hozier.

 781. To whom did Churchill say, "We are all worms, but I do believe that I am a glow-worm."? Miss Violet Asquith

 796. In 1943 on a drive with President Roosevelt to Shangri-La, (now Camp David), Churchill recited a famous poem by an American poet. Can you name the poem and the author? "Barbara Frietchie" by John Greenleaf Whittier

 802. When was Churchill made an Honorary American Citizen? 1963

 808. Who owned Chartwell when Churchill purchased it? A. I. Campbell Colquhoun

 814. What was the paternal name of Churchill's grandfather? John Winston Spencer Churchill, 7th Duke of Marlborough.

 820. Churchill named a cat named after a famous British hero. What was its name? The cat at Churchill's Admiralty was named "Nelson."

 826. Who was the sculptor of the statue which stands at the British Embassy, Washington, D.C.? William M. McVey

 832. What was the name of Churchill's last bodyguard? Edmund Murray, who served from 1950 to 1965

 838. Who said of Churchill: "When Winston is right he is unique. When he is wrong-Oh My God!"? Lord Birkenhead

 844. When did Churchill attend his first American football game? In early 1930 when he visited at Columbia University and commented, "Actually it is somewhat like Rugby. But why do you have to have all those committee meetings?"

 850. When did Churchill comment that he found himself "without an office, without a seat, without a party and without an appendix"? After his defeat at Dundee in 1922

 856. What did Sir Emest Cassell provide Churchill for his new house in South Bolton Street in 1905? Furnished a library

 862. What is the significance of 15 September 1922 in Churchill's life? Mary Churchill (Lady Soames) was born, and on the same date, Churchill wrote to Knight, Frank and Rutley offering to buy Chartwell.

 868. How often was Churchill on the cover of Time Magazine? Eight times and as part of an eighth cover.

 874. What commercial brands of cigars were Churchill's favourites? Camacho and Romeo y Julieta cigars

 880. When did Churchill give his maiden speech in the Commons? 18 February 1901

 886. When were Winston Churchill and Clementine Hozier married? 12 September 1908

 892. What was Clementine Churchill's mother's maiden name? Blanche Ogilvie

 898. In 1955 Churchill received the first Williamsburg Award from the Trustees of Colonial Williamsburg. What is the purpose of the Award? "To serve as a continual reminder that there are today, as there were yesterday, vigorous, courageous and eloquent leaders, and is presented to a person who has made an outstanding contribution to the historic struggle of men to live free and self-respecting in a just society."

 904. Sotheby recently sold a car owned by Churchill from 1938 to 1950. What make was it? The car sold for £66,400, formerly owned by Churchill, was kept at Chartwell where it was engaged in staff errands. It was an Austin Ten saloon, license number EYH 409.

 910. Who quotes Churchill as "he thinks it is a brave thing to ride in triumph through Persepolis"? Isaiah Berlin quotes him in Mr. Churchill in 1940.

 916. When did Churchill buy Chartwell? September 1922

 922. Where is Sir Winston buried? Church of St. Martin's in Bladon, Oxfordshire

 928. When did Sir Winston receive the Williamsburg Award? Draper's Hall, London, 7 December 1955.

 934. How many of Churchill's speeches were broadcast from the House of Commons? No Churchill speeches were broadcast from the House of Commons.

 940. In what year was Churchill initiated into the Freemasons? 24 May 1901

 946. In 1905 Churchill was offered the Financial Secretaryship to the Treasury He was, however, able to convince the Prime Minister to appoint him to a different position. What was it? Under-Secretary for the Colonies in 1905

 952. In how many speeches did Churchill refer to "blood, toil, tears and sweat"? Six speeches: 13 May 1940, 8 Oct 1940, 7 May 1941, 2 Dec 1941, 27 Jan 1942 and 10 Nov 1942.

 958. What was Churchill's word of advice for budding artists? "audacity"

 964. What was the full name of Winston's brother Jack? John Strange Spencer Churchill

 970. Name Churchill's London residences with the blue historical plaque. 33 Eccleston Square; 2 Sussex Square; 11 Morpeth Mansions; and 28 Hyde Park Gate

 976. After Churchill's car accident in January 1932 in New York, Dr. Otto C. Pickhardt wrote a prescription for him. What did the doctor prescribe? "The use of alcoholic spirits at meal time...the minimum requirement to be 250 cc."

 982. What did Churchill call his mood swings which often enveloped him? "Black Dog"

 988. In 1943 Roosevelt and Churchill met in Casablanca. What was Churchill's code name during the first part of the trip? "Air Commodore Frankland"

 994. In one of his early writings, published by Pall Mall Magazine, Churchill described a day at Sandhurst and signed it with a pseudonym. What name did he use? "A Cornet of Horse," a rank once held by William Pitt, Earl of Chatham, and about whom Walpole wrote, "We must muzzle this terrible young Cornet of Horse."

 1000. In his acceptance speech of the leadership of the Conservative Party in 1940, Churchill claimed to have "always faithfully served two public causes." What were they? "The maintenance of the enduring greatness of Britain and her Empire and the historical continuity of our island."

 1006. In Thoughts and Adventures (Amid these Storms) Churchill expresses his opinion of people who get drunk. What was it? "I have been brought up and trained to have the utmost contempt for people who get drunk."

 1012. What was Sir Winston's favorite Champagne? Pol Roger

 1018. What was the name of the young lady whom Churchill pursued unsuccessfully during his first election campaign in 1899? Pamela Plowden, later Lady Lytton

 1024. On what occasion did Churchill say, "It was a nation and race dwelling round the globe that had the lion heart. I had the luck to be called upon to give the roar"? at his 80th birthday celebration in Westminster Hall on 30Nov54.

 1030. Stalin gave Churchill a Russian film which he praised in a letter to WSC on 19 December 1944. What was the name of the film? "Kutuzov"

Questions from FH 106

1036. When Churchill replaced Chamberlain as Prime Minister, what office did he want give the former Prime Minister? question moved to Statesman

 1042. Who was the first to tell Churchill of the German attack on Poland on 1 September 1939? Question moved to War

 1048. Where was Churchill's mother, Jennie Jerome, born? 426 Henry Street, Brooklyn, New York on 9 January 1854

 1054. What key position in Churchill's secretariart did Sir John Martin hold from 1941 to 1945? Churchill's Principal Private Secretary between 1941 and 1945

 1060. What artist both painted and wrote about young Winston in South Africa in 1899? Mortimer Menpes was the artist whose pictures of Churchill appeared on the cover of FHs 105 and 79

 1066. Where was the armoured train ambushed during the Boer War? Near Frere in Natal

 1072. What 1905 appointment gave WSC his first administrative experience? Undersecretary for the Colonies

 1078. About whom did Churchill say: "He made one terrible mistake. Obsessed in his youth by fear of the power of Spain, he failed to observe the rise of France"? Oliver Cromwell

 1084. Who presented Churchill with the marmalade cat WSC named "Jock"? Jock Colville

 1090. Where was Churchill imprisoned during the Boer War? States Model School in Pretoria

 1096. In which hotel did Churchill stay when he visited Los Angeles? Hotel Biltmore in Los Angeles in 1929

 1102. What was the "Black Move"? The plan for evacuating Churchill and all Government departments to the West of England in the event London being bombed.

 1108. What boat carried Sir Winston's coffin up the Thames at his funeral? Havengore

 1114. When Churchill checked into the Plaza Hotel in New York in 1931, and management rang his room to ask if he had any special needs, what did he reply? Pretending to be his valet, Churchill responded on the telephone: "Mr. Churchill is a man of simple tastes; he is quite easily satisfied with the best of everything."

 1120. What year was Churchill initiated into the Freemasons? 24 May 1901 at the age of 26

 1126. Which of WSC's secretaries was seated by his bed as he dictated, "Never in a field of human conflict was so much owed by so many to so few"? Mrs. Kathleen Hill

 1132. Who was the artist who created the Churchill statue situated at Westminster College, Fulton, Missouri? Franta Belsky

 1138. After Churchill escaped from the Boer prison he made a speaking tour of the United States, starting 8Dec00 and lasting through 2Feb01. How much was he paid? £1600

 1144. When Churchill entered Parliament he did not receive a salary. When did MPs begin being paid? 1911

 1150. What was Churchill's favorite hotel in Marrakesh, Morocco? Hotel La Mamounia

 Questions from FH 111

 1156. At Harrow, whom did Churchill push into the pool who later served as First Lord of the Admiralty? Leo Amery

 1162. In 1912 Churchill declared in a speech, "They are now the most serious obstacles to Anglo-American friendship." To whom did he refer? The Irishmen overseas

 1174. Who said, "When Winston was born lots of fairies swooped down on his cradle with gifts, imagination, eloquence, industry, ability; and then came a fairy who said, 'No one person has the right to so many gifts,' picked him up and gave him such a shake and twist that with all the gifts he was denied judgment and wisdom"? Prime Minister Stanley Baldwin

 1180. Why was Churchill unable to remain First Lord of the Admiralty after May 1915? Because the Tories would not join a Coalition

 1186. Where is Churchill's daughter Marigold buried? Kensal Green Cemetery, London

 1192. Name the Churchill family motto. "Fiel Pero Desdichado" (Faithful but Unfortunate)

 1198. When was Sir Jacob Epstein's bust of Churchill sculpted and cast? The Epstein bust of Churchill was cast in 1946.

 1204. In April 1922, an injured WSC was unable to play for the rest of the year. What happened to his ponies? Churchill sent one of his polo ponies to Sir Archibald Sinclair and kept two for morning rides in Rotten Row.

 Questions from 113

 1207. On 19 January 1935, Churchill was unpleasantly surprised by one of his son Randolph's rast decisions. What was it? Randolph ran as an Independent Conservative in Conservative stronghold Wavertree, and lost.

 1210. What event allowed Churchill to use the name Sir Winston? When Churchill became a Knight of the Garter in spring of 1953.

 1216. What financial award came with the Nobel Prize for Literature? Churchill received £12,093, tax free.

 1222. How old was Churchill when he became Prime Minister for the second (or officially the third) time? Churchill was 76 years old when he again became PM in 1951

Questions from 114

 1234. What name was originally given to intercepted German codes? (P)

 1240. What did Churchill call the Bletchley codebreakers? (P)

 1246. Anthony Bevir, who looked after patronage matters at No. 10 Downing
Street, recommended Churchill's name to King George VI's private secretary.
What did he recommend? (P)

 1252. When was Churchill first approached by the Conservative Party to stand as Tory candidate for Oldham? (P)

Churchilltrivia editor: Curt Zoller
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