Sir Winston Churchill

Winston Churchill is best known as one of the 20th century’s most significant statesmen and orators, but he was also an accomplished painter whose artistic practice offered a counterbalance to the intensity of his political life.

Churchill began painting relatively late, in 1915, after his forced resignation from the Admiralty following the Gallipoli campaign. This newfound pursuit became a lifelong passion, providing him with solace, creative fulfilment and a means of expression during some of his most challenging periods.

Self-taught, Churchill approached painting with characteristic vigour and determination. He favoured landscapes and still lifes, capturing scenes from his home in Chartwell, his travels in Europe and the Mediterranean. His early work was influenced by the Impressionists, particularly their use of light and colour. Churchill worked predominantly in oils, which suited his bold, instinctive approach.

Key works by Churchill include The Goldfish Pool at Chartwell (1932), which reflects his affection for his Kent home, and Tower of the Koutoubia Mosque (1943), a vista across the city of Marrakech. His travels to the South of France, North Africa and other sunlit locales informed his palette, often characterised by luminous blues, greens and ochres.

Churchill’s art earned recognition during his lifetime. In 1921, he exhibited for the first time under the pseudonym Charles Morin to avoid undue attention. By 1947, his work had gained significant acclaim, and he became an honorary member of the Royal Academy. His book Painting as a Pastime (1948) offers a vivid reflection on his artistic philosophy, portraying painting as a therapeutic activity and a means of escaping the pressures of public life.

Although Churchill painted for personal enjoyment, his works are now regarded as an essential aspect of his legacy. They reveal an introspective and contemplative dimension to a figure often associated with action and rhetoric. Many of his paintings are held in private collections, with some displayed at Chartwell, now managed by the National Trust, offering a glimpse into the personal world of one of the 20th century’s most complex figures.

SIR WINSTON CHURCHILL, O.M., R.A. (1874-1965)

Tower of the Koutoubia Mosque

SIR WINSTON CHURCHILL, O.M., R.A. (1874-1965)

Scene at Marrakech

SIR WINSTON CHURCHILL, O.M., R.A. (1874-1965)

The Bridge at Aix-en-Provence

SIR WINSTON CHURCHILL, O.M., R.A. (1874-1965)

St Paul's Churchyard

Sir Winston Churchill, O.M., R.A. (1874-1965)

Villa on the Nivelle

Sir Winston Churchill, O.M., R.A. (1874-1965)

A View of Marrakech

Sir Winston Churchill, O.M., R.A. (1874-1965)

The Giza Pyramids at Cairo

SIR WINSTON CHURCHILL, O.M., R.A. (1874-1965)

View of the Mediterranean near San Raphael

SIR WINSTON SPENCER CHURCHILL (BRITISH, 1874-1965)

Interior, the Long Gallery at Sutton Place

SIR WINSTON CHURCHILL, O.M., R.A. (1874-1965)

Still Life, Silver at Chartwell

Sir Winston Churchill, O.M., R.A. (1874-1965)

The Cathedral, Hackwood Park

Sir Winston Churchill, O.M., R.A. (1874-1965)

The Beach at Walmer

Sir Winston Churchill, O.M., R.A. (1874-1965)

The Terrace at Mrs Alice Keppel's Villa d'Ombrellino near Florence

Sir Winston Churchill, O.M., R.A. (1874-1965)

The Ancient Olive Grove at La Dragonnière, Cap Martin

Sir Winston Churchill, O.M., R.A. (1874-1965)

Sunset over the Atlas Mountains

Sir Winston Churchill, O.M., R.A. (1874-1965)

The Seashore

Sir Winston Churchill, O.M., R.A. (1874-1965)

The Colleoni Memorial, Venice

SIR WINSTON CHURCHILL, O.M., R.A. (1874-1965)

The Canal at St-Georges-Motel

Sir Winston Churchill, O.M., R.A. (1874-1965)

The Ruins of Arras Cathedral (after Sargent)

Sir Winston Churchill, O.M., R.A. (1874-1965)

Valley of the Ourika, near Marrakech

Sir Winston Spencer Churchill, O.M., R.A. (1874-1965)

Woodland scene near Mimizan

Sir Winston Churchill, O.M., R.A. (1874-1965)

Garden Scene

Sir Winston Spencer Churchill, O.M., R.A. (1874-1965)

Café at St. Jean de Luz

Sir Winston Spencer Churchill, O.M., R.A. (1874-1965)

Inlet in the South of France

Sir Winston Churchill, O.M., R.A. (1874-1965)

Interior of a Studio, Lady Kitty Somerset at an easel

CHURCHILL, Winston Spencer (1874-1965). Portrait photograph depicting Churchill seated at the Cabinet Office table, an unusually large print, 244 x 195mm (348 x 280mm with mount), signed and inscribed on mount TO JOSEPH STALIN, 'From his Friend Winston S. Churchill, September 1944 To Marshal & Premier Stalin who at the head of the Russian Armies & of the Soviet Government broke the main strength of the German military machine & helped us all to open paths to Peace, Justice & Freedom' (very slight silvering to print, mount slightly soiled and creased at margins). Provenance : Sir John "Jock" Colville (1915-1987), assistant private secretary to Churchill: autograph note on label to verso, 'This photograph was inscribed by the P.M. for Stalin but it was then found that the silver frame for which it was destined obscured the inscription. He therefore rewrote it on another photograph and gave me this one. J.R.C.'; and by descent.

CHURCHILL, Winston S. (1874-1965)

[Collected Speeches. 1941-1948]

CHURCHILL, Winston S. For Free Trade. A Collection of Speeches Delivered at Manchester or in the House of Commons during the Fiscal Controversy preceding the late General Election . London: Arthur L. Humphreys, 1906.

CHURCHILL, Winston S. The Second World War . An archive of 13 galley proofs (comprising some 424 pages) plus 13 printed proofs (in octavo wrappers) of various versions of volumes I-VI, some with corrections and comments in Churchill’s hand; the majority of the extensive corrections in the hands of C. C. Wood and F. W. Deakin.

[CHURCHILL, Winston S.] Official War Office Photographs, 1940-1945. 3 volumes. Folio albums (12¼ x 15¾in.), stamped in gilt on upper cover, with Churchill's initials on upper right cover of each album. TOGETHER APPROXIMATELY 477 BLACK AND WHITE PHOTOGRAPHS, various sizes, each laid down on card. Albums bound with screws at left edge (one screw missing from second album), slight rubbing to covers, images fine.

CHURCHILL, Winston S. Archive of over 60 typed letters signed and memoranda signed ("Winston S. Churchill", "W.S. Churchill," "W.S.C."), along with 10 printed telegrams, to C. C. Wood, 1933-1956. Also including letters, memoranda and galleys passed between Churchills' ghost writers and editors (William Deakin, Denis Kelly and Wood), several with autograph endorsements and annotations in Churchill's hand. Together approximately 170 pages, various sizes, a few letters signed by Churchill's secretary Violet Pearman, two letters with Churchill signatures clipped away .

CHURCHILL, Winston S. Archive of 29 typed letters signed ("Winston S. Churchill" or "W.S.C.") to Sir Emsley Carr and Major D. Percy Davis, et al., the editors of The News of the World , 1934-1951. Together 39pp., 4to, on personal, Admiralty, and 10 Downing St. stationery . [ALSO WITH:] 10 additional letters from Clementine Churchill, Anthony Eden ("Avon"), Alec Douglas-Home and Edward Heath, 1965-1979.

CHURCHILL, Winston S. Autograph letter signed to Eliot Crawshay-Williams, 10 Downing St., 28 June 1940, one page, 8vo ; with a letter to Churchill by Crawshay Williams, 27 June 1940. Provenance : Sotheby's, 14 December 1992, lot 37.

CHURCHILL, Winston S. Autograph letter signed ("W.") with an autograph postscript signed ("W.S.C."), to Jack Churchill, 19 June 1915. 9 pages, 8vo, Duchy of Lancaster stationery; with original autograph envelope signed ("Winston S. Churchill") . Marked "private & secret."

CHURCHILL, Winston S. (1874-1965). Churchill's full-cut crocodile-skin cigar case, c.1934, by Cartier Ltd, London, the initials 'W S C' set in brass on the fastening, length 170mm x width 90mm, a single cigar (unmarked) remaining in the four-cigar chamber. Provenance : manufactured especially for Churchill in c.1934 (information from Cartier archives); given by Clementine Churchill to Churchill's former bodyguard Inspector Cyril Davies after Churchill's death (typed letter signed, 22 June 1965; compliments slip 'Sent with Lady Spencer-Churchill's compliments and good wishes'); acquired by the present owner from Davies's estate; [ with ] three telegrams from Churchill to Inspector Davies, acknowledging birthday wishes in 1959, 1963 and 1964.

CHURCHILL, Winston S. Autograph letter signed to 'My dear General' (Sir Ian Hamilton), 'In the train Sudan Military R[ailway]', 16 September 1898, including a postscript signed with initials, mostly in blue ink, 17½ pages, 8vo (one passage heavily cancelled by recipient).

CHURCHILL, Winston S. The Interior of Sir John Lavery's Studio with two Ladies , oil on canvas board, 18 x 12in. (457 x 305mm), painted c.1922. Provenance : Sarah, Lady Audley; The Studio, Chartwell; Christie's, 20 June 1996, lot 73.

CHURCHILL, Winston S. My Early Life. A Roving Commission . London: Thornton Butterworth Limited, 1930.

CHURCHILL, Winston S. (1874-1965)

The Second World War . Boston: Houghton Mifflin, 1948-1954.

CHURCHILL, Winston S. (1874-1965)

A History of the English-Speaking Peoples . London: 1956-1958.

[CHURCHILL, Winston S.] ASQUITH, Lady Cynthia (1887-1960). Autograph manuscript journals, 1914-1919, a sequence of ten volumes kept during and after the First World War, London, Stanway, Brighton and other places, 15 April 1915 - 9 November 1919, together with an unpublished "Account of my motor expedition in France", 25 October 1914, including a large number of unpublished passages, approximately 2,300 pages, 4to, annotations, underlinings, cancellations and page numberings in various hands in pencil, crayon and ballpoint ink, some passages cancelled for publication; bound in green, blue, and red morocco, or black moleskin (one), 235 x 190mm - 270 x 220 mm, paper labels (clasps forced open or removed causing damage to covers; covers of volume II detached; scuffed, worn and splitting in spines); with a commonplace book running up to 1946. Provenance: her son Simon Asquith (his signature to 4 volumes); Sotheby's, 22 July 1988, lot 302.

CHURCHILL, Winston S. Autograph letter signed ("your loving brother, W.") to Maj. John Churchill, London, 12 June 1915. 3½ pages, 8vo, Duchy of Lancaster stationery, with original autograph envelope signed ("Winston S. Churchill"), with wax seal .

CHURCHILL, Winston S. Draft typescript signed ("Winston S. Churchill"), undated and untitled article on tensions between Russia, Japan and China [ca. 1931]. 7 pages, 4to , WITH CHURCHILL'S EXTENSIVE AUTOGRAPH REVISIONS in red ink, signed in red ink (some smudging of signature), punch hole top left corner, pencil note in another hand at top ("For Mr. Ranck") .

CHURCHILL, Winston S. and TRUMAN, Harry S. Oversized black and white photograph signed ("Winston S. Churchill"), as Prime Minister, and ("Harry S. Truman"), as President, aboard the U.S.S. Williamsburg, 5 January 1952. 14 x 18in., matted and framed, signed by each man on the matt, below their image. [ Loosely inserted in frame :] CHURCHILL. Autograph note signed ("Winston S. Churchill") to Harry S. Truman, [Washington], January 1952 1 page, oblong . Provenance : Pamela Harriman, her sale Sotheby's New York, 19 May 1997, lot 125.

CHURCHILL, Winston S. A COMPLETE SIGNED AND INSCRIBED SET OF THE FIRST EDITION OF THE WARTIME SPEECHES. Into Battle . London: Cassell and Co. 1941. 8 o . Half-title. Blue cloth (lightly rubbed), gilt spine. FIRST EDITION, sixth impression (mistakenly termed "edition"). INSCRIBED AND SIGNED on flyleaf "To Alfred J. Salisbury from Winston S. Churchill December 1941." Woods A66(a). -- The Unrelenting Struggle . London: Cassell and Co. 1942. 8 o . Frontispiece and four additional half-tone plates. Half-title. Blue cloth, gilt spine. FIRST EDITION, SIGNED AND INSCRIBED on flyleaf "To Albert J. Salisbury from Winston S. Churchill 1942." Woods A89. -- The End of the Beginning . London: Cassell and Co., 1943. 8 o . Half-title. Frontispiece and four other half-tone plates. Blue cloth, gilt spine. FIRST EDITION, SIGNED AND INSCRIBED on flyleaf "To Mrs. Salisbury from Winston S. Churchill Christmas 1944." Woods A94. -- Onwards to Victory . London: Cassell and Co., 1944. 8 o . Half-title. Frontispiece and four other half-tone plates. Blue cloth, gilt spine (corners lightly rubbed). FIRST EDITION, INSCRIBED AND SIGNED on flyleaf "To Mrs. Salisbury from Winston S. Churchill Christmas 1944." Woods A101. -- The Dawn of Liberation . London: Cassell and Co., 1945. 8 o . Half-title. Frontispiece and four additional half-tone plates. Blue cloth, gilt spine (spine rubbed). FIRST EDITION, INSCRIBED AND SIGNED on flyleaf "To Mrs. Salisbury from Winston S. Churchill, for yr library." Woods A107. -- Victory . London: Cassell and Co., 1946. 8 o . Half-title. Frontispiece and four additional half-tone plates. Blue cloth, gilt spine (slight rubbing to tip of spine; offset on front flyleaf). FIRST EDITION, INSCRIBED AND SIGNED on flyleaf "To Mrs Elsie Salisbury from Winston S. Churchill 1946." Woods A112. Together 6 items . (6)

CHURCHILL, Winston S. Thoughts and Adventures . London: Thornton Butterworth Limited, 1932.

CHURCHILL, Winston S. Autograph letter signed ('Winston S. Churchill') to Pamela [Plowden, later Countess of Lytton], [States Model School prison], Pretoria, 18 November [1899], one page, 4to ; envelope with stamp of Commandant General and other markings. Provenance : by descent from Pamela, Countess of Lytton; Christie's, 2 December 2003, lot 49.

CHURCHILL, Winston S. Draft typescript signed ("Winston S. Churchill"), n.d. [ca. March 1931]. 8 pages, 4to, punch holes at top left (linked by green ribbon); signature smudged; a few emendations in Churchill's hand, others by a copy editor .

CHURCHILL, Winston S. Draft typescript signed ("Winston S. Churchill"), "The Economic Collapse of Europe," n.d. [ca. 1931]. 13 pages, 4to , EXTENSIVELY CORRECTED IN CHURCHILL'S HAND, slight staining along a few margins, punch hole top left corner .

CHURCHILL, Winston S.; ROOSEVELT, Franklin D.; STALIN, Josef. Autographed White House card SIGNED BY EACH OF THE BIG THREE: ("J. Stalin," "Franklin D. Roosevelt," and "Winston S. Churchill"), signed as General Secretary, President, and Prime Minister, respectively, n.p., n.d. (likely Teheran Conference, 28 November - 1 December 1943). 1 page, oblong (2 x 4in.) card embossed with the Great Seal of the United States. Laid down in an 8 o , brown leather autograph album that ALSO CONTAINS THE SIGNATURES OF 62 FAMOUS POLITICAL, MILITARY AND ENTERTAINMENT FIGURES.