5 Times Winston Churchill’s Paintings Captured History 

Sir Winston Churchill is known the world over as an inspirational statesman, orator and leader who led Britain and the allied forces with Franklin Roosevelt to victory in World War II. What is less well known is that when he wasn’t making history, he was making art. Read on to learn more about Sir Winston Churchill’s paintings. 

Sir Winston Churchill in December 1941

Sir Winston Churchill in December 1941 (Wikimedia Commons).

The art of being a great statesman is a monumental challenge in itself, but to marry that with the mastery of another art is almost unheralded. He wasn’t just a master of the paintbrush though, as the irrepressible Churchill was also awarded the Nobel Prize in Literature in 1953 for his many published works, while also managing to find time to produce over 500 paintings.

Churchill picked up a paintbrush throughout his life to document his many experiences. He used them to document time he spent on the Western Front, when on active military service from 1915 to 1916; Ploegsteert Wood in Flanders, where he commanded the 6th Battalion, Royal Scots Fusiliers; perhaps most famously his time with The Tower of the Koutoubia Mosque during World War II.

Proving to revive his spirits and help combat his frequent bouts of depression, Churchill began with watercolor and soon applied himself to oils. In the end, he gave away around 100 of his paintings, although he was initially reluctant to do so, saying “they are too bad to sell and too dear to me to give”. His mind might have been changed had he known that The Tower of the Koutoubia Mosque would eventually sell for £8,285,000 in March 2021, demonstrating that his work had equal historical and financial significance. 

1. The Tower of the Koutoubia Mosque (1943)

Sir Winston Churchill: The Tower of the Koutoubia Mosque, c.1943.

Sir Winston Churchill: The Tower of the Koutoubia Mosque, c.1943. Sold for £8,285,000 via Christie’s (March 2021).

“We are here in a fairyland villa in Marrakech,” wrote Churchill in a telegram from 25 January 1943 to his wife. “Weather brilliant. Am going to paint a little this afternoon from roof of the same view of the pink gateway. My friend has gone.” His “friend” was Franklin Roosevelt and this was more than a painting documenting a holiday, but documenting history too.

Roosevelt had accompanied Churchill on a trip to Marrakech after they both attended the Casablanca Conference to determine the next stage of the war. Churchill worked on the picture from the balcony of the city’s Villa Taylor, where he and Roosevelt were staying. 

Adding to the painting’s importance, it was the only one Churchill produced during WWII and like so many of his “daubs” as he self-deprecatingly referred to them. He gave it to Roosevelt as a birthday present. It was inherited by Roosevelt’s son Elliot who sold it 1950, before it was exhibited at the National Churchill Museum at Fulton, Missouri, purchased by the actress Angelina Jolie and ultimately sold in 2021 for a record fee, surpassing the £1.765 million achieved in 2014 for The Goldfish Pool at Chartwell (1932).

2. Scene at Marrakech (1935)

Sir Winston Churchill – Scene at Marrakech, c. 1935.

Sir Winston Churchill: Scene at Marrakech, c. 1935. Sold for £1,882,500 via Christie’s (March 2021).

Churchill first visited Marrakech in 1935 at the behest of his friend and painting tutor, Sir John Lavery. He seemingly enjoyed painting the intense burnt orange of the desert sand and the bright blue skies of Morocco

Sir Winston Churchill: St Paul's Churchyard, 1927.

Sir Winston Churchill: St Paul’s Churchyard, 1927. Sold for £1,078,500 via Christie’s (March 2021).

Scene at Marrakech represents one of the most accomplished of Winston Churchill’s paintings and was produced during what are termed his wilderness years; after his time as Chancellor of the Exchequer and before he was appointed Prime Minister in 1940 to lead the war effort. 

And the war effort was in Churchill’s mind when he gifted the painting to the venerated Field Marshall Montgomery. Known as ‘Monty’ he was a favourite of Churchill’s who commanded the Allies in north Africa against General Erwin Rommel and was instrumental in delivering eventual victory in 1945. The painting remained with the Montgomery family before going under the hammer in 2021, along with Scene at Marrakech and a 1927 view of St Paul’s Churchyard, which were all purchased by the same bidder.

3. Troops Going to the Front (1917)

Depicting soldiers leaving their families on their way to the Front to fight in World War I, Troops Going to the Front’s deep and dark tones of brown and gray carry the heavy heart of soldiers waving farewell to their loved ones at Victoria Station in London, with the only bright color coming from a little girl in pink in the foreground. 

Inspired by a photograph taken by Francis James Mortimer, Churchill channelled his experience of life in the trenches for this 1927 painting, having served on the Western Front in 1915. 

It’s a rare example of Churchill’s painting offering some sort of social commentary, while also experimenting with darker tones and colors in favour of his usual bright blues and greens, and vivid oranges and yellows. “I cannot pretend to feel impartial about the colors,” he wrote in his 1965 book, Painting as a Pastime. “I rejoice with the brilliant ones and am genuinely sorry for the poor browns.” The painting was gifted to Rab Butler, Churchill’s private secretary during World War II before going to auction.

4. Beach at Walmer, 1938

Sir Winston Churchill: Beach at Walmer.

Sir Winston Churchill: Beach at Walmer, 1938. Sold for £313,250 via Christie’s (May 2011).

On the eve of war the following year, Churchill depicted the calm of a summer’s day at the beach in Walmer on England’s south coast, alongside the impending impact of a Napoleonic-era cannon. Folklore says that the Romans invaded Britain in 55 BC on the shores of Walmer, giving the site and painting an edge of historical significance that the inspirational leader would’ve doubtless been well aware of, as another international conflict loomed on the horizon.

The seascape painting offers a slight departure from the Claude Monet-inspired landscapes he regularly produced. And those with a keen eye will be able to spot a flash of red hair on the character in the centre of the painting, which is said to be Churchill. 

“Painting came to my rescue in a most trying time,” Churchill wrote in essays that would become a small book, Painting as a Pastime. Churchill would once again pick up the paintbrush to paint Villa on the Nivelle after the general election in 1945 that would ultimately bring his time as prime minister to an end (or for the time being anyway, as he served again between 1951 and 1955).

5. The Goldfish Pool at Chartwell (1932)

The pond at his Chartwell country home, where he lived from 1922 until his death in 1965, held a great deal of personal value. So much so that two of Winston Churchill’s paintings are dedicated to the subject. To this day a seat remains by the pond, from where he liked to feed his golden orfe fish at the house. Chartwell is now open to the public

Sir Winston Churchill: The Goldfish Pool at Chartwell, 1932.

Sir Winston Churchill: The Goldfish Pool at Chartwell, 1932. Sold for £1,762,500 via Sotheby’s (December 2014).

Influenced by the colors and brushstrokes of Monet, Churchill honed his skill with help from friends and pioneers of British art, Walter Richard Sickert and William Nicholson and he enjoyed setting up his easel whenever the urge to paint struck, which often was at his Chartwell home. “Just to paint is great fun. The colors are lovely to look at and delicious to squeeze out.”

A measure of how important to the pond at Chartwell was to him was confirmed when he revisited the pond in his final painting in 1962, three years before his death at the age of 90.