From cigars to canvases, a chance visit to the Wallace Collection reveals Winston Churchill the painter — and an extraordinary wartime gift to Roosevelt.
By David Mason.
A portrait of Winston Churchill at the Wallace Collection (2026)
Credit: Paul Quezada-Nieman
Winston Churchill must be turning in his grave.
It is one of those phrases deployed so frequently that the old boy must by now be rotating at considerable speed. But the latest proposals from Britain's health establishment have inevitably brought it out again.
Having already rendered the cigarette packet virtually unrecognisable beneath regulation brown and increasingly gruesome photographs, health ministers are now considering extending similar rules to premium cigars. The centuries-old artwork decorating cigar boxes and the elaborate bands encircling handmade cigars could disappear beneath standardised packaging and graphic health warnings.
The elaborate lithographed artwork of a traditional Romeo y Julieta cigar box — Winston Churchill’s favourite brand — which later named its celebrated ‘Churchill’ size in his honour. A centuries-old tradition of cigar-box art that could disappear from British shelves under proposed standardised packaging rules.
Credit: Jansos
For a country that once produced perhaps the most famous cigar smoker in history, the irony has proved irresistible.
I mentioned the story to my eldest son Elliot, who suggested that we spend the afternoon at the Wallace Collection in Marylebone, where an exhibition was exploring another, rather less familiar side of Winston Churchill...
His paintings.
PAINTING AS A PASTIME
The familiar Churchill can almost be reduced to a silhouette: Homburg hat, bow tie, cigar and two fingers raised in a V.
The man behind that silhouette was considerably more complicated.
Churchill did not begin painting until he was forty. In 1915, following the catastrophe of the Dardanelles campaign and his departure from the Admiralty, he found himself politically isolated and deeply despondent. It was during this period that he first picked up a paintbrush.
Winston Churchill, painted in 1915 by Sir John Lavery, who — together with his wife, Hazel, Lady Lavery — encouraged and mentored Churchill as he discovered painting during one of the most difficult periods of his political life.
Credit: piemags
What began almost accidentally became one of the great consolations of his life.
Churchill painted landscapes, interiors, still lifes and portraits, working principally in oils. He painted at Chartwell and wherever his travels took him: France, Italy, Egypt and particularly Morocco, whose light and colour fascinated him.
Over the course of his life he produced around 500 paintings.
Five hundred.
That would constitute a respectable life's output for somebody whose principal occupation was painting.
Winston Churchill painting the Chateau St.Georges-Motel in the Eure district of Normandy, France (1937).
Credit: Fremantle
Churchill, of course, had one or two other things going on.
He served twice as Prime Minister, was Chancellor of the Exchequer, Home Secretary, First Lord of the Admiralty and held a succession of other Cabinet offices. He was a soldier, war correspondent and Member of Parliament for more than half a century.
And then there were the books.
Churchill produced 43 book-length works, comprising 72 individual volumes, ranging across history, biography, politics and memoir. His literary achievements culminated in the award of the Nobel Prize in Literature in 1953, cited for his mastery of historical and biographical description as well as his oratory in defence of human values.
Winston Churchill at work in his study at Chartwell (February 1939).
Credit: Fremantle
Quite where he found the time is one of the more intriguing questions of twentieth-century history.
Part of the answer lay in an extraordinary working routine. Churchill dictated vast quantities of his writing and correspondence to secretaries, frequently while walking around his room or even from his bed. His habit of taking an afternoon nap effectively divided his working day into two, allowing him to continue long into the night.
Somewhere among the wars, elections, Cabinet meetings, speeches, books, memoranda, lunches, dinners, cigars and glasses of Pol Roger, Churchill found time to set up an easel.
And paint.
THE PAINTER AT WAR
One painting at the Wallace Collection caught our attention in particular.
Tower of the Koutoubia Mosque.
The picture depicts Marrakesh, the minaret of the great Koutoubia Mosque rising above the city, with the snow-covered Atlas Mountains beyond.
The 12th-century Koutoubia Mosque in Marrakesh, with the Atlas Mountains beyond.
Credit: Martin Moxter
Its significance extends considerably beyond its merits as a painting.
In January 1943, Churchill and Franklin D. Roosevelt met in Morocco for the Casablanca Conference. For ten days, the British and American leaders and their military staffs debated Allied strategy and the next phase of the war against the Axis powers.
US President Franklin Roosevelt and British Prime Minister Winston Churchill at the Casablance Conference, Morocco (January 1943).
Credit: World History Archive
It was an episode we encountered recently in the pages of The Transatlantic Journal.
In our article Dinner Key: When Miami was the Gateway to the World, we followed Roosevelt's remarkable wartime journey from Dinner Key in Miami aboard Pan American's Boeing 314 flying boat, the Dixie Clipper, across the Atlantic to Africa.
The President travelled under the codename Mr Jones.
At the conclusion of the Casablanca Conference, Churchill had another idea.
Roosevelt, he insisted, could not possibly travel all the way to Morocco without seeing the sunset over the Atlas Mountains.
The Koutoubia Mosque as sunset.
Credit: Kat Kallou
And so two of the most powerful men in the world temporarily abandoned the business of winning a world war and travelled some 150 miles south from Casablanca to Marrakesh, simply to watch the sun set over the Atlas Mountains.
SUNSET OVER THE ATLAS
The two leaders stayed at Villa Taylor, from whose tower there was a magnificent view across Marrakesh towards the mountains.
Roosevelt had been paralysed from the waist down since contracting what was then diagnosed as polio in 1921, and reaching the rooftop presented a considerable challenge. Unable to climb the stairs, the President was carried to the top of the villa so that he could take in the view Churchill had been so determined to show him.
There, as the winter sun descended behind the snow-capped Atlas Mountains, Roosevelt and Churchill sat together and watched the changing light over Marrakesh.
Churchill and Roosevelt watch the sunset on the snows of the Atlas Mountains from the tower of Villa Taylor (24 January 1943).
Credit: Everett Collection
It is an extraordinary image.
Europe remained occupied. The Battle of Stalingrad was reaching its bloody conclusion. The war in the Pacific continued. Millions of men were under arms.
Yet for a few minutes, the British Prime Minister and the President of the United States simply watched the sunset.
Roosevelt departed the following day.
Churchill stayed behind.
And took out his paints.
He painted the view dominated by the twelfth-century Koutoubia Mosque, illuminated by the Moroccan sun with the Atlas Mountains behind it.
Tower of the Koutoubia Mosque by Winston Churchill (1943)
Credit: Christie's
It was the only painting Churchill completed during the Second World War.
That fact alone makes Tower of the Koutoubia Mosque remarkable.
What Churchill did with it makes it considerably more so.
He gave it to Roosevelt.
THE ART OF DIPLOMACY
The painting was sent to the President as a birthday present.
There was something distinctly Churchillian about the gesture.
This wasn't a ceremonial object selected by the Foreign Office or an official gift exchanged between governments. Churchill had personally painted the landscape the two men had experienced together immediately after one of the most important Allied conferences of the war.
It was friendship, memory and diplomacy captured on canvas.
The art of the Special Relationship: Winston Churchill and Franklin D. Roosevelt share a bench on Old Bond Street in "Allies", Lawrence Holofcener’s bronze tribute to the wartime friendship between Britain and America. Unveiled in 1995 to commemorate 50 years of peace, it captures in bronze the relationship Churchill had captured on canvas more than half a century earlier.
Credit: Roberto Herrett / LOOP IMAGES
Churchill understood instinctively something that governments sometimes forget: personal relationships matter.
The relationship between Churchill and Roosevelt was certainly strategic, occasionally difficult and always conditioned by the national interests of Britain and the United States. But Churchill worked assiduously to make it personal.
There were dinners, late-night conversations, jokes, journeys — and now a painting.
Soft diplomacy, executed with a paintbrush.
FROM ROOSEVELT TO HOLLYWOOD
Roosevelt treasured Churchill's gift until his death on 12 April 1945, only weeks before victory in Europe, after which it was inherited by his son Elliott.
Winston Churchill with his daughter Sarah, leaving the memorial service at St Paul's Cathedral for the American President Franklin D Roosevelt (17 April 1945).
Credit: Dave Bagnall Collection
In 1950, Elliott Roosevelt sold the painting to Nebraska businessman George W. Woodward, before it was acquired in 1964 by New York financier, collector and film producer Norman G. Hickman.
There was a pleasing connection: Hickman had worked on The Finest Hours, the 1964 documentary about Churchill's life. During his ownership, the painting was exhibited at the National Churchill Museum in Fulton, Missouri — the city where Churchill had delivered his famous “Iron Curtain” speech in 1946.
Winston Churchill painting at the Surf Club, Miami Beach on 2 February 1946. The following month he traveled to Westminster College in Fulton, Missouri, where President Truman introduced Churchill before his historic Iron Curtain Speech on 5 March 1946.
Credit: Everett Collection
The painting remained with Hickman’s family for nearly half a century, until it was placed with New Orleans dealer M.S. Rau in 2011.
And then it acquired an unexpected Hollywood chapter.
Brad Pitt reportedly bought Tower of the Koutoubia Mosque from the dealer that year as a gift for his then-partner Angelina Jolie. The couple married in 2014 and separated two years later.
In 2021, amid their lengthy and acrimonious divorce, the painting resurfaced at Christie’s in London, offered for sale by the Jolie Family Collection.
Churchill’s Tower of the Koutoubia Mosque is prepared for Christie’s Modern British Art auction in London on 1 March 2021.
Credit: Mark Thomas
Its estimate was £1.5 million to £2.5 million.
It sold for £8.285 million.
A world auction record for Winston Churchill.
Not bad for a pastime.
THE ART OF CHURCHILL
Leaving the Wallace Collection, it was difficult not to reconsider the familiar caricature.
The cigar remains there, of course.
So do the Homburg, the bow tie, the siren suit, the V-sign, the speeches and all the other ingredients from which the popular image of Churchill has been assembled.
Winston Churchill, with signature cigar and siren suit, painting at Chartwell in 1946, reunited after the war with one of his greatest pleasures — brushes, oils, a canvas and his beloved Kent home.
Credit: Fremantle
But behind them was a man of almost bewildering productivity.
A politician who helped shape much of the first half of the twentieth century.
A writer who filled 72 volumes and won the Nobel Prize.
And an amateur painter who produced some 500 pictures — one of which captured a quiet Moroccan skyline shared with an American President in the middle of a world war.
There is a pleasing circularity to encountering that painting now.
Only a few weeks ago, researching Gateway to the World led us from an abandoned Pan American terminal on the shores of Biscayne Bay to Franklin Roosevelt's secret flight aboard the Dixie Clipper, to Casablanca and eventually to that sunset in Marrakesh.
Then, quite unexpectedly, an afternoon in Marylebone brought us face to face with the object that resulted from it.
And all because Britain's latest argument about cigars had caused Winston Churchill to turn in his grave once again.
A family portrait: Winston Churchill painted by his younger brother, Major John Strange Spencer-Churchill, shortly after victory in Europe (June 1945).
Credit: The History Emporium
Eighty-three years after Churchill gave Roosevelt a painting of a Moroccan sunset, somebody paid £8.2 million for it.
Which suggests that, whatever eventually happens to the artwork on his cigar boxes, Winston Churchill's other artwork is unlikely to disappear quite so easily.
Footnote:
Winston Churchill: The Painter is at the Wallace Collection, London, from 23 May to 29 November 2026.