What do Angelina Jolie, Winston Churchill, and Franklin D. Roosevelt have in common? To the surprise of many, the answer is a painting.

The actor, director and philanthropist is now selling the only painting created by British Prime Minister Winston Churchill during the second world war, and the work is expected to fetch up to £2.5 million at Christie’s in a few weeks.

Adding to its powerful provenance and celebrity status, “Tower of the Koutoubia Mosque” (1943) was the only work that the then prime minister painted during the second world war, and was gifted by him to President Franklin D. Roosevelt. They had visited Marrakesh together after the 10-day Casablanca Conference in 1943, which is what inspired Churchill to create the work.

“It is the only work that Churchill painted during the war, perhaps encouraged by the recent progress made by the Allies in what he considered to be one of the most beautiful countries he had encountered,” Nick Orchard, head of modern British art at auction house Christie’s, said in a statement.

The painting, which depicts the 12th-century mosque against the backdrop of the Atlas Mountains, has a rather complicated provenance, which warrants its current estimate. It was passed on to Roosevelt’s son when he died and it was then sold in 1950 to a Nebraska collector. The collector then sold it to the author, producer, financier and collector Norman G. Hickman, who had served as associate producer of the Churchill-themed film The Finest Hours in 1964. While it was in his possession, it was exhibited at the New York Daily News building and later at the Churchill Memorial in Fulton, Missouri during 1970. Upon Hickman’s death, it was passed to his second wife and then to her daughter, where it was stored in a closet for fifteen years. It was eventually acquired by the New Orleans dealer MS Rau and was put up for sale with a guide price of just under $3 million, which was when the Jolie Family Collection bought the work in 2011.

Churchill famously took up painting in 1915, when he was 40. In his writings, the wartime prime minister references the influence of the painter Henri Matisse, who had also spent time in Morocco earlier in the 20th century.

Churchill’s works can now command considerable sale prices, particularly if they have impeccable provenance (as in the case of Jolie’s Marrakesh, as well as Truman’s). In 2007, a painting of a view from Churchill’s home, “Chartwell Landscape with Sheep”, set a record for one of his works when it sold for £1m.