Some have ventured to draw a line between Churchill’s painting pursuits with his legendary skill for writing. “How he picked up a paintbrush is analogous to how he picked up a pen to write a speech,” said Timothy Riley, director and chief curator of the National Churchill Museum in Missouri. “His paintings come from the same place. His brilliant mind, his vision, his power of observation informed him as a statesman, a writer, a reader, and as a painter.”

But his approach to painting was quite at odds with that of writing. While painting was a challenge, writing came to him naturally, and it was, for much of his life, how he earned a living. “With painting, Churchill was forever the keen student, whereas with words, he was always the master,” Carter said.

It may well be, though, that Churchill’s approach to painting was informed by his writing. “We know Winston Churchill as a great writer and speaker,” said Riley. “His speeches are some of the greatest of the 20th century, and what he did with words, moving people through speeches, he was trying to do with color and light and shadow—the things that painters use to convey a message, depict the world, and evoke emotion.”

Sandys believes that painting made Churchill a more effective leader, particularly thanks to the improved powers of observation and memory the hobby brought him. He pointed to the Battle of Britain in 1940, shortly after Churchill became prime minister, when he went to the front lines to observe the British defense firsthand. “Perhaps he thought that by going down there and looking at these things himself, he would see more and recall it more accurately,” Sandys offered, noting that it could’ve helped him to analyze the full picture of the battlefield, seeing the areas for improvement. “I think it’s a question that should be posed: Was painting a contributing factor to some of the decisions he made at that critical moment?” (Churchill himself drew parallels between the role of a general in battle and a painter.)