Did Adolf Hitler and Winston Churchill ever meet in person? The answer is no. They never had a face-to-face encounter, a handshake, dinner, or anything else at any time.
The closest Churchill came to meeting Hitler was when both were invited to a banquet in 1932. Hitler cancelled at the last minute and after that the two never crossed paths again.
Before World War One there was a strange connection between Churchill and the Kaiser. In 1909 Churchill travelled to Germany where he watched German military drills. He also sat next to the Kaiser at a public event. There is even a photo of them together showing a relaxed moment between them.
Churchill’s distrust of the Kaiser grew because he felt the Kaiser sometimes tried to show off his power.
In the end both men were on opposite sides in both World War One and World War Two.