“Mad Jack” Churchill

In the British military during the Second World War, John Malcolm Thorpe Fleming Churchill served as an officer. He was also referred to as "Mad Jack" Churchill and was renowned for his distinct fighting technique. Typically, he would start the combat by playing the bagpipes before drawing his unit into a charge with his broadsword or longbow. He was also a skillful leader who frequently succeeded in his raids against Nazi outposts during the war, which may sound absurd for the period.

Churchill was unquestionably a successful officer, garnering several honors for his activities throughout the war, despite being known as "Mad Jack" due to his risk-taking fighting style. Churchill was undoubtedly one of the best swordsmen alive during the time he lived in, however he may not have had a chance against any other swordsman on this list in a contest of pure skill.