Sir Winston Leonard Spencer Churchill was the son of Lord Randolph Churchill and Lady Randolph who was an American woman and the daughter of a millionaire. Churchill had one brother and the boys were cared for by a nanny that Churchill fondly referred to as "Woomany".

In April 1888, Sir Winston Leonard Spencer Churchill entered the Harrow School. It was believed that Churchill wrote to his mother and asked for permission to return home or to at least come for a visit. He had very little contact with his father.

After leaving the Harrow School, Churchill went to Sandhurst where he attended the Royal Military College. In 1894, he graduated eighth in his class. Upon graduation, he was commissioned in the 4th Queen’s Own Hussars which was a calvary regiment in the British Army. After a brief time in the army, he became a Conservative Member of Parliament.

After becoming a Conservative Member of Parliament, Churchill held several high posts for the first part of the century. After the start of World War II, he held several titles including First Lord of the Admiralty, Prime Minister, and Prime Minister of Defense. He was a member of Parliament until 1964.

In 1953, Queen Elizabeth II bestowed on Churchill the honor of the insignia with the Order of the Garter. After his official retirement, he wrote a History of the English- Speaking Peoples which joined his other works of literary volumes. Sir Winston Leonard Spencer Churchill was also an accomplished painter and considered by many as very prolific with over five hundred paintings to his credit along with a few sculptures. Today, Tony Malone oversees his collection in London.