History’s Finest: The Legacy Of Sir Winston Churchill

“We shall fight on the beaches, we shall fight on the landing grounds, we shall fight in the fields and in the streets, we shall fight in the hills; we shall never surrender.”

The above quote is synonymous with the fighting spirit of the Allied forces during the Second World War. These great words come from the mouth a of a great man, fighting for the greatest cause: freedom against ultimate tyranny. The year is 1940 and the forces of Adolf Hitler, a man history knows to epitomise evil, is approaching the British isles from the newly-conquered French coast. Neville Chamberlain has resigned from his post as Prime Minister in a bout of fear and political failure. The British people, and all the peoples of the free world for that matter, turn its gaze and hopes to the leadership prowess of one underdog (AKA ‘The Bulldog’): Winston Leonard Spencer-Churchill. The following is the life, work, and legacy of arguably the 20th centuries’ finest man.


“Never give in, never give in, never, never, never, never—in nothing, great or small, large or petty – never give in except to convictions of honour and good sense.”

Young Winston was born on the 30th of November, 1874 to a British politician father and an aristocratic American mother. Though both highly sociable people, Winston’s parents were distant from both each other and their children. Their son was instead raised by Elizabeth Everest, the family nanny. Winston held this woman to be his truest and greatest friend throughout his entire childhood. Unlike other greats of the past, Winston’s greatness was not necessarily set in stone. The young gentleman struggled in school and fought with various speech impediments. Furthermore, an 18-year-old Winston nearly died after falling off a bridge while playing tag with his brother and cousin. Winston’s rise through the political and social ranks was somewhat of a miracle.

As is seemingly common with the History’s Finest series, Winston was an author, writing two books before his 25th birthday. These were mostly concerned with the military. This skill granted him a highly-paid post as a correspondent to the Boer War – a post that would win him fame in an unusual circumstance. After being captured by the enemy, Winston refused captivity and escaped into the African wilderness, where he was later taken in by a British farmer and hidden in a mine shaft until rescue was afforded. Upon return home, Winston utilised his newfound fame and notoriety as a British escape artist to secure a seat in the House of Commons as a conservative in 1900. This would be the beginning of a turbulent and illustrious 55-year political career. Eight years later, Winston married Clementine Hozier. The couple would make for a strong political team, with many reports stating that Winston ‘told Clemmie everything’. The Churchill’s bore five children, with four surviving into adulthood.

A series of missteps and career changes saw Winston in and out of politics over the following decades. But the Bulldog always wrote and was a popular public figure. So much so that in the early moments of the Second World War, on Britain’s brink of defeat at the hands of the Nazis, Winston’s country agreed that strong new leadership was necessary against the incurring evil. A veteran orator and public persona, Winston willingly took over as prime minister in the darkest hour.

Young Winston at The Royal Military Academy, Sandhurst.


“Statesmen are not called upon only to settle easy questions. These often settle themselves. It is where the balance quivers and the proportions are veiled in mist, that the opportunity for world-saving decisions presents itself.”

Prime Minister Winston Churchill would remain in office for the remainder of the Second World War and lead his nation through its most trying time. Unlike Chamberlain before him (as well as many fellow politicians), Winston understood that fighting – not surrender – was the only option. Therefore, victory was the only option. Through the aerial Battle of Britain and beyond, Winston defended his island nation with blind confidence necessary to stop Hitler’s war machine. He actively sought the friendship of American president Franklin D. Roosevelt during a trip to the White House mere weeks after the attack on Pearl Harbour. However, it was Winston’s friendship with the Russians that was most curious. The prime minister had been extremely vocal in his dislike of communist doctrine, and even more so in his dislike of Stalin. But as the Nazis pursued an Eastern front by invading Russia, Churchill and Stalin postponed their differences to unite against a common enemy.

The Allies lead by the Americans, Russians, and British were, of course, the victors of the Second World War in 1945. Winston would lose re-election as prime minister in the same year but serve again briefly in 1951, before stepping down at age 80. The orator continued to travel the world and spread concern for the growing danger of communism – the new evil spreading throughout Europe. The series aptly titled The Second World War also won Winston a Nobel Prize for literature. And finally, in 1965 at age 90, Britain’s finest passed on from this life on to the next.

Unmatched in oratory prowess.


“If you’re going through hell, keep going.”

The image of Winston Churchill is one of a gruff yet humorous old man, a cigar in one hand and a scotch in the other. This is a sharp contrast to the regal Marcus Aurelius or the studious J.R.R. Tolkien. Unlike these men, Winston’s greatness was not written in the stars. But a boy with a speech impediment became the voice of a generation against a ruthless tyrant. A boy without loving parents became a committed father and loyal husband. And finally, a boy who barely passed his entrance exams for military school was the prime mover against one of the greatest evils the world has ever seen. Truly a commendable legacy.

RELATED: ‘History’s Finest: The Legacy Of William Wallace’

But Winston struggled with more than just outside circumstance. As far as he could recall, the great prime minister battled with depression; what he called the ‘black dog’. This, Winston knew, was his greatest battle – the battle for one’s spirit. For any of you out there, across time and across the world hearing or re-hearing this story of Winston Churchill, know that his example is one of courage and determination against evil. But most of all, Winston’s legacy is one of victory over one’s own demons, over one’s own self. And whether you are fighting Adolf Hitler or just fighting to make it through the day, perhaps the victory over one’s self is the most honourable victory of all.

The most capable man in the darkest hour.


Jay is a writer and content producer for The Versatile Gent.

Leave a Reply

Your email address will not be published. Required fields are marked *