Inspirational Wartime Leaders are Often Unwittingly Made by the Very Enemies that Oppose Them.

Zelenskyy, like Churchill before him, has responded to overt aggression from a warlike dictator, to become the very enemy the dictator did not want to face.

Peter Winn-Brown
6 min readApr 1, 2022
Volodymyr Zelenskyy & Winston Churchill: Inspirational wartime leaders both.

With comments that presaged many 20th and 21st Century conflicts, including Vietnam, Rhodesia, Chechnya, Iraq, Russia-Afghanistan, NATO-Taliban, as well as perhaps the current Russia-Ukraine war, the great British wartime leader Winston Spencer Churchill was clear-eyed about the immense difficulties of putting down a motivated “liberation” insurgency replete with local geographical and strategic knowledge, and high levels of civilian support.

Showing remarkable awareness at a very young age — he was only 25 (see image above) when he secured the Oldham seat at the so-called ‘Khaki’ election in 1900 upon his return from the Boer War and made the observations above— of the difficulties in facing down a highly motivated and localised insurgency, Churchill wrote that the assumptions made by the British forces in the latter stages of the Boer War were errors that, “were destined to cost us (the British) dear (1).”

This came after the British had effectively quelled all major resistance across the Boer Republics and wrongly assumed they would mop up the last vestiges of localised resistance with relative ease.

He continued, “There were still many thousands of wild, fierce, dauntless men under leaders like Botha, Smuts, De la Rey and Hertzog who now fought on in their vast country, not for victory, but for honour. The flames of partisan warfare broke out again and again far behind the armies in regions completely pacified (1).”

His words seem to frame the current Ukraine-Russia war almost perfectly. Putin has badly misinterpreted the Ukraine question, and did not anticipate the flames of partisan Ukrainian resistance and their burning desire for their own independence and freedom.

He wrongly thought that the Ukrainian armed forces would not stand up against him, and that the people of Ukraine would welcome his Russian army with cheers, flowers and adulation as liberators.

He wrongly thought the West, decadent and divided, would do little to stand in the way of his imperialist, revisionist agenda.

He wrongly thought that the ex-comedian with poor ratings and little or no experience, would cave and flee, leaving an open field with a pliable, compliant people who would willingly raise the Russian flag in surrender.

In all of these things, Putin was wrong. He was badly wrong.

He badly miscalculated and it has, just like the British in Southern Africa, cost them dear.

“Some are born great, some achieve greatness, and some have greatness thrust upon them.”

Shakespeare’s Twelfth Night: Act 2, Scene 5.

Churchill, of course, went on to become the quintessential British wartime leader, famous for his stirring speeches, his cigar and his bulldog persona.

Up until his political resurrection in 1940 Churchill had been a mercurial, inconsistent and often overly headstrong politician who had had his successes, but also more than his fair share of failures. Emerging from what became known as his ‘wilderness years’ Churchill found himself in his element as a wartime leader.

He was literally, the right man for the job.

As Margaret MacMillan wrote just a few days ago, it is enough “to recognize that who holds office at a particular moment in a particular place can make a critical difference. In a great crisis, the eve of a war, for example, it matters who has the final authority to say stop or go. It also matters who is leading the country that is under attack and how its leader chooses to respond. As modern history has amply demonstrated, the greatest conflicts, and their outcomes, have often been shaped as much by personal leadership as by objective factors such as resources or military strength.”

Churchill was far from perfect. He was self-righteous, bombastic, head strong man, prone to bouts of severe depression — his famous ‘black dog’ — , an alcoholic, and was arguably racist in many of his views; but, had someone other than Churchill been appointed Britain’s eve of war leader then the last century of European, if not world, history may have looked remarkably different, likely remarkably darker, remarkably less free.

It’s not too much of a stretch to say that war made Churchill, or to put it another way, Hitler made Churchill the great leader that Britain, and arguably Europe, needed at that time.

In much the same way Putin can be said to have made today’s great wartime leader, Volodymyr Zelenskyy.

Until Putin launched his invasion Zelenskyy had been an undistinguished leader. An inexperienced leader, hesitant, often times naive and sometimes out of his depth politically, Zelenskyy, like Churchill before him, has been made by the expansionist actions of an aggressive, imperialist dictator.

On February 24th as Russia began its cruel, callous and ultimately pointless invasion of Ukraine I asked ‘In a time of grave crisis, where (was) the West’s Winston Churchill?

Up until that point the West’s response to Putin’s aggression had been muted and weak, and I wasn’t alone in wondering from where would the West respond effectively. Who exactly was going to stand up to Putin once he had sent his forces into Ukraine.

Since then one man has become a hero, not just to his own Ukrainian people, but around the world. Comparisons with Winston Churchill have been widespread, especially since he invited such comments by invoking the famous “We’ll fight them on the beaches…” words of Churchill in a speech made to the British parliament on March 8th.

A strong leader leading a strong people. This is Ukrainian President Volodymyr Zelenskyy.

And now, just over a month into the war, as Ukrainian forces appear to have gone on the offensive, decapitating many frontline Russian units, and forcing the uninvited invaders back in towns like Mikolaiv in the South, Makariv to the West of Kyiv, Irpin and Bucha, two suburban towns of Kyiv, and possibly even in Kherson, the first major metropolis captured by the Russians, where the Ukrainians are on the front foot for the first time.

The effect appears to have further weakened the morale and resolve of many troops, with some possibly even turning on their own commanders, or even sabotaging their own equipment, in frustration as their losses mount. So bad has it become in fact that Putin has ordered his military chiefs to refocus their attention on securing the breakaway Donbas regions in the East of Ukraine.

Russia’s enemies elsewhere, in this case the Azerbaijanis, are taking advantage of a distracted, weakened and poorly performing military by moving troops into the disputed regions of Nagorno-Karabakh to face down Armenian troops, normally supported by Russia.

In every sphere things are not going Putin’s way, but that said, this war is far from over.

“Cometh the hour, cometh the man…”

As the Russian forces begin to pull back in some areas, possibly to regroup ahead of another offensive, or possibly to concentrate their efforts as suggested, on the Donbas regions, Zelenskyy continues to rally his troops and garner support and admiration from around the globe.

In sharp contrast to Putin, who would appear to be even more isolated now than ever, Zelenskyy circle is widening.

This is surely the very opposite effect that Putin would have expected on the eve of the invasion. Much like Hitler, who thought of the British as a like-minded people who would respond favourably to his overtures (2, 3,), Putin has badly misunderstood the character and desires of the people they would dominate.

Conjecture about what ‘might have been’s’ is a largely fruitless and empty exercise. If Hitler had not been the German Chancellor. If the Allies had not imposed such harsh reparations on Germany at the end of WWI. If Lord Halifax and not Churchill had been made PM in 1940. If Yeltsin had actually been impeached and Primakov had succeeded him as Russian leader, and not Putin. If Zelenskyy had fled and ‘took the ride’ and not ‘the ammunition.’

Cliff Gladwin, a post-WWII Derbyshire cricketer said ‘Cometh the hour, cometh the man,’ and whilst in the cases of both Churchill and Zelenskyy, the hour was decided by a vicious dictator bent on destruction, they both stood up to inspire when the hour called for a leader to do just that.

Thanks for reading.

  1. My Early Life; Winston Churchill, 1930.
  2. Churchill; Roy Jenkins, 2001.
  3. Hitler; Ian Kershaw, 2009.



Peter Winn-Brown

The past can illuminate the present if we shine the light of inquiry openly, truthfully, with attention to detail & care for the salient facts.