Playing To Win

Winning the Long Game of Strategy

Don’t Let the Short Game Blind You

Roger Martin
6 min readJul 18, 2022


Source: Roger L. Martin 2022

This piece is spurred by the events in Ukraine, which are tragic for the people of Ukraine — all of them, whether east, west, south, north, or in exile. Vladimir Putin, with his indiscriminate and unapologetic bombing of innocent civilians, has become the latest reminder that periodically the ultimate manifestation of evil will be found walking among us on the planet. As with the vast majority of humanity, I hope this saga ends up with Ukraine providing a great illustration of successfully playing the long game in strategy. To that end, I decided to write my 38th Year II Playing to Win/Practitioner Insights (PTW/PI) piece on Winning the Long Game in Strategy: Don’t Let the Short Game Blind You. You can find the previous 90 PTW/PI here.

Some Personal Background

Like pretty much everyone who has taken a philosophy course, I was taught the Melian Dialogues, ancient Greek historian Thucydides’ account of the 416 BC siege of Greek Island Melos by the then-dominant Athenian armed forces. The Athenian military representatives insisted that Melos submit to Athenian rule or be annihilated. Faced with what appeared to be the unacceptable choice of subjugation, Melian leadership chose resistance. The dominant Athenian force simply surrounded the island with its enormous fleet and in due course, the Melians, with starvation looming, surrendered.

In response, the Athenian conquering forces executed all the adult Melian males and sold the Melian women and children into slavery around the Athenian empire.

The ‘lessons’ always grated on me. The purported ‘right answer’ always seemed to be that the Melians were right to have fought for their independence and the Athenians were inhumane because they executed the adults and enslaved the rest. While the latter is arguably correct, the former never sat well with me.

Playing the Long Game

I have always believed that the Melians played the short game. They viewed their choice in short game terms: surrender now and be ruled by a foreign power, or fight and risk almost certain defeat. Neither of the (seemingly only possible) choices was at all attractive. Forced to choose, they chose the lessor of two evils.

No. They had the choice to play the long game. They had the option of continuing the Melian culture and waiting for the time to stand and fight — but only when they had a chance to win.

They exterminated that chance from ever being realized. When the Athenians executed the adults and spread the Melian women and children to the wind as slaves, all that was left was the physical place, the island of Melos. That isn’t enough from which to build back. It was over.

The modern analog is Eastern Europe. In the wake of World War II, numerous Eastern European states were faced with the overwhelming force of the Soviet Union combined with the indifference of the Allies. The war had taken a terrible toll on every nation involved and the Allies didn’t have the will to fight further. Hence, there was nobody to help when the Soviet Union flexed its domineering muscles.

That produced four decades of subjugation of the small nations, who came to be known as Soviet Bloc countries, by a large and powerful nuclear superpower. While there were several notable uprisings — including Hungary in 1956 and Czechoslovakia in 1968 — any attempt to counter the Soviet Union’s power was crushed.

But in due course, the Soviet hegemony in the region showed cracks and in 1989, the Berlin Wall came down and beginning in 1991 former Soviet Bloc countries including Ukraine became independent. However, much to the chagrin of Soviet nationalists like Putin, Ukrainian parents played the long game and taught two generations of children what it meant to be Ukrainian and that they should despise their Russian/Soviet oppressors.

Nothing about either subjugation or subsequent independence was easy and the oppressors, now led by Putin struck again in 2014, invading and annexing Crimea. As with the wake of World War II, Ukraine didn’t make a full-scale attempt to defend, again was let down by its democratic allies.

But when Putin returned in 2022, this time to retake all of Ukraine and fully subjugate it as with puppet Belarus, Ukrainian President Volodymyr Zelensky decided that standing and fighting wasn’t a lost cause — even though many observers initially judged it to be just that. Western democracies were again pretty much ineffectual at the beginning of the invasion, leaving Ukraine to fend for itself, which it did admirably. But thankfully, in due course, they began to support the besieged democracy and it appears that Putin’s goal of extinguishing Ukraine has been thwarted.

Whether Zelensky can take back the east remains in the balance — I dearly hope he can because allowing pure evil to triumph is bad for humanity as well as those in eastern Ukraine.

But unlike the Melos, Ukraine has played the long game of strategy and has a country and a culture to show for it.

The Long Game in Business

An analogous thing happens in business. I say ‘analogous’ not ‘identical’ because millions of lives aren’t at stake. But similarly, to protect possibilities, the long game needs to be played.

Take, for example, the case of PayPal. Founded through a series of initiatives in the 1998–2000 period, PayPal went public in 2001. But in 2002, it was acquired by eBay, at the time a giant in comparison. Could have PayPal fought the acquisition? It probably didn’t want to, but probably couldn’t if it had wanted to.

It never belonged within eBay — a single auction/ecommerce platform. PayPal was a payment platform that needed the broadest possible user base to survive and thrive. Under activist pressure (yes, sometimes the activists have a real business rationale, not just craven monetary goals — not often, but sometimes), in 2014 eBay announced the intention to spinoff PayPal, which was completed in 2015.

Fortunately, PayPal management played the long game and maintained the heart and essence of PayPal’s strategy while under 13 years of eBay control — a very long time in the business world. And it has prospered wonderfully as an independent company. Across its six years (2015–2021) as a newly independent company, PayPal has grown revenue at a 18.4% compound annual rate (CAGR) and profit at a 22.6% CAGR.

PayPal didn’t object to or fight its takeover by eBay. But in the modern world of business, most unwanted takeovers take place through activist private equity campaigns. It is real challenge for leadership of an assailed business to play the long game of strategy. Some great companies, like Toys ‘R Us and iHeartMedia collapse under the weight of the debt forced onto their balance sheets by their careless masters. Others are terminally wrecked by the conceit of financial engineers who think they can also manage a real company — like Eddie Lampert at Sears or Bill Ackman at JC Penney. Other targets are broken into pieces, ending their existence as the entity that the world knows, such as General Electric after concession to the desires of Nelson Peltz. In some cases, a split may be a good thing — but when activists are involved, it certainly isn’t consensual.

The leadership task is to play the long game and keep the essence of the company alive and well to continue its culture and legacy, something P&G managed to adroitly do through the four-year reign of Peltz’s Trian Partners. It is a tough battle that is more often lost than won: it requires courage and commitment through often trying times.

Practitioner Insights

Time is an extremely important strategic dimension that should never be underestimated or overlooked. What is fully impossible today might well be feasible tomorrow. Utilize the time dimension strategically to make possible in the future an outcome that is not possible today. Don’t make a choice today that will eliminate the possibility of a choice that you would wish to make later — unless of course you absolutely must. In many cases, time can be your ally if you exploit it thoughtfully.

Don’t play a short game when there is no positive short term alternative. When faced with such a situation, ask what alternative might be made possible by playing the long game? It is better to keep the faith alive and give yourself a chance to fight for the future than to fight a battle today that will destroy your chance of reemerging. And if you play the long game, it is critical to keep alive and vibrant the essence of who you are, whether that is the essence of Ukraine, PayPal, or P&G.



Roger Martin

Professor Roger Martin is a writer, strategy advisor and in 2017 was named the #1 management thinker in world. He is also former Dean of the Rotman School.