This analysis began, as many serious historical investigations do, because I wanted to beat my children in the games we play.
I had been reading The Art of Strategy, Avinash Dixit and Barry Nalebuff's wonderful book on game theory, and came across a simple idea about sequential games:
Look forward. Reason backward.
Naturally, my first instinct was not to apply this to investing or corporate strategy. I used it against Neil and Malhaar.
For a brief and glorious period, I kept winning.
This produced two consequences. First, my children became suspicious and stopped playing with me. Second, I started thinking about Chhatrapati Shivaji Maharaj.
I come from Satara, the later capital of the Maratha empire. I grew up worshipping Chhatrapati Shivaji and have studied his life for years. But suddenly the familiar stories looked different. Chhatrapati Shivaji was the weaker player in most of his encounters - yet came out on top in a remarkable proportion of those that really mattered.
So, I wondered: What if we stopped explaining this through bravery, ingenuity or luck?
What if Chhatrapati Shivaji was exceptionally good at designing the game itself?
There is no better example than the Battle of Pratapgad — where a relatively inexperienced, 29-year-old Shivaji Maharaj commanding roughly 5,000 men comprehensively defeated Afzal Khan, a powerful general commanding roughly 22,000.
The standard explanation makes Afzal's defeat seem almost inevitable: he allowed himself to be drawn into difficult terrain, progressively separated from his army and walked into Chhatrapati Shivaji's trap.
In hindsight, his decisions can look almost inexplicable.
Except, one by one, they weren't.
Let's see for ourselves.
1659
Chhatrapati Shivaji Maharaj is a young local chieftain with the inconvenient idea that he should have an independent Hindu kingdom of his own — Hindavi Swaraj. Sultan Adilshah of Bijapur disagrees. Not intellectually. He concludes the problem needs professional attention. He summons his chief business officer.
Enter Afzal Khan. Around 55, an experienced general, physically enormous — supposedly 6½ feet tall — with the full backing of the Bijapur sultanate. In his acceptance speech, Afzal boasts he will bring Chhatrapati Shivaji back to Bijapur, dead or alive, without even getting off his horse.
This is roughly the 17th-century equivalent of promising the board that the deal will close by quarter-end.
Chhatrapati Shivaji has nothing comparable. About 5,000 men. Limited resources. Limited military experience. And, by all accounts, about a foot shorter than Afzal.
So, what are Chhatrapati Shivaji's choices?
Fight in the open? Lose for sure. Run? Survive, perhaps — but cremate the dream of Hindavi Swaraj. Stay inside the fort? Watch Afzal devastate his territory while his commanders slowly reconsider their career choices.
There is no obvious winning move.
Except, given the history of Afzal in the humiliating arrest of his father (Shahaji Raje) and role in the death of his elder brother (Sambhaji Raje), Chhatrapati Shivaji wasn't looking for the next move. He had already decided the endgame:
Kill Afzal. Survive the encounter. Break his 22,000-man army.
Afzal was not going back to Bijapur. Period. The only question was how to engineer that outcome. Start with the endgame. Then reason backward.
First, geography
Afzal's preferred solution is simple: get Chhatrapati Shivaji onto an open battlefield and let numbers settle the matter.
Chhatrapati Shivaji effectively says: Not interested. He parks himself at Pratapgad, surrounded by thick forest.
Afzal tries to force him out by desecrating prominent temples, including Tulja Bhavani. Thank God there was no Instagram then — the reels would have made it considerably harder not to respond. Yet, Chhatrapati Shivaji refuses to be drawn out.
Afzal then tries to break the local strongmen supporting Chhatrapati Shivaji through threats and incentives. Chhatrapati Shivaji focuses on keeping the critical ones loyal, notably Kanhoji Jedhe. Kanhoji's decision has signalling value: if the man who best understands the local situation is prepared to put his family at risk backing Chhatrapati Shivaji, that itself is information. Loyalty becomes contagious. Chhatrapati Shivaji had, in effect, secured his anchor investor. The rest of the syndicate followed.
Meanwhile, time is passing. Afzal's promise to close without getting off his horse is ageing badly. Two quarters gone. Deal not closed. The board back in Bijapur is getting restless. Somewhere in Afzal's camp, his EA (executive assistant) is preparing a one-pager explaining why the horse comment was taken out of context.
Afzal proposes a meeting.
Afzal activates Plan B: settle the issue through a personal meeting. There is logic to this — he has killed a king, Kasturi Ranga, at exactly such a meeting before.
And here the story gets more interesting. As the option of fighting on the open field is off the table, from Afzal’s perspective as well, the endgame would be:
Get Chhatrapati Shivaji out of the fort. Get him alone. Get him within reach. Capture or kill him. End the rebellion.
So, both men wanted essentially the same position — a personal meeting, face-to-face, within striking distance. Afzal wanted it because proximity neutralised Shivaji's forts and brought the rebel within his grasp. Chhatrapati Shivaji wanted it because proximity neutralised Afzal's 22,000 men and brought Afzal within his.
Each believed the meeting favoured him. Neither wanted to walk away from it. Game theorists have a name for such a position — an equilibrium: neither player deviates, because each is convinced it maximises his own chances.
Both thought they were getting the other exactly where they wanted him. That is the game.
Chhatrapati Shivaji accepts. But through his emissary, he keeps signalling fear. From Afzal's perspective, this is excellent news. You marched 22,000 men specifically to intimidate this rebel. He now appears intimidated. The strategy is working.
Shaping the board
They negotiate the venue. Afzal proposes Wai, where he is camped on the plains. Chhatrapati Shivaji proposes Pratapgad. The message: Chhatrapati Shivaji is terrified. He regards Afzal as a father figure. Afzal should come, take this recalcitrant child by the finger and lead him back to Bijapur. And he is welcome to bring his army — Chhatrapati Shivaji will arrange for its travel and comfort.
Why should Afzal refuse? Twenty-two thousand men are enough even in difficult terrain. He had governed the area for 10 years. And Prataprao More, a local commander who knew the terrain like the palm of his hand, had joined him. Afzal effectively had Google Maps.
He agrees. Rational.
Both men come essentially alone. Ten bodyguards each, kept an arrow's distance away. Perfectly fair.
From Afzal's perspective, what is the downside? If the meeting is peaceful, he gets Chhatrapati Shivaji within reach. If it isn't — 10 against 10, and he is an enormous, powerful man. If this little fellow tries anything clever, I'll squash him with my bare hands. And his army is nearby.
Agree. Entirely rational.
Meanwhile, Chhatrapati Shivaji's men clear paths to facilitate the movement of Afzal's army. Perfect hospitality. Except the felled trees can later block specific routes — and the presence of Chhatrapati Shivaji's men along the way has already been explained. Afzal's army moves along the route Chhatrapati Shivaji wants and camps where Chhatrapati Shivaji wants. A curated experience.
The meeting is fixed for 10 November 1659. A grand shamiana is erected — in direct sight of Chhatrapati Shivaji's forces on the fort, with no line of sight from Afzal's camp. What Afzal's army can see has been thought about. More importantly, so has what it cannot see.
Today, we would call this information architecture and commission a 74-page PowerPoint. Chhatrapati Shivaji deployed men behind trees.
One Thousand Musketeers
Then something interesting happens. Chhatrapati Shivaji's emissary discovers Afzal has prepared 1,000 musketeers to accompany him. Afzal has spotted the risk and tried to muscle his way through.
The emissary pleads: Chhatrapati Shivaji is terrified. If you arrive with 1,000 armed men, he won't even come down.
Now Afzal faces a perfectly sensible trade-off. The musketeers make him safer — but they reduce the probability that Chhatrapati Shivaji turns up, which defeats the purpose of the meeting. He leaves them midway. Rational.
At the venue, Afzal keeps one man close: his formidable swordsman, Sayyad Banda. Chhatrapati Shivaji sees this from a distance and waits. The emissary returns - Chhatrapati Shivaji is terrified of Saiyad; please ask him to stand with the other nine. And crucially — Chhatrapati Shivaji's ten are being kept at exactly the same distance. Ten versus 10. Same distance. Same rules. Fair.
Afzal agrees.
Both get what they want .
At this point, Afzal thinks his plan has worked. Chhatrapati Shivaji is coming out of his fort. He is coming essentially alone. He is coming within touching distance. This is precisely the end-position Afzal wanted.
It is also precisely the end-position Chhatrapati Shivaji wanted.
Afzal thought he had persuaded Chhatrapati Shivaji to come close enough to be killed. Chhatrapati Shivaji had persuaded Afzal to think exactly that.
While Afzal knew his own endgame, he probably did not anticipate Chhatrapati Shivaji's. What he could see — 10 against 10, equal distance, his army nearby — was scrupulously symmetrical. What he could not see — the concealed armour, the bodyguard assignments, the hidden Maratha forces, the controlled routes, the signalling architecture and everything designed to happen after the meeting — was not.
The visible game was fair. The actual game was over.
The Meeting
Afzal comes prepared for offence: a concealed dagger, no armour — masking intent, signalling fearlessness. He does not expect Chhatrapati Shivaji to move first.
Chhatrapati Shivaji comes prepared for both defence and offence. He assumes Afzal may get the first move — so he designs his equipment to keep the game alive after it. Concealed armour. A bichwa (curved dagger) and tiger claws.
Afzal packed for a murder. Chhatrapati Shivaji was prepared for a murder that might initially go badly.
The meeting degenerates quickly. Afzal embraces Chhatrapati Shivaji, traps his neck and strikes with the dagger. The armour does its job. Chhatrapati Shivaji survives the first move — and immediately counters. Chhatrapati Shivaji sustained a wound on his head from this encounter, but was saved due to the steel cap he had worn inside.
Sayyad Banda rushes in. Jiva Mahale kills him. A melee follows. All 10 of Afzal's bodyguards die. Chhatrapati Shivaji loses none.
Ten–nil is an unusual score for spontaneous chaos.
Afzal's 10 were there in case something happened.
Chhatrapati Shivaji's 10 were there because something was going to happen.
Same numbers. Same distance. Same rules.
Different information.
Jiva Mahale's key performance indicator (KPI) was wonderfully simple: Sayyad Banda. When Afzal screams in pain, Sayyad must understand what happened, identify the source of the threat and react. Jiva doesn't. Sayyad watches Chhatrapati Shivaji. Jiva watches Sayyad. One is reacting. The other is executing. Chhatrapati Shivaji seemed to have created a perfect counter for each of the bodyguards Afzal had with him, effectively using man-to-man marking.
Afzal dead. Now what?
This is where the two endgames truly diverge. Afzal's plan was concentrated on one objective: get close, strike, win. Chhatrapati Shivaji's endgame was larger: kill Afzal, survive, break his army. A dead Afzal with Pratapgad surrounded by an organised 22,000-man army would still be a disaster. So, the second half was already designed.
The man with the horn near the shamiana had one KPI: See action? Blow horn. The cannon crew: Hear horn? Fire cannon. The commanders in the forest: Hear cannon? Attack.
Nobody needed to know what happened inside the shamiana. Who struck first? Which weapon? Fascinating questions for historians. Completely irrelevant to the fellow waiting in the forest. Cannon fired? Attack.
No WhatsApp group instructions. No "Can someone confirm?"
More importantly, no meeting to discuss the outcome of the meeting.
Afzal's army had precisely the opposite problem. Their commander had gone for a meeting. Now cannons were firing. Ceremonial blasts — or a signal? Before they could figure it out, they were under attack. Some troops were already retreating. Did they know something? Confusion itself became information. The army unravelled.
The 22,000 men didn’t disappear. But they were rendered irrelevant at the crucial juncture.
Notice, too, that Chhatrapati Shivaji's plan had layers. It was not dependent on everything going perfectly. Afzal strikes first? Armour. Sayyad intervenes? Jiva. Melee. Horn, cannon, attack. Afzal's plan depended on its first move succeeding. Chhatrapati Shivaji's could survive several things going wrong and still move towards the outcome he wanted. As a last resort, he had left clear instructions on succession and resistance in case he got killed in the encounter.
The Whole Game
Imagine Chhatrapati Shivaji making the complete proposal to Afzal at the beginning:
Please enter terrain of my choosing. Bring your army along routes prepared by my men and camp where I want. Leave your entire army behind. Bring 10 bodyguards. Keep your best swordsman an arrow's distance away. Enter a pavilion your army cannot see.
Then stand within touching distance of me.
Afzal would have declined. Possibly impolitely.
But nobody ever asked him to agree to the endgame. He only had to agree to the next move. And every next move made sense.
And here is the fascinating part: Afzal actually wanted the last sentence.
He wanted Chhatrapati Shivaji within touching distance every bit as much as Chhatrapati Shivaji wanted him there. The personal meeting was never Afzal making some inexplicable mistake. It was the point at which both men's strategies converged — the equilibrium they had each reasoned their way to.
The difference was everything Afzal couldn't see around that position. He knew his plan. But did not anticipate Chhatrapati Shivaji's. And Chhatrapati Shivaji had spent every preceding move shaping what Afzal saw, what he believed and ,therefore, what remained rational for him to do.
So, the lesson is richer than simply look forward, reason backward.
The deeper game was—understand the endgame your opponent wants — and see whether his rational path towards it can be made to lead instead towards yours.
My children eventually figured out what I was doing and stopped playing with me.
Afzal Khan didn't get the chance.
#GameTheory #Strategy #ChhatrapatiShivaji
PS - Pratapgad is only the first. I plan to look at some of the other defining episodes in Chhatrapati Shivaji's life through the same game-theory lens.
(An investor and leader focused on building scalable, climate-aligned platforms across sectors, Rohit Talwalkar is the managing director of Eversource Capital.)
looking forward to more such articles.