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Who played the ‘most expensive joke’ on Anand Mahindra, the fallible chess player?

Comedian Samay Raina challenged Anand Mahindra during an online interaction in 2020 to create a global chess league. Mr Mahindra took him seriously. “Usually, comedians provoke laughter but Samay in a way provoked a global chess league,” said Anand Mahindra, Chairman of the Mahindra Group, Mahindra & Mahindra Ltd and Tech Mahindra Ltd, speaking at […]

By deepak · September 6, 2026 · 3 min read

Comedian Samay Raina challenged Anand Mahindra during an online interaction in 2020 to create a global chess league. Mr Mahindra took him seriously.

“Usually, comedians provoke laughter but Samay in a way provoked a global chess league,” said Anand Mahindra, Chairman of the Mahindra Group, Mahindra & Mahindra Ltd and Tech Mahindra Ltd, speaking at the fourth season of the Global Chess League in Bengaluru. Four seasons later, the challenge has become a Tech Mahindra-FIDE joint venture with a $1-million annual prize purse and a projected five-year business value exceeding $40 million.

“If it is a joke then it’s the most expensive joke anyone has ever played on me,” Mahindra said. And he appears happy to be on the receiving end. “I’m in fact enjoying the fruits of the success of that expense and effort.”

There was reason to take a comedian seriously. Mahindra had been watching Raina and chess commentator Sagar Shah stream the 2020 Chess Olympiad and noticed their audience swelling. “I saw that in every 15 minutes the crowd of people watching grew larger,” he recalled.

Then the joke attracted some serious company. FIDE President Arkady Dvorkovich “somehow got hold of my email” and asked whether Mahindra was serious about starting a league. He was. Months of conversations followed. Viswanathan Anand, India’s five-time world champion, then “unhesitatingly” came aboard.

The league now has six franchises and has travelled from Dubai to London, Mumbai and Bengaluru. A comedian supplied the provocation, Mr. Mahindra spotted the audience, and some of chess’s biggest names helped turn the punchline into reality.

The joke may have created a league of grandmasters. It hasn’t made Mahindra one.

“I personally feel the effects of that loss every day as I battle the bots on chess.com and I’m brutally mocked for making blunders,” he said.

Mahindra consoles himself that his defeats make a small contribution to ensuring that the “vulnerable, the fallible human element is kept alive in the game of chess.” He even enjoys seeing grandmasters occasionally blunder because, he said, it makes them “endearing and more like us, fallible as it were.”

Bengaluru offered an apt backdrop. Long before today’s AI boom, chess was a test of whether machines could match human intelligence. Machines won that battle, but Mr Mahindra argues that perfection isn’t why people watch chess.

“We gather not to watch machines play. We gather to watch human beings play,” he said .“A machine can tell us what the best move is but it’s only people who make us care about it.”

Perhaps that is why the “most expensive joke” still makes Mahindra laugh. A comedian made the opening move, an industrialist played along, and a global chess league followed.

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