‘If it is a joke, then it is the most expensive joke anyone has ever played on me’: How Samay Raina’s challenge led Anand Mahindra to launch a chess league

Devendra Pratap Singh

September 8, 2026


'If it is a joke, then it is the most expensive joke anyone has ever played on me': How Samay Raina’s challenge led Anand Mahindra to launch a chess league

A comedian made a casual suggestion. A businessman took it seriously. And a few years later, the result was a global chess league.Anand Mahindra has revealed the rather unexpected story behind the Global Chess League, tracing its beginnings to a challenge from comedian Samay Raina during an online interaction in 2020.Mahindra jokingly calls it the “most expensive joke” ever played on him. But what started as a suggestion eventually turned into a major international chess competition involving some of the biggest names in the sport.Speaking at the fourth season of the Global Chess League in Bengaluru, Mahindra recalled watching Raina and chess commentator Sagar Shah stream the 2020 Chess Olympiad. What caught his attention wasn’t just the game itself, but the number of people tuning in.He noticed that the audience was growing rapidly as the stream went on. That made him wonder whether chess could be presented in a way that reached a much bigger audience.Around the same time, Raina challenged Mahindra to start a global chess league, as reported by Business Line.Mahindra could have simply laughed it off. Instead, he decided to see where the idea could go.

From a challenge to a real league

The suggestion soon moved beyond an online conversation. FIDE president Arkady Dvorkovich reached out to Mahindra to find out whether he was actually serious about starting a league.He was.What followed were months of discussions, eventually bringing five-time world champion Viswanathan Anand into the project as well. With Anand and Dvorkovich involved, the idea began to take a much more concrete shape.The Global Chess League was eventually launched as a franchise-based team competition. Rather than focusing only on individual players, the format puts some of the world’s top chess stars into teams, giving the sport a different kind of competitive setting.The league has since been held in cities including Dubai, London, Mumbai and Bengaluru, and features six franchises.Four seasons on, it has grown considerably from the idea that began with Raina’s challenge. The league has an annual prize purse of $1 million, while its projected five-year business value is expected to cross $40 million.No wonder Mahindra refers to it as the “most expensive joke” anyone has played on him.“If it is a joke then it’s the most expensive joke anyone has ever played on me,” he said.But he clearly doesn’t see the money and effort as something to regret.“I’m in fact enjoying the fruits of the success of that expense and effort,” Mahindra added.

Mahindra still gets beaten by chess bots

Mahindra’s connection with chess isn’t exactly that of a grandmaster. In fact, he has openly admitted that he still struggles against chess bots on Chess.com and gets plenty of teasing over his mistakes.But losing games hasn’t made him any less interested in the sport. If anything, it has shaped how he looks at chess and its growing relationship with technology.With artificial intelligence now capable of calculating moves far beyond what most humans can manage, Mahindra believes the real appeal of chess isn’t simply about finding the perfect move.It’s about watching a person make the move.“We gather not to watch machines play. We gather to watch human beings play,” Mahindra said. “A machine can tell us what the best move is but it’s only people who make us care about it.”And that’s what makes the story of the Global Chess League particularly fitting. A challenge from a comedian helped spark the idea, but Mahindra’s willingness to take it seriously turned a casual suggestion into a league built around the most unpredictable part of chess – the people playing it.



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