Warren Buffett 'Won Everything' Playing Games With Sister Growing Up: Did His Monopoly Strategy Change With Investing?

Warren Buffett will step down as the CEO of Berkshire Hathaway Inc BRKBRK at the end of 2025, leaving behind a legacy of investment success.

In a May 2024 interview, Buffett’s younger sister Bertie Buffett Elliott, shared insights into their childhood and her brother’s rise to success.

Despite Warren’s stature as one of the world’s most revered investors, to Bertie, he remains simply “my big brother.”

Bertie reminisced about their competitive childhood, where Warren’s love for winning was evident from an early age.

“We played everything from ping pong to cards to Monopoly to boxing… and he won everything,” Bertie recalled to CNBC in May 2024.

Yet, despite Warren’s constant victories, Bertie never lost her desire to keep competing.

“For some reason, it didn’t bother me. I still wanted to play. You know, I was always hoping for a win.”

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Buffett and Monopoly: Elliott’s recollection of their Monopoly games offers a window into Warren’s early strategic mindset. While Bertie was happy “hoarding the money in little piles,” Warren’s approach of acquiring properties paid off in the end. “All my money was gone,” she said, laughing. “I realized too late that it was a better strategy to buy property than hoard the money.”

Followers of Buffett might view his style of play in Monopoly as the reverse of investing, as the legendary investor often saves his cash until the right investment opportunity arises, rather than buying up everything in sight.

Despite the sibling rivalry, Bertie joked that her endless losing streak helped shape Warren into the winner he is today. “I trained him to be a winner because since he was winning all the time playing against me… he owes his great success to the fact that I trained him to win.”

Bertie’s playful take on their childhood games highlights the unassuming origins of Warren Buffett’s competitive spirit, which later helped him conquer the world of finance.

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This article was previously published by Benzinga and has been updated.

Image created using artificial intelligence via Midjourney.