Even Legendary Investors Struggle Sometimes
In investing, top money managers are often portrayed as being run by brilliant minds who outsmart the market year after year, delivering big returns no matter what.
But this expectation is an illusion because markets are shaped by unpredictable forces such as geopolitical shocks, policy changes, and “black swan” events that even the best money managers can’t always avoid. Therefore, even the most legendary fund managers have losing years.
Ray Dalio
Ray Dalio, founder of Bridgewater Associates, the world’s largest hedge fund with over $100 billion under management. Dalio’s “Pure Alpha” strategy, built on macroeconomic insights and risk-parity principles, has produced legendary long-term results. Yet even Bridgewater has stumbled. It’s previously had drops of about 16% in one month alone.
Bill Ackman
Bill Ackman provides another example. in 2014, Pershing Square soared 40%, and in 2020, Ackman turned a $27 million hedge against COVID-19 market risk into a $2.6 billion gain, one of the most profitable single trades in hedge-fund history. But 2015 was brutal: Pershing Square lost 20.5%, largely due to an overconfident stake in Valeant Pharmaceuticals. The pain continued into 2016 with another 13.5% loss, leading Ackman to publicly reflect on the dangers of conviction turning into stubbornness.
George Soros
George Soros, whose Quantum Fund famously “broke the Bank of England” in 1992, endured his own losing streaks. Few names in finance command as much respect as George Soros, the founder of the Quantum Fund and one of the most successful money managers in history. Over several decades, Soros delivered average annualized returns exceeding 30%. However, he’s suffered as much as 22.9% annual losses.
Said Haidar
In April 2025, Said Haidar’s flagship Jupiter macro fund plunged roughly 25%, marking one of the worst monthly losses in its 20+ year history. The carnage follows a brutal two-year stretch: in 2023, the fund lost over 43%, and in 2024 it tumbled again by about 32–33 %. Despite its recent struggles, Haidar Capital’s Jupiter Fund remains one of the most remarkable macro hedge funds of the past two decades. The fund has historically delivered extraordinary gains. For example, Jupiter surged 193% in 2022, one of the best performances in the entire hedge-fund industry that year, as its aggressive bets on rising interest rates and surging energy prices paid off spectacularly.
Peter Lynch
Perhaps the most instructive lesson comes from Peter Lynch, who managed Fidelity’s Magellan Fund. Lynch delivered a staggering 29.2% annualized return. His “buy what you know” mantra turned Magellan into a household name, outperforming the market in 11 of his 13 years.
Yet the average investor in his fund earned just 7% per year and many lost money. Why? Because they bought after strong years and sold after weak ones. They tried to time his fund instead of staying invested.
Even The Best in the World Lose Money Sometimes
Today, everyone is obsessed with instant gratification, but for investors, the lesson is clear: expecting a hedge fund to deliver massive profits every single year is unrealistic. Great investing is a long game of patience. The most successful investors stay committed through cycles.