At the time, Forbes estimated that Trump was worth $3.1 billion. In other words, despite all of the speculation to the contrary, he had apparently outperformed the market index by about $1 billion, as of 2018. That accomplishment didn’t get anywhere near as much coverage as the previous suggestions that Trump had underperformed the market.

Trump continued to stay comfortably ahead of the S&P 500 until last year, when Covid turned the world upside down. The stock market tanked, and Trump personally lost an estimated $1 billion in a matter of weeks. After the initial shock, the overall market began to recover, but Trump’s fortune languished. With his hotels, storefronts and office buildings hollowed out, the S&P 500 started to catch up to Trump. Eventually, in early 2021, the market overtook the mogul for good.

By September, when Forbes locked in its estimates for its annual list America’s richest people, Trump’s net worth stood at an estimated $2.5 billion, which, for the first time in 25 years, left him short of the cutoff for The Forbes 400. If Trump had instead lived a simple life and invested in the S&P 500 for decades, he would have been worth an estimated $3 billion, enough to rank No. 377. Instead, he had decided to go his own way, providing him with years as a high-stakes businessman, decades as a famous name and one term as the president of the United States—but eventually costing him hundreds of millions.