The scale of Goldman’s feat was remarkable, but Ballmer was just one client pursuing such a strategy. The tax savings from these losses amount to at least $138 million. ProPublica estimates that from 2014 through 2018, Ballmer was able to generate tax losses totaling $579 million without changing his investment portfolio in a meaningful way. Similar efforts that December brought $26 million more. A month later, he did it again, landing at least $23 million in tax-reducing losses. Over and over, Ballmer sold and bought stocks in roughly equivalent amounts, as on that July day, when he swapped around $200 million worth. His losses secured, Ballmer was ready to catch the bounce back. But well-tuned software could easily find the right stocks to keep the accounts tracking the market. Sometimes, the replacements were nearly identical securities, as with Shell and BHP.

When, inevitably, some of the stocks underperformed or the whole market dipped, Goldman was ready to pounce, selling off the losers and replacing them with equivalents. Over time, the markets, as they had historically, would buoy Ballmer’s investments upward. At Goldman, the hundreds of stocks in Ballmer’s “Tax Advantaged Loss Harvesting” accounts were selected to follow the movement of the broader markets. Ballmer’s not-so-bad day, in fact, was carefully planned, part of a strategy by Goldman Sachs, which conducted the trades on Ballmer’s behalf, to wield the stock market’s natural volatility to the billionaire’s advantage.

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