In its technological innovation, Standard Oil was the Google of its day. The company’s founder, John D. Rockefeller, had become the richest man in America by spending millions of dollars hiring scientists to transform how oil was refined and transported. And those innovations earned the public’s admiration. In 1858, before Standard Oil was founded, lighting a home required whale oil, which cost up to $3 a gallon, putting illumination out of reach for all but the wealthiest of households. By 1885, after Standard Oil figured out how to refine kerosene, it cost just 8 cents a gallon to brighten the night. “Let the good work go on,” Rockefeller wrote to a partner. “We must ever remember we are refining oil for the poor man and he must have it cheap and good.”

Standard Oil’s technological discoveries gave the company huge advantages over its rivals, and Rockefeller exploited those advantages ruthlessly. He cut secret deals with railroads so that other firms had to pay more for transportation. He forced smaller refineries to choose between selling out to him or facing bankruptcy. “Rockefeller and his associates did not build the Standard Oil Co. in the boardrooms of Wall Street,” wrote Ida Tarbell, a muckraking journalist of the day. “They fought their way to control by rebate and drawback, bribe and blackmail, espionage and price cutting, and perhaps more important, by ruthless, never slothful efficiency of organization.”

In 1906, President Theodore Roosevelt ordered his Justice Department to sue Standard Oil for antitrust violations. But government lawyers faced a quandary: It wasn’t illegal for Standard Oil to be a monopoly. It wasn’t even illegal to compete mercilessly. So government prosecutors found a new argument: If a firm is more powerful than everyone else, they said, it can’t simply act like everyone else. Instead, it has to live by a special set of rules, so that other companies get a fair shot. “The theory was that competition is good, and if a monopoly extinguishes competition, that’s bad,” says Herbert Hovenkamp, co-author of a seminal treatise on antitrust law. “Once you become a monopoly, you have to start acting differently, and if you don’t, then what you’ve been doing all along starts breaking the law.”

The Supreme Court agreed and split Standard Oil into 34 firms. (Rockefeller received stock in all of them and became even wealthier.) In the decades following the Standard Oil breakup, antitrust enforcement generally abided by a core principle: When a company grows so powerful that it becomes a gatekeeper, and uses that might to undermine competitors, then the government should intervene. And in the last century, as courts have censured other monopolies, academics and jurists have noticed a pattern: Monopolies and technology often seem intertwined. When a company discovers a technological advantage — like the innovations of Rockefeller’s scientists — it sometimes makes that firm so powerful that it becomes a monopoly almost without trying very hard. Many of the most important antitrust lawsuits in American history — against IBM, Alcoa, Kodak and others — were rooted in claims that one company had made technological discoveries that allowed it to outpace competitors.

For decades, there seemed to be a consensus among policymakers and business leaders (though not always among targeted companies) about how the antitrust laws should be enforced. But around the turn of this century, a number of tech companies emerged that caused some people to question whether the antitrust formula made sense anymore. Firms like Google and Facebook have become increasingly useful as they have grown bigger and bigger — a characteristic known as network effects. What’s more, some have argued that the online world is so fast-moving that no antitrust lawsuit can keep pace. Nowadays even the biggest titan can be defeated by a tiny start-up, as long as the newcomer has better ideas or faster tech. Antitrust laws, digital executives said, aren’t needed anymore.

Consider Microsoft. The government spent most of the 1990s suing Microsoft for antitrust violations, a prosecution that many now view as a complete waste of time and money. When Microsoft’s chief executive, Bill Gates, signed a consent decree to resolve one of its monopoly investigations in 1994, he told a reporter that it was essentially pointless for the company’s various divisions: “None of the people who run those divisions are going to change what they do or think.” Even after a federal judge ordered Microsoft broken into separate companies in 2000, the punishment didn’t take. Microsoft fought the ruling and won on appeal. The government then offered a settlement so feeble that nine states begged the court to reject the proposal. It was approved.

What eventually humbled Bill Gates and ended Microsoft’s monopoly wasn’t antitrust prosecutions, observers say, but a more nimble start-up named Google, a search engine designed by two Stanford Ph.D. dropouts that outperformed Microsoft’s own forays into search (first MSN Search and now Bing). Then those two dropouts introduced a series of applications, like Google Docs and Google Sheets, that eventually began to compete with almost every aspect of Microsoft’s businesses. And Google did all that not by relying on government prosecutors but by being smarter. You don’t need antitrust in the digital marketplace, critics argue. “When our products don’t work or we make mistakes, it’s easy for users to go elsewhere because our competition is only a click away,” Google’s co-founder, Larry Page, said in 2012. Translation: The government ought to stop worrying, because no online giant will ever survive any longer than it deserves to.