The floor of the New York Stock Exchange one day in 1948Bettmann / Getty Images

In big, bold letters, the homepage of the U.S. Chamber of Commerce’s website describes the organization’s mission: “Standing up for American Enterprise.”

But the huge business federation—like its counterparts, the Business Roundtable and other major corporate lobbies—was conspicuously silent when Donald Trump launched a salvo of tweets earlier this week accusing Amazon of dodging taxes, bilking the U.S. Postal Service, and undermining Main Street retailers. The assault, which wasn’t Trump’s first on the company, sent Amazon’s stock tumbling and precipitated a broader decline in the stock market on Monday—particularly in technology stocks—before it rebounded on Tuesday.

Finally, the Chamber issued a statement late Tuesday afternoon in the name of Neil Bradley, its executive vice president and chief policy officer. “It’s inappropriate for government officials to use their position to attack an American company,” Bradley said. “The U.S. economy is the world’s most powerful because it embraces the free enterprise system and the rule of law, whereby policy matters are handled through recognized policy making processes.”

It’s not hard to imagine that the response from the Chamber and other business groups would have been far faster and far more furious if a Democratic president had mounted such a sustained attack on a single U.S. company. The cautious reaction to Trump’s offensive against Amazon—like the limp response to his earlier onslaughts on enterprises, from Merck & Co. to Nordstrom to the NFL—reflects the complex bargain that Trump has struck with the nation’s corporate leadership. And it’s a deal the president is using to try to bend business to his will.

On the one hand, Trump is giving the business community virtually everything it wants on many of its key policy priorities. His tax bill slashed corporate taxes. Federal agencies are systematically rolling back financial, consumer-protection, and environmental regulations. While Trump is pursuing some policies that many businesses oppose—particularly the moves to restrict immigration and raise trade barriers that are central to his insular nationalism—generally he has aligned with corporate preferences as unreservedly as any president since at least Ronald Reagan (if not Calvin Coolidge).

For business, though, the price for those wins is accepting a president committed to publicly stoning companies and individual corporate leaders who cross him. Trump’s message seems to be that businesses that play ball will be rewarded and those that don’t will be punished. That’s a political logic familiar in strong-man governments that run the spectrum from old urban machines like Richard Daley’s Chicago on one end to autocracies like Vladimir Putin’s Russia on the other.

Nancy Koehn, a historian at Harvard Business School, told me that other presidents who criticized business’s power, like Franklin and Theodore Roosevelt, generally didn’t target individual companies. When Trump assailed Amazon and its founder, Jeff Bezos, taking “the stock price down by publicly singling out a company and its leader… relentlessly, and without a specific public-policy purpose, there is no precedent for that,” she said.

As Koehn noted, the closest comparison is probably the spring 1962 confrontation between John F. Kennedy and Roger Blough, the chairman of U.S. Steel. Blough infuriated Kennedy by announcing he would raise steel prices more than was recommended by Washington’s informal wage-and-price guidelines at the time. That announcement came immediately after the administration had pressured the United Steelworkers union to accept a leaner-than-usual contract.

Kennedy responded with a fierce public counterattack—which included a Justice Department investigation into alleged price fixing and threats to shift Defense Department steel procurement to companies that hadn’t raised prices. Within days Blough capitulated, reversing the increase.

Kennedy’s hardball tactics would draw criticism now, and justifiably so. But what’s most relevant today is how much criticism Kennedy provoked at the time from the same conservative voices now muted on Trump’s strong-arming. After Kennedy tried to mend fences with a conciliatory speech at the U.S. Chamber, the group’s president pointedly declared, “We should remember that dictators in other lands usually come to power under accepted constitutional procedures.”

That’s a long way from the Chamber’s current messaging. Even after Tuesday’s statement, an article on the group’s homepage, bylined by longtime president Thomas Donohue, declares: “As Election Looms, Business Optimism Soars.”

Scott Reed, the organization’s chief political strategist, told me he agrees that Trump’s presidency has presented an unusually challenging set of circumstances to both the group and the broader business community, which support him on some issues (taxes, regulation) and oppose him on others (trade, immigration). I asked Reed if he was afraid Trump’s attacks on Amazon and Bezos—whose ownership of The Washington Post has drawn Trump’s ire—were meant to intimidate other CEOs from criticizing the president when they think he’s wrong.

“‘Fear’ may be too strong of a word, but it’s a serious concern,” Reed said. The Chamber is examining whether it needs to push back harder, he added: “We are reconsidering all this, because this is unchartered waters.”

Another leading business lobbyist in Washington, who asked not to be identified because his clients have interests before the administration, said companies initially worried most about provoking a social-media backlash by identifying too closely with the White House. But now many are equally concerned about provoking social-media attacks from Trump by distancing themselves from him too overtly. The lobbyist said that while businesses don’t yet fear retribution for fighting administration policy decisions in private meetings, Trump’s Twitter tirades have made CEOs more cautious about publicly opposing him.

Koehn, citing recent actions by Delta and Walmart that support critics of the National Rifle Association in the gun debate, is more optimistic. She said that while companies may have initially feared Trump’s wrath, business “leaders are standing up for what they think is really important and I no longer think that corporate America is … afraid of Donald Trump.”

As Trump inevitably trains his sights on the next companies and executives he considers a threat, one way to measure which assessment is right may be to watch the headlines on the U.S. Chamber of Commerce’s homepage.

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