Henry Nicholls / Reuters

It seems about as black-and-white a situation as an American president can face in this messy world of ours: hundreds of thousands of largely peaceful protesters—at points as much as a quarter of Hong Kong’s entire population—spilling into the streets of the former British colony to demand greater democracy and resist China’s creeping control over the semiautonomous region.

All the more so for this particular American president, who for nearly a decade has styled himself as the man who will finally stand up to China. Speaking to reporters on Wednesday, he looked toward the heavens and suggested he was put on this Earth to challenge Beijing’s economic dealings. “I am the chosen one,” he said. “Somebody had to do it. So I’m taking on China. I’m taking on China on trade.” His administration has identified the struggle between free societies and authoritarian powers like China as the “central challenge to U.S. prosperity and security.” This summer, that struggle has come right up to China’s southern coast, in the beating heart of Asia.

As a senior Trump-administration official, who, like some others contacted for this article, spoke on the condition of anonymity in order to candidly discuss the topic, told us this week, “Hong Kong is a bellwether for China’s ability and intention to color the world in a more authoritarian hue.”

Yet in the throes of this hugely consequential moment, Donald Trump, no stranger to sounding off on the issues of the day, has mostly been mute. At times he seemed to condemn the people in the streets clamoring for more self-government, suggesting the demonstrations amounted to a criminal act. At least one foreign diplomat told us he is confounded by the administration’s position, sifting through the various statements from Trump, National Security Adviser John Bolton, and Secretary of State Mike Pompeo hoping to find clarity. A nation that itself broke free from colonial control has, under Trump, struggled to come up with a clear, consistent position on a massive demonstration from people chafing at Chinese rule.

Trump has only become more vocal in recent days amid bouts of violence between protesters and police and an ominous buildup of Chinese security forces along the border with Hong Kong. (There’s already a Chinese military garrison in Hong Kong.) Even then, however, he’s spoken out with nowhere near the fervor he devotes to discussing Chinese trade practices or, for that matter, the size of the crowds showing up at his rallies.  

The seismic developments in Hong Kong mark another instance in which Trump has had to reckon with competing imperatives that may be irreconcilable: pursuing his trade agenda, and playing the American president’s traditional role of promoting democratic ideals.

Trump confronted a similar dilemma with Saudi Arabia. Rather than punish the Saudi leadership over the kingdom’s role in the murder of the journalist Jamal Khashoggi, Trump said that arms sales were ultimately too important to jeopardize relations with a rich ally.

What his approach to Hong Kong has laid bare is the extent to which Trump diverges from his predecessors in modern American history, who tended to instinctively embrace the forces of freedom, so central to America’s own founding, even if they often failed to make good on their lofty rhetoric in practice.

That’s not the way Trump is wired. What moves him personally is America’s economic growth, which he sees as a zero-sum proposition: measured by trade deficits, GDP, jobs numbers, and, perhaps most important, the stock market. In 1990, he gave an interview that revealed his thinking about clashes between authoritarian leaders and protest movements looking for democratic freedoms. His admiration was for the crackdown. China’s massacre of civilians in Tiananmen Square the previous year was “vicious,” he declared at the time, but it showed “the power of strength,” which the United States needed more of.

Since the demonstrations erupted in Hong Kong several months ago, Trump has put forward a muddled message about the most overt challenge to Chinese authority since Tiananmen Square. For a spell, he and advisers such as Commerce Secretary Wilbur Ross characterized the ferment in the territory as an internal Chinese matter and flirted with a pro-Beijing stance. Trump used the Chinese government’s preferred term of “riots,” and stated that China and Hong Kong would “have to deal with that themselves” and “don’t need advice.”

As the standoff grew graver in mid-August, the president described Hong Kongers’ quest for more political rights and better governance as a “problem” that China’s leader, Xi Jinping (a “good man in a ‘tough business’”), could “humanely solve.” He even proposed a way to solve it: for Xi to meet with the leaders of the protests, and “work it out in 15 minutes.”

On Sunday the president struck a substantially different tone. He warned that any violence against protesters by Chinese forces—“another Tiananmen Square,” as he put it—would undermine negotiations to resolve the escalating trade war between Washington and Beijing.

Still, the takeaway was more don’t kill them than long live democracy. He distanced himself a bit from concern about a Chinese crackdown. “I’m president,” he said, “but that’s a little beyond me because I think there’d be tremendous political sentiment not to do something” on a trade deal in the event the protests are crushed. He expressed “support [for] democracy,” but only after a reporter literally said the words for him: “Do you support the principles of the protestors—the pro-democracy movement?,” the journalist inquired. When he lingered on that movement, it was to marvel at the size of the crowds rather than the causes behind them: “Those are serious crowds—the Hong Kong crowds.”

The foreign diplomat interpreted Trump’s statements on Sunday as “the officials around him trying to get him back on script,” noting that the president’s tweets have “muddied the waters when it comes to figuring out what exactly is the U.S. position.”

The senior Trump-administration official offered a different reading of the president’s remarks. “These messages were a public, topmost amplification of things we’ve been telling the Chinese in private for many weeks now,” the official said. “We’ve been in regular contact with the Chinese about the fact that there would be consequences if China tried to use force and intervene directly in Hong Kong.”

Trump’s call for Xi to dispense with Communist Party convention and engage in direct dialogue with representatives of the demonstrators, the official added, is an inspired idea. Trump was, in effect, challenging Xi to take part in the sort of dialogue that happens routinely in democratic nations, the official suggested. Still, Trump’s plan is rife with obstacles: The protest movement in Hong Kong is largely leaderless, the disputes Trump claims could be sorted out in minutes have been brewing for decades, no Chinese leader has met with protesters since the “Butcher of Beijing” did so ahead of the Tiananmen crackdown 30 years ago, and Xi would probably view such a meeting as legitimizing protests he considers a threat. As Trump himself has acknowledged, “That’s not his deal, sitting down with people.”

The Chinese government, for its part, has reacted to Trump’s new bid to help end the crisis by hurling his prior statements back at him, with spokespeople questioning why the U.S. president would possibly proffer advice he said the parties didn’t need and suggest Xi meet with those whom Trump has recognized as rioters.

Steve Bannon, Trump’s former White House chief strategist and a prominent China hawk, maintains that the president has been “smart” to stay “above” the fray in Hong Kong and thus make it harder for the Chinese to try and discredit the demonstrations as a U.S.-orchestrated plot. “Xi has not made one comment on Hong Kong in the whole 12 weeks” of protests, he told us. “Donald Trump, through his Twitter feed, has put the international spotlight on where it should be: not on the streets of Hong Kong, but on Xi, and that Xi can resolve this.”

Voices in the Trump administration also caution that positioning the U.S. government squarely on the side of the demonstrators could backfire spectacularly, spurring the Chinese government to launch a violent strike aimed at forcing the demonstrators to disband.

A former Trump-administration official concurred that the dilemma for the president is that “the more vocal you are in favor of the opposition, the more you give the autocratic leadership the opportunity to cast it as an American-led protest.” And yet a number of the president’s current and former advisers, along with allies in Congress, recognize that the Hong Kong protests are a historic moment that no president should discount.

“Hong Kong is everything,” Bannon said. “As Berlin was to the Cold War, so Hong Kong is to the conflict we’re in with China. And we’re in a conflict.”

In an apparent jab at the Trump administration’s initial approach to the issue, Senator Marco Rubio told us that “Hong Kong is not China’s internal affair because Beijing promised the world it would protect Hong Kong’s autonomy” as part of its 1984 pact with Britain on transferring control of the territory. If the Chinese government “cannot honor a legally binding treaty,” he argued, then why should the United States “trust its word” on trade or “retain Hong Kong’s special status?” The Florida Republican has joined other U.S. lawmakers in threatening to revoke Hong Kong’s favored status as an economic partner under a 1992 U.S. law, and thereby eliminate a source of enrichment for mainland China, if the Chinese government quashes the protests.

Trump, too, has at times been outspoken on matters of democracy and human rights, perhaps most prominently in Venezuela. But a second former Trump-administration official told us that there’s actually a “deliberate” and “strategic” division of labor at play in the White House: Vice President Mike Pence tends to focus on delivering messages about liberty abroad, while Trump tends to focus on delivering messages about economic issues abroad. (Pence has been one of the administration’s foremost voices on these matters, but in recent days he has hewed to Trump’s talking points on Hong Kong. The vice president reportedly canceled a planned speech on Chinese human-rights abuses earlier this summer ahead of a meeting between Trump and Xi on trade.)

Pence “has been vocal on those issues his entire career, so he’s the obvious, natural delivery mechanism of that message for the administration,” whereas “Trump has a greater comfort in the economic message and knows that he has to navigate some pretty prickly waters with some pretty tough hombres that lead these different countries, whether it’s Kim Jong Un or Xi,” the former official said. With Trump attempting to personally connect with such leaders and Pence taking the lead on issues related to democracy and human rights, the president has “the buffer” necessary to cut economic deals with these countries, the ex-official explained.

Critics would likely counter that advancing America’s economic interests and championing its values don’t always have to be mutually exclusive, and that the natural point person for promoting freedom in the U.S. government is the president, traditionally also known as the leader of the free world. If nothing else, Trump’s delegation of that role to his vice president and others in the administration suggests that it’s not his top priority. (The strategy has yet to yield any blockbuster trade deal with China.)

Granted, when similar protests broke out in Hong Kong in 2014, Barack Obama also proceeded cautiously. Like Trump, he urged the parties to refrain from violence. Like Trump, he denied any U.S. involvement in the demonstrations, hesitating to take sides. Like Trump, he openly juggled American values and economic interests. As in Trump’s case, the president’s public utterances were only part of the story. “The Obama administration conducted the bulk of its communication privately,” for example pressing China’s foreign minister behind closed doors to maintain the territory’s open system, Ryan Hass, who oversaw China policy on Obama’s National Security Council, told us. (At the time, Trump urged Obama to “stay out of the Hong Kong protests” because “we have enough problems in our own country!”)

But there was one key distinction between then and now: the widespread assumption that the American president stood the same ground that his predecessors had for decades. So entrenched was this assumption that Joshua Wong, a young leader of the protests in Hong Kong, was disappointed when Obama merely endorsed the common human desire for the freedoms Americans hold dear and he and his fellow activists were seeking.

“Barack Obama’s administration gave obvious statements, as if they’re telling us, ‘Your mother is a woman,’” Wong told The Wall Street Journal. “Who wouldn’t know that they support Hong Kong’s democracy? Hong Kong needs more than a few words from Obama.”

Now, even that rhetorical support isn’t a given. “Under the current leadership of President Trump,” Wong told CNN earlier this month, “business interests or the daily life of Americans might be more important than human rights.”

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