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Trump leaves behind a wake of indictments and criminal charges against his campaign officials and advisers, as part of Special Counsel Robert Mueller's investigation into Russia's 2016 election meddling, and a fight in Congress over his proposed tax cuts.
In Asia, Trump will address security and trade concerns in Japan, South Korea, China, Vietnam, and the Philippines.
Between the US, South Korea, and Japan, the North Korean missile threat looms large and Trump is expected to reaffirm the US's commitment to the countries' alliance, though he has in the past questioned if the Asian allies pay their fair shares.
With China, the emerging world power that Trump accused of currency manipulation and "killing us" with a trade deficit, the US appears to actually have made progress. China now cooperates with the US on containing and limiting trade with North Korea like never before.
China apparently dropped its opposition to the deployment of THAAD missile
Additionally, China's concessions come at a time where Trump has the US Navy routinely challenging Beijing's excessive maritime claims in the South China Sea, something that routinely angers China.
Importantly, Trump's visit to China comes as its president, Xi Jinping, consolidates power to a level never seen since Chairman Mao's decades-long rule. In Japan, Prime Minister Shinzo Abe just won an election and reaffirmed his mandate to rule the island nation as assertively as has been done since World War II.
Reuters/Carlos Barria
In the Philippines, Trump will meet the popular populist Rodrigo Duterte, who looks to wrap up a violent drug war that's killed thousand and crush an Islamist insurgency in Marawi.
Duterte has at times been hostile towards the US, and the Philippines, a US ally, can be seen as a bell-weather in the shifting power dynamic in Asia. In March of this year, Duterte lamented that despite US support, he couldn't do anything to stop China from building islands and militarizing the seas just outside of the Philippines.
"What do you want me to do? Declare war against China? I can't. We will lose all our military and policemen tomorrow and we (will be) a destroyed nation," Duterte said at the time. Trump may potentially try to reassure Duterte, whose country holds massive US military bases in the Pacific.
Art of the deal?
Kevin Lamarque/Reuters
On trade, Trump's accompanying business envoy will include mainly energy firms instead of tech or financial companies - possibly playing to a US strength, and possibly covering up a tech industry that's unenthusiastic about the current administration.
Tech companies face an uphill battle in China, where the US maintains that the government favors domestic firms and can force foreign tech firms to give up intellectual property only to find those trade secrets leaked to Chinese firms. On the finance side, some companies allege off the record that Beijing informs domestic banks of important banking decisions before foreign firms.
Trump's rocky relationship with US industry leaders may also contribute to the makeup of his business envoy, with an unnamed member of the business community telling Reuters, "very few want to stick their heads up and be perceived as complaining directly," about China's treatment of foreign companies, "and even fewer trust this White House to do anything helpful on their issues."
But the US remains competitive in energy prices and Trump's chief diplomat and former head of energy giant Exxon, Rex Tillerson, will accompany him on the trip.
Penning a deal to sell off some of the US's glut of natural gas to Asian partners could be a possible trade victory for Trump in Asia.
But with Trump a full 12 hours ahead of the US in China, and similarly removed from the US time zone, expect quieter days where Trump news comes after events take place, instead of as a live show.