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From Nov. 5 to Nov. 14, the 71-year-old leader will stop in Japan, South Korea, China, Vietnam and the Philippines in his first visit to the region since taking office. It's the longest trip to Asia by any sitting U.S. president this millennium.
In addition to state visits with each nation's respective leaders, Trump will also be attending the Asia-Pacific Economic Cooperation, or APEC, forum and the U.S.-ASEAN Summit. Headlining his overall agenda will be the creation of a united front against Pyongyang's nuclear threats as well as reassuring regional leaders of America's defensive capabilities and trade cooperation.
Trump's foreign policy agenda is rooted in his 'America First' program, explained Anne-Marie Slaughter, a former director of policy planning at the U.S. State Department who's now president and CEO of think tank New America.
As a result, he's expected to be assertive and pushy in demanding the best deals and concessions Washington can get in Asia, Slaughter told CNBC on the sidelines of the Barclays Asia Forum on Thursday.
"But the question is how well that works with the diplomacy he needs to engage in Beijing, Korea and Japan around subjects like North Korea," she warned.
For Asian governments, the visit is a chance to address longstanding doubts over America's interest in the region.
Trump's actions, which include withdrawing the U.S. from the Trans-Pacific Partnership agreement and talking up trade deficits, have weakened American credibility and "shaken allies' belief in U.S. staying power," David B. Shear, former assistant secretary of defense for Asian and Pacific security affairs, wrote in a recent note.
An ongoing FBI investigation into Trump's associates could also hurt the president's image among Asian head of states.
Trump "is not a strong president at the moment," said Slaughter. That's in contrast to Japanese Prime Minister Shinzo Abe and Chinese President Xi Jinping, who recently secured strong political mandates at home: Abe's party won recent parliamentary elections while Xi was enshrined in China's Communist Party constitution. Trump "has had a cloud of scandals so I do think other leaders will factor that in and recognize that he's not in a strong political position that allows him to impose terms," Slaughter noted.
Amid those concerns, here's what to expect from the president's milestone Asia tour.
Trump will arrive in Tokyo on Nov. 5 for a two-day stay. In addition to bilateral talks with Abe and a potential round of golf, Trump is due to meet families of Japanese citizens abducted by the North Korean regime.
The latter event will soften Trump's image in Japan and simultaneously bolster Abe's position as a leader who can talk to Washington on issues important to Japanese citizens, according to Stephen Nagy, associate professor at Tokyo- based International Christian University.
Discussions on joint cooperation in the Indo-Pacific region to balance China's military footprint may also be on tap.
Nagy expects a strong statement on Washington's commitment to defending Japanese territories, including an East China Sea island cluster that's claimed by both Tokyo and Beijing. That will send "an explicit message" to Xi, Nagy said.
Abe, who wants the U.S. to return to the TPP deal, isn't expected to bring up the pact for fear of ruining his carefully cultivated relationship with Trump, but the U.S. leader will likely push for a bilateral free trade deal, according to Nagy.
On Nov. 7, Trump meets South Korean President Moon Jae-in and North Korea is likely dominate the one-day visit. The two leaders espouse varied views on reigning in the rogue state, but both are expected to stay united on issues such as joint defense networks.
In addition to a state dinner, Trump will also visit Camp Humphreys, home to one of the U.S. army's busiest overseas airfields, and a national cemetery.
Ties between Washington and Beijing remain complex: The White House regularly criticizes Xi's government on market access and aggressive behavior in the South China Sea but still asks Beijing for help on containing Pyongyang.
Both leaders have different objectives for the Nov. 8-10 visit, Ryan Hass, a foreign policy expert at think tank the Brookings Institution, said in a recent note.
"Xi's goal will be for Trump to leave Beijing satisfied that he was accorded due respect and convinced that he should continue pursuing a constructive, results-based approach to China in order to achieve the goals he seeks — more balanced trade and better cooperation on North Korea."
The U.S. leader, meanwhile, will seek to convince Xi that Beijing must moderate its behavior to preserve against imbalances in the bilateral relationship, especially when it comes to the treatment of U.S. firms in China.
"Unlike previous state visits where deliverables were negotiated for months and used as yardsticks of the success of the visit, Trump would like the lasting legacy of this summit to be his success in compelling Xi to adopt an attitudinal shift in his approach to the relationship," Hass said.
On Nov. 10, Trump arrives in the Vietnamese city of Da Nang for the APEC summit, where he'll deliver a speech and potentially meet Russian President Vladimir Putin on the sidelines.
A day later, Trump will meet with senior Vietnamese leaders in Hanoi, including Prime Minister Nguyen Xuan Phuc. Vietnam is Southeast Asia's largest exporter to the U.S. and talks will likely focus on expanded trade opportunities.
Critics, however, have lashed out at Washington for visiting a country with a serious human rights record.
In Manila on Nov. 12, Trump will participate in a gala dinner for the 50th anniversary of the Association of Southeast Asian Nations, or ASEAN.
The next day, Trump will attend the U.S.-ASEAN summit and hold talks with President Rodrigo Duterte. That's also attracted international backlash given Duterte's controversial drug war, which has killed thousands. But the White House has defended Trump's visit, saying Duterte's cooperation is needed to counter North Korea.