The four-day trip beginning Saturday will be the president's fourth to Asia. It comes amid unusual challenges at home, including opening discussions with lawmakers about dealing with the nation's fiscal health and a sex scandal that's roiling his national security team.
Still, Obama is eager to return to foreign policy matters that were put on the back burner by the campaign. The unprecedented visit to Myanmar, also known as Burma, gives the trip a historic edge while shoring up a strategic regional goal sought with stops in Thailand and in Cambodia, where he will attend the East Asia Summit in Phnom Penh.
The Asia trip underscores Obama's efforts to establish the United States as an Asia-Pacific power, a worldview defined by 21st century geopolitics but also by Obama's personal identity as America's first Pacific president. Obama was born in Hawaii.
"Continuing to fill in our pivot to Asia will be a critical part of this president's second term and ultimately his foreign policy legacy," deputy national security adviser Ben Rhodes said ahead of the trip.
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But Obama also heads out at a sensitive time for the U.S. economy. Only six weeks remain before automatic tax increases and deep spending cuts kick in—they create the so-called fiscal cliff—that could set back the economy if Obama and congressional Republicans don't find agreement on a deficit-reduction plan.
Stephen Hadley, national security adviser to President George W. Bush, cautioned that failure by Washington to resolve the fiscal cliff could signal to emerging economies that the democratic system is flawed.
"That's why countries are flirting with this notion that maybe China has it right: state capitalism plus keeping your people in line," he recently told the World Affairs Councils of America. "That is very destructive."
But China also has problems with corruption and a sluggish economy.
"Burma is sending a powerful signal that people are rejecting the notion that an authoritarian model is the key to development," Rhodes said.
The precarious nature of the budget negotiations is not lost on Asian countries, and Obama will likely find himself on the sidelines offering reassurances to other leaders that the U.S. will not plunge over a fiscal cliff.
"Some, particularly allies, will worry about the impact on defense spending at a time when Chinese power is rising," said Michael Green, a former Asia adviser to Bush who now is a senior vice president at the Center for Strategic and International Studies, a foreign policy think tank.
Telegraphing Obama's response to that concern, White House national security adviser Tom Donilon conceded that "after a decade of war ... there will be reductions in the U.S. defense budget."
He added: "Guided by our new defense strategy, our defense spending program will continue to support our key priorities, including our presence and missions in Asia."
During the brief stop Monday in Myanmar, Obama will meet with opposition leader Aung San Suu Kyi and President Thein Sein and deliver an address in which he will call for continued political reforms in a country that had been internationally shunned for decades.
The East Asia Summit includes the 10-member Association of Southeast Asian Nations and eight other nations: the United States, China, Japan, South Korea, India, Russia, Australia and New Zealand.