White House officials hope the first meeting on U.S. soil between the United States and the Association of Southeast Asian Nations, or ASEAN, will provide another legacy-boosting step for Obama, who has sought to foster ties with the group as a way to counter an increasingly assertive China.
He welcomes the leaders Monday afternoon to Sunnylands, the secluded midcentury estate outside Palm Springs, California. The setting is symbolic: Obama hosted Chinese President Xi Jinping at the site in 2013, his first formal session with the newly installed Premier.
Three years after that "shirtsleeves summit" -- so-called because temperatures in the Coachella Valley rose to triple digits during Xi's visit -- Obama welcomes some of China's antagonistic neighbors, riled in disputes with the continental powerhouse that they believe only the United States can help mitigate.
Like much of his schedule these days, Obama's trip to Rancho Mirage also looks to bolster a long-running aspect of his legacy agenda: rebalancing the country's foreign policy eastward toward Asia.
It comes as the rest of the world begins to look beyond Obama to his potential successors and assess the next administration's foreign policy.
"Everybody in the region is watching American politics. It's better than the Super Bowl. Better than Beyonce," said Patrick Cronin, senior director for the Asia-Pacific Security Program at the Center for a New American Security.
"They're very worried about a downturn in U.S.-Southeast Asian relations -- sure," he continued. "But that's all the more reason to get as much out of the current administration as you can."
That includes seeing final approval of Obama's Trans-Pacific Partnership trade deal, a major pillar of Obama's presidential legacy. The Republican-led Congress has avoided action to ratify the pact and both Democratic presidential candidates have disapproved of it.
Obama hopes to drive home the benefits of the deal during this week's summit, pointing to new labor regulations the deal would spur in countries like Vietnam, where conditions for workers are poor.
Administration aides have long cited the importance of "showing up" in managing relations with Asian nations, scheduling presidential trips to the continent every year of Obama's tenure in a public show of commitment to the region.
Even as foreign policy challenges persisted in the Middle East, Obama's aides stressed the importance of the leaders' summits that form the backbone of U.S. ties to Asia.
"This will kick off, I think, a year of significant attention on the Asia-Pacific," said Ben Rhodes, Obama's deputy national security adviser, citing scheduled trips to Japan, China and Laos.
"By bringing all of these leaders here to the United States, to Sunnylands, we could both finalize what we want to get done in this last year in office, but also send the message going forward that we do believe there should be this level of engagement with Southeast Asia," he said.
Like many U.S. engagements around the globe, the relationships in Southeast Asia have sometimes proven troublesome for Obama; autocratic rulers attending this week's gathering include Thailand's military chief, who led a junta to power in 2014, and Cambodia's Prime Minister Hun Sen, whose rule most view as a dictatorship.
Even relationships that once seemed noncontroversial now appear questionable. Malaysian Prime Minister Najib Razak, with whom Obama played a round of golf in Hawaii last year, is accused of embezzling more than half-a-billion dollars from his country.
But U.S. officials say engagement, especially on efforts to combat terrorism, outstrips any potential benefits in cutting off relations.
A major terrorist attack in Indonesia last month underscored the threat ISIS and related groups pose in Southeast Asia, even as the focus remains on the fight in the Middle East.
Obama this week hopes to persuade leaders from affected nations -- many of which have large but moderate Muslim populations -- to cooperate with international law enforcement efforts to better track and prevent terrorist attacks and to more closely monitor potential ISIS recruits.
Cronin said even though some U.S. partners on the issue might be tainted, they were important to work with. He pointed to the corruption scandal around the Malaysian President, saying, "He's wounded politically over corruption charges. We wish it were otherwise. But he's an extremely important voice on dealing with stopping radicalization."
Cronin continued, "There's a rise of terror and radicalization. There's a growing essential highway of trafficking going on of people and weapons and money from ISIS-controlled areas throughout parts of Southeast Asia. And this is something that has to be stopped."