President Donald Trump has trade at the top of his Group of 20 agenda, yet key issues including Iran, North Korea and next year’s presidential election will vie for his attention and create opportunities for summit pitfalls.

In addition to a meeting with his Chinese counterpart that will be the centerpiece of his trip to Japan this week, Trump will also meet with the leaders of Russia and Turkey — two men who have outmaneuvered him in the past. The summit will unfold on Friday and Saturday as tensions between the U.S. and Iran continue to escalate.

Before returning to Washington, Trump will visit South Korea, a trip marked by intrigue over whether he’ll visit the Demilitarized Zone marking the border with North Korea. He’ll also have to navigate extensive news coverage of the two nights of debates featuring the Democrats seeking to deny him another term.

Together, the events present a series of opportunities for Trump to advance American priorities and perhaps his own re-election interests. But they also carry risk, as Trump has demonstrated he’s just as likely to wind up with little to show for his effort but damaged international relations and embarrassing missteps.

The U.S. president touches down in Osaka on Thursday, the same day that Iran has said it would breach the cap on its enriched-uranium stockpile, a major test of the 2015 nuclear deal. Trump on Monday signed an executive order imposing new sanctions on Iran’s supreme leader, Ayatollah Ali Khamenei, and eight senior military commanders.

He plans to meet with Russian President Vladimir Putin, even after scratching an official meeting at last November’s G-20 to punish the Kremlin for a naval clash in the Black Sea in which Russia forces captured 22 Ukrainian sailors. The sailors have yet to be returned.

Putin and Trump are expected to focus on regional security, arms control and improving relations between the two countries, a U.S. official said. The two leaders are expected to discuss Iran and Syria.

Trump’s last extended encounter with Putin was last July in Helsinki, where the two leaders held a news conference at which the president sided with the Russian leader in questioning U.S. intelligence officials’ conclusion that the Kremlin interfered in the 2016 election. Trump was castigated by lawmakers in both parties back home.

He’ll also meet in Osaka with Turkish President Recep Tayyip Erdogan, with whom Trump maintains warm relations despite Erdogan’s turn toward autocracy and increasing friction between their governments. The U.S. is preparing sanctions on Turkey if it goes ahead with the purchase of a Russian anti-aircraft missile system.

In December, Trump issued a snap order to withdraw American military forces from Syria after a phone conversation with Erdogan in which the Turkish leader apparently talked him into the decision.

But Trump’s highest profile meeting will focus on a growing trade dispute with China. He likely to talk to China’s Xi Jinping on Saturday, the final day of the two-day summit, according to a U.S. official. They may agree to reopen trade talks, though no deal is expected from the summit, according to a senior administration official.

The U.S. is willing to suspend the next round of tariffs threatened by Trump on an additional $300 billion of Chinese imports while Beijing and Washington prepare to resume negotiations, people familiar with the plans said. A decision, which is still under consideration, could be announced after Trump and Xi meet.

Trade negotiations broke off last month after the U.S. accused China’s leaders of reneging on provisions of a tentative agreement, and Beijing said the U.S. had raised its demands. Trump raised tariffs on about $200 billion of Chinese imports to 25%, and said he would expand the tariffs to cover essentially everything China exports to the U.S. unless the country’s leaders reversed course.

The U.S. aggravated the trade dispute by targeting a Chinese telecommunications company, Huawei Technologies Co., and now China is examining a similar move against a U.S. shipping company, FedEx Corp. The U.S. blacklisted Huawei, saying it poses a national security threat. China is considering adding Memphis-based FedEx to a blacklist of firms that the government says damage the interests of domestic companies, people familiar with the matter said.

Michael Green, the Japan chair at the Center for Strategic and International Studies and a former National Security Council aide to President George W. Bush, said the typical strategy heading into a meeting with a leader like Xi is to first rally with allies at a summit such as the G-20.

“You build as much momentum as you can so that when you have your bilateral summit with Xi Jinping you’re speaking with the rest of the world kind of behind you,” Green said. But “we’re not doing that,” under Trump, Green said. “What we’re doing is we’re saying loudly that, we’re the sheriff, and there’s a bad guy at the end of the street, and we’re going to get him, and we’re calling a posse together which will be Japan and Europe, and then we’re shooting at them” by threatening auto tariffs.

“The president will go into this summit with Xi Jinping alone. Alone. And it’s not an enviable position.”

Trump’s travel also overlaps with the first set of Democratic presidential debates back in the U.S. The event, featuring 20 of the Democratic hopefuls over two nights, is likely to be heavy on criticism of the president and threatens to take away the spotlight from his activities, unless he can use the G-20 stage – and Twitter – to wrest control of the story. The president has mused about the possibility he would live-tweet his debate impressions from abroad.

As Trump prepared to leave for the G-20, his son-in-law Jared Kushner and Treasury Secretary Steve Mnuchin were leading a U.S. delegation to Bahrain to try to build support among Persian Gulf nations for a $50 billion economic plan to entice Palestinians to agree to a political peace plan with Israel. And Trump’s national security adviser, John Bolton, an Iran hawk, traveled to Israel for a summit with Russian and Israeli national security officials to discuss Iran’s reach in Syria.

Trump also plans to meet with Saudi Arabia’s Crown Prince Mohammed bin Salman about regional stability, a U.S. official said. The talks will come less than a week after the Senate voted to block arms sales to the kingdom. Republicans and Democrats have demanded greater scrutiny of Saudi Arabia over the military campaign it’s leading in Yemen’s civil war and over the killing of Washington Post columnist Jamal Khashoggi last fall.

Trump is also expected to meet other world leaders at the summit, including: Chancellor Angela Merkel of Germany; Prime Minister Shinzo Abe of Japan; Prime Minister Scott Morrison of Australia; and Prime Minister Narendra Modi of India.

After the G-20, Trump is set to meet in Seoul with South Korea’s President Moon Jae-in. Trump and Moon have no plans for a trilateral summit with North Korean leader Kim Jong Un, according to an official from South Korea’s presidential office.

Yet the visit may shape Trump’s thinking on how to pursue a third summit with Kim. They met in Singapore in 2018 and in Hanoi earlier this year but have yet to make substantive progress on dismantling North Korea’s nuclear program. Still, the two have continued to exchange letters – most recently, Trump said Kim sent him good wishes when for his birthday, when he turned 73 on June 14.

Bloomberg’s Jihye Lee, Nick Wadhams, Ivan Levingston and Henry Meyer contributed.