Justin Trudeau landed in the Philippines on Sunday with the goal of raising Canada's profile in the Asia-Pacific region, especially on security issues and trade.
This week, Trudeau will become the first sitting Canadian prime minister to participate in the annual East Asia Summit and is the only one who's ever been invited, his office said.
Foreign Affairs Minister Chrystia Freeland said that the East Asia Summit will give Trudeau a chair at the top security table in the region.
He will sit alongside Chinese President Xi Jinping and U.S. President Donald Trump during discussions on the security situation involving North Korea, she said.
"That is a really big deal," Freeland said of the forum, which is held in conjunction with the annual summit of the Association of Southeast Asian Nations.
"Canada has never been there before."
The ASEAN summit itself will give Trudeau an opportunity to raise concerns about human rights and advance his trade agenda with the emerging bloc of 10 Southeast Asian countries, which is already Canada's sixth-largest trading partner.
Combined, the countries boast a market of 640 million people and an expanding middle class. They have been churning out significant economic growth.
With the uncertainty surrounding Canada's NAFTA renegotiation, the Asia-Pacific has become increasingly important in the government's eyes.
Under Liberal and Conservative governments, Ottawa has taken steps in recent years to increase its presence in the region.
Canada named its first ambassador dedicated to ASEAN in 2014. In September, the government opened exploratory free-trade talks with the association.
"We are very much positioning ourselves in the Asia-Pacific," International Trade Minister Francois-Philippe Champagne said in an interview before Trudeau left for his week-long trip to the region.
Experts, however, say Ottawa has largely failed in the past to maintain a consistent connection with ASEAN members.
David Mulroney, a former Canadian ambassador to China, believes forging closer relations with ASEAN should be Ottawa's second-most important priority in the region after Beijing.
Canada, however, has struggled to maintain a disciplined focus on the region and hasn't been as plugged in with ASEAN as Australia or even the United States, Mulroney added.
"When we're at our best, we are a very popular partner in ASEAN," said Mulroney, who noted that members of the group still recall a time when Canada was more deeply engaged with them, decades ago.
"We haven't given them reason to believe that it's anything other than nostalgia, but I think Canada could be a very capable player in the region."
He said ASEAN maintains tighter dialogue partnerships with other countries outside the region, like Russia, the U.S. and Australia.
"We have yet to kind of crack that inner circle, in part because there are doubts about our commitment and our staying power," Mulroney said.
Former Quebec premier Jean Charest, now the honorary chair of the Canada-ASEAN Business Council, said in a recent interview that Trump's protectionist story makes the case every day on the importance of diversifying.
Compared to China, Charest said ASEAN is a less-complex partner to work with.
"Canadians will have more reservations about China, which doesn't mean that we should not pursue an initiative with China, but it's just politically more complicated," he said.
In moving closer to ASEAN, Ottawa would still have to navigate the delicate issue of human rights — particularly amid concerns about serious, state-led violence by two of its members: Myanmar and the Philippines.
On Saturday, Trudeau was asked whether he intended to challenge Philippine President Rodrigo Duterte about the deadly, anti-drug crackdown by security forces in his country. The campaign has killed thousands of suspects, most of whom are poor.
Trudeau has said he has no one-on-one meeting planned with Duterte, who will host the ASEAN summit.
"There are a range of issues that I could bring up with him, that I may bring up with him, if we have an opportunity," Trudeau told reporters Saturday in Danang, Vietnam.
"There's always human rights concerns to bring up with a wide range of leaders."
On Sunday, Freeland said Canada has "some serious concerns about human rights violations and violations of due process in the Philippines."
"If we get the opportunity, we will talk about these issues," said Freeland, who added that she raised them in a meeting last summer with the Philippines' deputy minister of foreign affairs.
David Welch, CIGI chair of global security at the Balsillie School of International Affairs, said ASEAN countries likely wouldn't appreciate Canada pressuring them on these issues, which could put Trudeau in an awkward position as he tries to deepen the relationship.
"They don't want us to talk about human rights," Welch said.
The ASEAN bloc includes the Philippines, Indonesia, Brunei, Singapore, Malaysia, Thailand, Vietnam, Laos, Cambodia and Myanmar.
Trudeau's visit to Manila is the last stop in his week-long trip to the region, which included an official bilateral visit with Vietnam and the APEC leaders' summit.
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