WASHINGTON - Promised talks this month between the United States and North Korea will give President Donald Trump yet another chance to conclude a deal with the reclusive nation, something that has eluded several of his predecessors.
But after three summits and more than two years of on-and-off talks, some analysts are asking just how well Trump's self-proclaimed prowess as a dealmaker translates to the world of diplomacy.
This week, Pyongyang said it is willing to meet with Washington later in September through a message conveyed in its state media Korea Central News Agency (KCNA).
"I think the record is beginning to become clear that he is not as great a dealmaker as he believes and as he has advertised," said Alexander Vershbow, who served as an ambassador to South Korea during the George W. Bush administration.
Trump has presented himself as a master dealmaker who can transfer his business dealmaking skills into the world of politics and diplomacy since announcing his candidacy in 2015.
"I make a good deal," Trump said as he prepared for his presidential bid for the White House in 2015.
"Deals are my art forms," said the author of "The Art of the Deal" in 2014. "I like making deals, preferably big deals. That's how I get my kicks."
Christopher Hill, a chief U.S. negotiator in nuclear talks with North Korea during the George W. Bush administration, said, "I'm skeptical that that type of business dealmaking can really translate into diplomatic so-called dealmaking."
Wendy Sherman, who served as North Korea policy coordinator during the administration of President Bill Clinton, said if Trump didn't get a deal in the real estate development market, he could seek another opportunity.
"But when it comes to war and peace, when it comes to the economic prosperity of the United States, things are little bit more complicated," Sherman said.
Baruch Fischhoff, a professor at Carnegie Mellon University's Institute for Politics and Strategy, said Trump's dealmaking with world leaders is influenced by his dealmaking in the business world.
"Mr. Trump's business experience is primarily as a real estate developer," Fischhoff said. "In that business arena, it was possible for him to have major properties go bankrupt and still get funding for new ones."
In the world of business, deals are often viewed through the lens of cost and benefit analysis, and strategies involved are aimed at maximizing profit while minimizing cost, said Vershbow, the former Bush administration ambassador.
However, in the world of diplomacy, Vershbow continued, costs and benefits cannot always be assessed in monetary terms and strategies involved cannot solely be based on gaining financial advantage.
"In the business world, you're talking about economic benefits and costs," he said. "It's kind of fairly dry but straightforward. In [diplomatic] negotiations, there're many different factors in terms of building trust between different countries, different cultures, and calculating the interest of third parties who may not directly be involved but could be affected. So it's more complex undertaking."
It is in the international system of alliances where Trump's business calculations tend to overshadow the building of relationships and fostering intrinsic values, said Bruce Klingner, former CIA deputy division chief of Korea and current senior research fellow at the Heritage Foundation.
"Trump's transactional views on the U.S. alliance and the stationing of American troops overseas are at odds with 70 years of post-World War II American strategy," Klingner said. "Seeking alliances as business transactions, rather than based on [sharing] common values and strategic objectives, is a disservice to the men and women in the U.S. military."
On the Korean Peninsula, Trump has been demanding that South Korea pay more to keep the U.S. troop presence there to guard against a North Korean threat. And while Seoul has agreed to pay more, it rejects Trump's view that it is not paying enough.
In pursuing a denuclearization deal with Pyongyang, Trump began dealing with the North Korean leader himself in a so-called top-down approach toward diplomacy. This had the two leaders beginning the talks rather than adhering to the diplomatic convention of using working-level negotiators to put together a deal before any top-level meeting.
Sherman said, "The president sort of left things at the top and keeps saying what a great relationship he and Kim have." She continued, "Personal relationships certainly matter. [But] in very complex negotiations, it is not nearly sufficient."
Trump boasted of a beautiful letter he received from Kim even as North Korea was firing missiles in August amid stalled talks, and Trump frequently said North Korea has "tremendous economic potential," in an apparent move to lure Pyongyang to the negotiating table.
"Trump started talking about beachfront condos as he did in Singapore," Hill said, mentioning the location of the first Trump-Kim summit in 2018. "Maybe he believes. I don't think the North Koreans do. I don't think anyone else does."
At the Hanoi summit, Trump walked away from making a deal after North Korea rejected the U.S. proposal to give up its entire nuclear weapons program and instead offered a partial denuclearization in exchange for sanctions relief.
Vershbow said a big-deal approach that demands a full denuclearization up front is ineffective because of the complications involved, including getting North Korea to inventory its nuclear arsenal, and verifying and inspecting its nuclear program.
"[Trump] thinks he can have a big bang and all the issues will fall into place," Vershbow said. "That's sometimes possible. But in the case of North Korea, clearly, there are ... tremendous complications .... so this is simply impossible to solve with a big bang. You need to accept certain incrementalism."
Vershbow continued that a big deal approach could be risky, putting the U.S. and its allies, South Korea and Japan, in "a corner."
"Once you say it's all or nothing, either you succeed or if you fail, you're sort of forced to escalate and possibly even bring in military threats rather than having more modest expectations and proceeding step-by-step and maybe creating some momentum," he said.
Vipin Narang, a professor of political science and a North Korea expert at the Massachusetts Institute of Technology, said Trump might "blame [the outgoing National Security Adviser John] Bolton for the Hanoi hold-up, and reset America's negotiating position toward a step-by-step deal, comprehensive in scope but implemented in phases."
Trump announced he fired Bolton on Tuesday over disagreements on foreign policy issues, including North Korea. Bolton was known for taking a tough stance on North Korea, and against Trump's overtures to Kim and their meeting at the inter-Korean border in June.