But recent strides in Pyongyang's quest to develop a nuclear weapon capable of hitting the US have raised suggestions that the idea of engaging in direct diplomacy with the Kim regime -- or even facilitating a direct meeting between Trump and the North Korean leader -- might not be so crazy after all.
Trump currently finds himself at a critical juncture when it comes to identifying an effective diplomatic policy on North Korea.
After months of escalating tensions driven by harsh rhetoric and military muscle flexing, Pyongyang launched two intercontinental ballistic missile tests in July -- indicating that its missile program may be more advanced than previously thought despite years of sanctions levied by the international community.
The US and its allies in the region have overwhelmingly condemned both tests, with the White House repeatedly telling reporters that it is considering "all options" following the most recent launch that occurred just last week.
However, the White House has yet to offer a clear explanation of how the US intends to proceed -- despite intelligence assessments indicating that North Korea could have a reliable ICBM capable of reaching the US by 2018.
"The President obviously has been very outspoken about how he feels about North Korea. As we have said many times, we are not going to broadcast what we are going to do," White House press secretary Sarah Huckabee Sanders said Tuesday.
The Trump administration policy on North Korea to date has been to ratchet up the pressure on Pyongyang with sanctions in order to push them to the negotiating table.
But some analysts have said that advancements in Pyongyang's missile program showing they are able to launch an ICBM today are a game-changer.
"North Korea has crossed that critical threshold where it has ICBM capability. Time has run out here. There is no more waiting or wiggle room that we have," according to Adam Mount, a senior fellow at the Center for American Progress.
"From here on out they (North Korea) face a series of choices about how quickly they want to develop," he told CNN.
US officials told CNN last month that revised military options for North Korea have been prepared and were ready to be presented to President Donald Trump.
When asked about the US government's strategy on handling North Korea, GOP Sen. Lindsey Graham suggested Tuesday military options could be used to halt threats from the country.
"There is a military option to destroy North Korea's (missile) program and North Korea itself," Graham said on NBC's "Today" show. "If there's going to be a war to stop them, it will be over there. If thousands die, they're going to die over there, they're not going to die here and (President Donald Trump) told me that to my face."
He continued: "I'm saying (military options are) inevitable if North Korea continues."
But with millions of innocent people -- and nearly 30,000 US soldiers -- in South Korea and in range of Pyongyang's current missile arsenal, the administration is indicating that it still hopes to find a diplomatic resolution despite failed attempts to persuade China to take a more assertive role pressuring North Korea into talks.
"Talks stand the best chance of limiting North Korea's missile program, but it is still a slim chance," according to Mount, who added that logically and practically there is no other step for the US.
Several US lawmakers have publicly supported the idea of engaging in diplomacy with North Korea -- with some indicating a willingness to support direct talks with Pyongyang.
"If the choice is between military conflict or talking I would support talking," Democratic Rep. Ted Lieu told CNN when asked if he supports direct diplomatic engagement with the North Korean regime.
Democratic Rep. Martin Heinrich echoed the need for diplomacy but said the US should not give up on engaging China on the issue.
"I think having an open dialogue with North Korea, especially if the right messengers are at the table -- and that may not be the United States -- is not a bad thing and is something that should be explored," he said. "We probably need to be working in concert with countries who recognize just how much inherent risk there is in this situation. Even though China is often our adversary on issues we should be deeply engaged with China in trying to bring that to bear on North Korea," said Heinrich.
Trump has often stressed that China should do more to pressure North Korea into abandoning its missile program but he has made little progress toward persuading Beijing to take on a bigger role.
Without China's cooperation, the US may have to engage North Korea on its own.
US lawmakers and even members of the Trump administration have previously criticized the idea of engaging in direct talks with North Korea without the precondition of denuclearization.
In March, Secretary of State Rex Tillerson ruled out negotiations with North Korea, saying talks "can only be achieved by denuclearizing, giving up their weapons of mass destruction."
Tillerson took a softer tone in comments Tuesday, indicating that the US appears willing to move forward with direct talks if North Korea agrees upfront to pursue denuclearization -- a policy that was unsuccessfully implemented by the Obama administration and considered by some experts to be out-of-date.
By all indications, upfront denuclearization remains a non-starter for North Korea and by adopting that precondition for negotiations, the Trump administration sends a message that they are not serious about talks, according to Mount.
"The important thing to do is for the Trump administration to abandon its search for easy solutions," he told CNN. "The insistence of denuclearization -- which won't occur -- will likely not lead to any progress and will result in policy that is likely to be more destabilizing," he said.
Instead, the US could frame its policy around trying to contain North Korea by proposing an arms control agreement rather than demanding denuclearization.
"It costs the US nothing to make a sincere offer and leave it on the table to see if pressure on North Korea could lead to negotiations and expand from there -- from a modest beginning to more serious restrictions," Mount said.
While there is certainly no guarantee that direct negotiations would prove to be effective, experts indicate that there is a desire to come to the table on the part of the North Korean regime.
"The North Koreans have been wanting direct talks with the US for over a year but don't want to commit in advance to denuclearization or to take steps unilaterally before talks begin," said Leon Sigal, Director of the Northeast Asia Cooperative Security Project at the Social Science Research Council.
According to Sigal, North Korea's desire to change its relationship with the US dates back more than 30 years, and their hopes of altering US policy they see as adversarial could provide leverage in attempts to bring Pyongyang to the table.
But the years of mistrust continue to foster skepticism as neither side has shown a willingness to concede ground.
How would US allies react?
Engaging in direct talks with North Korea could anger several key allies in the region -- particularly if the US makes concessions in its military posturing.
Any idea that Washington might give ground on the US' ability to strike hard against North Korea's nuclear and missile programs would raise alarms in Tokyo, said Corey Wallace, a Japan security analyst at Freie University in Berlin.
"If there is any sense that the US might weaken its military position and ability to deliver this response as part of some deal, this will be seen with great concern in Japan," Wallace said.
Japan is home to several large US military bases. And without the ability to undertake offensive military operations on its own, Japan would need the US to retaliate against any North Korean aggression against it.
Tokyo is in no mood to make any concessions to Pyongyang, Wallace said.
"There is no longer a constituency in Japan advocating an engagement approach with DPRK like in South Korea. I don't think anyone will be second guessing a tough approach," he said.
However, new South Korean President Moon Jae-in has expressed a desire to initiate talks with his neighbor to the north in hopes of bringing about denuclearization on the Korean Peninsula through dialogue and cooperation. But efforts to create a dialogue have been unsuccessful to date.
Moon, who was inaugurated in May, campaigned on a platform of engagement, in stark contrast to his hawkish predecessor, though pre-election opinion polls showed security was not the top issue for the electorate.
A Trump and Kim face-to-face meeting?
No sitting US president has ever met with the leader of North Korea while in power, but in May, Trump said he would be willing to meet with Kim "under the right circumstances"
to defuse tensions over North Korea's nuclear program.
"If it would be appropriate for me to meet with him, I would absolutely, I would be honored to do it," Trump told Bloomberg News in an interview at the time. "If it's under the, again, under the right circumstances. But I would do that."
Trump's comments were later downplayed by then-press secretary Sean Spicer who said the conditions for a meeting "do not exist now" and that they may "never be there."
Ri Jong Ho, a North Korean defector who formerly worked for the government, says he believes a Trump-Kim meeting is a possibility.
"Even though they don't say so publicly, I believe they are anxious, they are afraid, and under tremendous international pressure," Ho said, referring to the North Koreans. "So even if they can't say so publicly they may want to have these talks. So I believe there is quite a possibility that the two of them could meet and talk."
The White House did not respond to CNN's request for comment on whether Trump would still be willing to meet with the North Korean dictator, but his comments date back to the campaign.
During a 2016 rally in Atlanta, Trump told the crowd he believed the criticism he's received on his willingness to talk to foreign leaders was unfair.
"I said absolutely, why not? Why not? And they came out: 'Trump would speak to him.' Who the hell cares? I'll speak to anybody. Who knows? There's a 10% or 20% chance that I can talk him out of those damn nukes 'cause who the hell wants him to have nukes, and there's a chance! I'm only going to make a good deal for us but there's a chance!" Trump said.
But the idea of Trump directly engaging Kim would break dramatically with the policies of several past administrations.
"North Korea unsuccessfully asked to meet with Bill Clinton repeatedly, also with George W. Bush and also with Obama," Sigal said, adding that North Korea would regard a meeting with Trump as "legitimating their standing in the world."
"I wouldn't want to give it away cheaply," he added, noting that the prospect of a meeting with Trump could potentially be used down the line in an effort to negotiate the forfeiture of key North Korean programs.
Adam Mount echoed Sigal's assessment that a face-to-face meeting should be reserved until progress was made on other issues.
"Trump has said he's willing to consider a meeting -- hold that out as a possibility contingent on other concessions like arms control measures," he said.