From threatening to destoy each other’s country’s, to a historic meet-and-greet, the relationship between U.S. President Donald Trump and North Korean leader, Kim Jong Un, has been one filled with fluctuations.
Nearly one year ago, Trump referred to Kim as “little rocket man.” And in retaliation, Kim threatened to send missiles at the U.S. territory of Guam, and called Trump a “mentally deranged U.S. dotard.”
READ MORE: Here’s what to expect from Trump-Kim summit in Singapore
But the emotional rollercoaster seems to have to come to a stop (at least for now) as the two leaders meet for a historic summit in Singapore on Tuesday morning.
Here’s a look at at the key moments of the rocky relationship between the two leaders over the past year.
WATCH: Trump arrives at Singapore hotel ahead of summit with North Korea
January 2017: Kim boasts about missile, Trump calls bluff
Kim declared that North Korea entered the final stages of preparation for a test of a nuclear missile that could reach the U.S. In response, Trump tweeted, “It won’t happen!”
February 2017: North Korea conducts first test under Trump’s rule
North Korea conducts a test that launched a ballistic missile into the Sea of Japan, which is the first test since Trump became president of the United States. Trump vows to deal “very strongly” with North Korea.
WATCH: Was North Korean missile test really a test of Donald Trump?
May 1, 2017: Trump ‘would be honoured to meet Kim’
In an interview with Bloomberg published May 1, Trump said he would be honoured to meet the North Korean leader.
“If it would be appropriate for me to meet with him, I would absolutely, I would be honoured to do it,” Trump said. “If it’s under the, again, under the right circumstances. But I would do that.”
July 3, 2017: Trump reacts to another North Korea missile launch
On July 3, shortly after North Korea tested another missile near Japan, Trump took to Twitter and said, “North Korea has just launched another missile. Does this guy have anything better to do with his life?”
July 26, 2017: ‘We will strike a merciless blow at U.S.’
On July 26, Kim’s regime threatened the U.S. with a pre-emptive nuclear strike if Washington attempted to remove the country’s supreme leader.
“Should the U.S. dare to show even the slightest sign of attempt to remove our supreme leadership, we will strike a merciless blow at the heart of the U.S. with our powerful nuclear hammer, honed and hardened over time,” Yonhap News Agency reported, quoting a spokesman of the North Korean foreign ministry at the time.
Aug. 6, 2017: North Korea threatens U.S. for its ‘heinous crimes’
The United Nations Security Council had unanimously voted to impose new sanctions on North Korea. In retaliation, the hermit kingdom threatened the U.S. for its “heinous crimes” (sanctions) committed against the regime.
“We will make the U.S. pay by a thousand-fold for all the heinous crimes it commits against the state and people of this country,” North Korea said through its state media.
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August 8, 2017: Trump warns he will bring ‘fire and fury’ upon North Korea
Trump warned North Korea “will be met with fire and fury” like the world has never seen, if Kim threatened the United States.
The comments were seemingly made in response to reports that North Korea has successfully produced a nuclear warhead that’s small enough to fit inside its intercontinental ballistic missiles (ICBM).
Just hours after Trump’s comment, North Korea said it was “carefully examining” plans for a missile strike at the U.S. Pacific territory of Guam.
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“The KPA Strategic Force is now carefully examining the operational plan for making an enveloping fire at the areas around Guam with medium-to-long-range strategic ballistic rocket Hwasong-12 in order to contain the U.S. major military bases on Guam including the Anderson Air Force Base,” the spokesman said.
August 11, 2017: U.S. is ‘locked and loaded’
On August 11, Trump warned North Korea that the U.S. military was “locked and loaded, should North Korea act unwisely.”
On Sept. 12, North Korea condemned the latest UN sanctions against the country and warned the United States of “forthcoming measures” by the hands of the secretive state.
North Korea’s ambassador to the United Nations Han Tae Song lashed out at the UN’s latest “illegal and unlawful” sanctions against his country, calling it a “grave challenge to international peace and justice.”
WATCH: North Korean TV shows video of latest missile launch over Japan
The North Korean ambassador went on to warn the U.S. that it will suffer consequences for the approved sanctions.
“The DPRK is ready to use any form of ultimate means,” Song said. “The forthcoming measures by DPRK will make the U.S. suffer the greatest pain it’s ever experienced in its history.”
Sept 17, 2017: ‘Rocket man’
Trump and South Korean leader, Moon Jae-In, agreed to intensify economic and diplomatic pressure against Kim, who Trump called a “Rocket Man” on Twitter.
“I spoke with President Moon of South Korea last night. Asked him how Rocket Man is doing. Long gas lines forming in North Korea. Too bad!” Trump tweeted.
Days later at a speech to the UN General Assembly, Trump said the U.S. would “totally destroy North Korea” if forced to defend itself or its allies. He also doubled down on his former comment, calling Kim a “rocket man on a suicide mission for himself.”
Sept. 21, 2017: Kim likens Trump to ‘barking dog’
North Korea compared Trump’s speech at the UN General Assembly to the sound of a “barking dog.”
The North’s Foreign Minister Ri Yong Ho told reporters that, “It would be a dog’s dream if he intended to scare us with the sound of a dog barking.”
Sept. 22, 2017: Trump calls Kim a ‘madman’
Trump took to Twitter and called Kim a “madman” who was endangering the lives of the people in his country.
“Kim Jong Un of North Korea, who is obviously a madman who doesn’t mind starving or killing his people, will be tested like never before!” the president tweeted.
Kim also called Trump a “mentally deranged U.S. dotard.” According to a blog on Merriam-Webster’s site, “Dotard, which comes from the Middle English word ‘doten’ (meaning ‘to dote’), initially had the meaning of ‘imbecile’ when it began being used in the 14th century.”
Nov. 12, 2017: ‘Short and fat’
In response to the North Korea government calling him an “old lunatic,’ Trump essentially called Kim “short and fat” in a tweet.
“Why would Kim Jong-un insult me by calling me “old,” when I would NEVER call him “short and fat?”
Jan. 2: Whose nuclear button is bigger?
During a televised New Year’s Day speech, Kim said America will never be able to start a war against North Korea now that his country developed the capability to hit all of the U.S. mainland with its nuclear weapons. He added: “A nuclear button is always on my desk.”
Trump retaliated and said his nuclear button is “much bigger & more powerful” than Kim’s.
WATCH: Kim Jong-Un warns U.S. that he has ‘nuclear button’ on his desk
March 8: Trump agrees to meet North Korean leader
Signs of a thaw emerged in the new year, with North and South Korea resuming talks and North Korea attending the Winter Olympics.
Kim also expressed an interest in meeting Trump, who praised the “great progress” on relations between the two countries. Trump then stunned the world by agreeing to meet Kim.
April 25: Trump calls Kim ‘very honourable’
Ahead of the June summit, Trump said Kim had been “very open” and “very honourable.”
“We have been told directly that they would like to have the meeting as soon as possible. We think that’s a great thing for the world,” Trump said. “Kim Jong Un, he really has been very open and I think very honourable from everything we’re seeing.”
WATCH: The bizarre circumstances around Trump/Kim meeting
May 24: Trump cancels summit with North Korea
Trump abruptly cancelled the meeting between the U.S. and North Korea. He issued a letter that said: “Based on the tremendous anger and open hostility displayed in your most recent statement, I feel it is inappropriate, at this time, to have this long-planned meeting.”
June 1: Trump confirms summit back on
Trump confirmed the summit was back on.
“I think it’s probably going to be a very successful, ultimately a successful process,” Trump told the media. “It’s going to be a process, but the relationships are building and that’s a good thing,” Trump said.
June 11: Trump excited to be in Singapore
The day before Trump is expected to meet with Kim in Singapore, the president tweets: “It’s great to be in Singapore, excitement in the air!”
— With files from Global News’ Adam Frisk and the Associated Press
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