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SINGAPORE - JUNE 12: In this handout photo, North Korean leader Kim Jong-un shakes hands with U.S. President Donald Trump during their historic U.S.-DPRK summit at the Capella Hotel on Sentosa island on June 12, 2018 in Singapore. U.S. President Trump and North Korean leader Kim Jong-un held the historic meeting between leaders of both countries on Tuesday morning in Singapore, carrying hopes to end decades of hostility and the threat of North Korea
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(CNN) —  

President Donald Trump caught the world by surprise late Thursday with his stunning announcement that he would accept North Korean dictator Kim Jong Un’s invitation to meet sometime between now and May.

Assuming that the meeting actually happens, Trump will be the first sitting president to speak with – either in person or by phone – a North Korean leader.

Whether you like Trump or hate him, you can’t conclude anything other than this is a massive, massive gamble – the likes of which we haven’t seen from an American president, diplomatically speaking, in a very long time.

In retrospect, it actually makes perfect sense that Trump is willing to roll the dice on such a massive stage. The move to meet with Kim is actually something very close to the Platonic ideal of Trumpism.

Here are five reasons why:

1. Trump the deal-maker: When Donald Trump looks in the mirror, he sees someone who is uniquely able to bring people together who have never come together before – and put a deal together. He believes himself to be one of the great dealmakers in history. As such, he has to try to tackle the biggest dealmaking challenges in the world. And finding a way to a more stable and de-nuclearized North Korea is about as big as they come.

2. Trump the history-maker: Peppered into almost every single one of Trump’s speeches is some phrase like “never been done before” or “historic,” “biggest” or “first.” He loves to go where no one has gone before – or, at least, where he believes no one has gone before. (He also has a tendency to say he is making history – largest inauguration crowd ever, etc. – when the facts suggest he isn’t.) The chance to be the first sitting American president to sit down with Kim was simply too appealing to Trump’s love of “firsts” to possibly pass up.

3. Trump the unorthodox: Trump revels in the idea of freaking out the political establishment, doing something that everyone in Washington will fret about while he will just go do it. He loves to freak out the squares. It appeals to his lingering sense that the smart people aren’t all that smart. And his bitterness about never being included in the “cool kids” club. There’s an element of “wait until they get a load of me” in Trump at all times.

4. Trump the freelancer: In the opening to the “Art of the Deal,” Trump wrote about how he liked to start his day – clean desk, empty schedule. He didn’t like to make plans. He liked to react at whatever the day threw at him. His grand strategy was just a bunch of tactics sewed together. Trump has brought that same mentality to the White House. Trump has bridled under attempts by his staff to keep him on message for a day or even a week. He values his “Executive Time,” when he putters around the residence, watching television and tweeting. He trusts his gut – even if it says something different than all the eggheads in his administration.

5. Trump the reality TV star: Trump’s background as a reality television show star and producer is never far from his mind. Trump knows that a meeting between him and Kim will have the eyes of the world on it. Heck, even the announcement of the meeting was straight out of the reality TV playbook – “Stay tuned for a big announcement later tonight!” Given the number of potential eyeballs who will be watching the Trump-Kim meet-up, it was literally an opportunity Trump could never (and would never) pass up.