Transcript for Inside Kim Jong Un's strategy for Trump meeting

We'll come back to you later. Want to bring in Martha Raddatz also here with me right now. Let's talk about Kim Jong-un. He got here today because he accelerated the nuclear program. The big question, can he give it up? What does he need in return? He says he will talk denuclearization but as you know all the experts say he probably won't do it but what he wants, what he needs right now is security. This is the farthest Kim Jong-un has ever been from home as leader and while he may seem relaxed and at ease, the weight on his 34-year-old shoulders is tremendous. North Korean state media reporting that Kim is prepared to talk about denuclearization and peace, certainly seen as a good sign by the U.S. And that he's looking for security guarantees and economic help his nation so desperately needs. North Korean media also broadcasting images of Kim's journey surrounded by that hand-picked squad of flawless bodyguards raised from childhood to protect their leader. The straits times reports one of his plane's cargo included luxury cars and food items, that handshake and sit-down set to take place at the five-star cappella hotel, initially just president trump and chairman Kim and their translators. The two leaders are meeting tomorrow and will be master disrupters in many ways where they go off script. Reporter: Insults and a dramatic pivot as he showed surprising skill on the world stage all driving to this hoist toric moment. This the spigot has turned on for greater international engagement, economic, political, otherwise, that boosts Kim's legitimacy so in that way, you know, Kim can rack up that sort of win. Reporter: As I found on the north/south Korean border this weekend the mere fact that they're meeting instead of threatening fire and fury is also seen as a win by those who would be most affected. And we are joined here now by Tom Bossert, our newest ABC news contributor just left the trump white house as a national security aide. It's been so clear that president trump has been seized by this issue ever since that meeting with president Obama right after the election just two days after the election where president Obama said this is your number one job. Yeah, it's true, George. The president was gripped by that because it was a very sobering entry into the presidency but, remember, he's been thinking about it through the election and probably thinking about it through his entire life. The last three have seen the evolution of this problem. One saw the evolution of the fuel cycle, the second saw the evolution of the missile technology and what president trump has inherited is a world problem. It's so clear president trump sees this as his moment, his moment to be a man of history. I think he does but also think it's been heaped upon him so at this point he deserves credit for taking this on for the world because no no longer a U.S. And regional issue. If he doesn't solve it his fear there's no other way out. How do you manage the fact this has been an issue that's bill up with a lot of history over years and years and years and the president's desire to go in there and be guided by his gut. In a lot of ways it fits into his thinking because he can't tiptoe into it. He can't tiptoe through it. We've seen that process fail before and so it really lands to his strengths. He has too do it quickly in a brash fashion and looking for a strategic decision, so in a lot ways it's kind of understandable he thinks he'll figure this out in the first few minutes. Martha, you've spent a lot of time on the border and with the military in South Korea. Make no mistake about it at the beginning of this administration when Kim was accelerating his nuclear program we got close to military action. Oh, so close, George. And they were practicing and rehearsing and doing exercises in secret bunkers, pacific command, near the border, they had to get this right but the results of any kind of engagement were terrifying. There would be U.S. Losses there with our troops in South Korea. Thousands of them, so they took this very seriously. They still take it very seriously. That's the point because everyone is hoping for success tomorrow here in Singapore. The risks of failure as I said right at the start are so high. So enormous. If this fails I think you'll go right back to where we were before. I think one key point in in that we forget is that president trump is faced with a nuclear armed North Korea that can reach the United States or is just about to get there. That is why we are here today. Tom Bossert and Martha Raddatz, thanks very much.

This transcript has been automatically generated and may not be 100% accurate.