Transcript for Dennis Rodman on his relationship with North Korean leader Kim Jong Un: Part 3

Reporter: December, 2011. North Korea says goodbye to dear leader Kim Jong il, as 27-year old Kim Jong un, one of the pallbearers at his father's funeral, assumes the leadership of his country. But he is as much a mystery to north Koreans as he is to the west, who hope he will herald change. I don't think we know too much about this person that's the leader of North Korea right now. Reporter: But one thing is clear Kim takes a very different public path than his reclusive and eccentric father, patterning himself instead on his legendary grandfather Kim il sung. It is no accident that Kim Jong-un has put on all this weight, and has got the same haircut, and very often wears the same clothes as his grandfather. And smiles the same. Smiles the same, everything is very obviously designed to remind north Koreans that, you know, not only does he have this divine right to be the leader of North Korea, but that he can make life better for north Koreans. There he is. Waving out to the crowd. Reporter: During my reporting trips to North Korea, I was never allowed to get close to the enigmatic leader. Have to stay within five feet of each other? Here, when he suddenly showed up at this museum opening and caused a frenzy among the press, we didn't a chance to ask any questions. It turns out, one outsider with firsthand knowledge and personal contact with the north Korean leader isn't a diplomat or an American spy. It's this man. The only American known to have become close to Kim after he assumed power. The flamboyant former NBA star and Chicago bull Dennis rodman. His latest attempt to get into North Korea, sponsored by a company called potcoin. Rodman made international headlines when he visited north Korea in 2013 along with a vice TV crew, at the invitation of the Chicago bulls-obsessed leader. At a goodwill basketball game, rodman was seen talking intently with Kim. Later, rodman and his entourage got the surprise of their lives, an invitation to party with the mystery man. So since you had the chance to, I mean just to shake his hand and talk to him. How is his English? Did you speak English to him? He said hi. He said okay now. But, but he has no, no English at all. So it looks, I mean it looks like you guys are talking here but this just, he's just speaking through his interpreter. No his, so every time we - you see us talk like this, we're talking about basketball and he always asked me, said, "Dude, I would love to go to New York, but I can't." He says stuff like that. What was he like? Did he seem serious or. He's always smiling, man. He's all, he's always smiling. Especially when we -- you're around his, his comfort zone. In terms of basketball, did he play basketball at all? He said Dennis, let's play horse. So we go to free throw line. He hits that. I said all right. I missed the free throw, of course. And then next thing you know, he goes on other side of the corner over there, and he hits. I said dude, this guy can shoot. Reporter: Rodman has visited Kim three times now. And was one of the privileged few allowed to visit that luxury resort that Kim used to visit as a child. He rode horses with the dictator, met his wife and baby daughter, and partied late into the night. It was like 70 people at this big round table, man, like wow, I mean. And everybody had they turn with, they had a shot of vodka. Take a vodka shot. And then they'd try to say karaoke it was like with, with, a round table. It's 70 people trying to sing karaoke. How is he as a singer? He's pretty good. What did he sing? He was singing Frank Sinatra, "My way". He sang "My way"? Yeah, he had this girl band. Like 14 girls. They travel with him everywhere, to play his music and stuff. So he had the lyrics and a screen. He was reading it in English. Nah. He would do, he was singing it in, in all Korean. Reporter: Rodman makes no apologies for his embrace of a dictator who lives the high life while so many of his countrymen suffer in misery. It's a friendship hug. You rarely see this in the world. Even with his grandfather and father. You don't see the leaders do this, especially an African American. You never see this in the north Korea. But it's a country with a lot of starvation now, too though. Is that okay? Well, you know, a lot of, a lot of people in the world are starving. Even though they say he's a bad man but he, to me, he's not a bad man. I didn't see that part. Reporter: Rodman may not think Kim's bad, but there's someone else who has serious concerns about him. His errant and disgraced half-brother Kim Jong nam. He and his family are living in the tiny Chinese territory of macau, known as a Mecca of gambling and glitz. The city provided security. Many people I talked to in macau believed that um, Kim jong-nam and his family were in macau under beijing's protection. Reporter:ut even in exile, Kim jong-nam still worries about the fate of the north Korean people under the rule of his half-brother. And perhaps unwisely, he begins speaking out. In Tokyo, I met one of the few he confided to -- Japanese journalist yoji gomi. How did you get a chance to meet Kim Jong nam? I came across him at beijing airport. I am very surprised, I start interviewed him, a lot of questions at the time. Reporter: Gomi landed a rare interview with the elusive Kim at a macau restaurant. I learned a lesson not to do reckless and immature acts. I made a big mistake so it somehow aroused father's anger. Reporter: But perhaps the most reckless of his acts was criticizing his brother's rule. In a series of published email exchanges with gomi, Kim wrote: "The Kim Jong un regime will not last long. Without reforms, North Korea will collapse, and when such changes take place, the regime will collapse." Kim Jong nam said to me, North Korea should be reformed and make north Korean people more rich and happier. It's a message to Kim Jong un. Reporter: But do those comments make Kim Jong nam a marked man?

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