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04/10/2013 04:49 pm ET

Kim Jong Nam, Kim Jong Un's Brother, Could Have Been Supreme Leader Of North Korea

Sometimes it can be hard not to look back in time and wonder, "What if?"

We found ourselves doing just that after Mental Floss published a short but fascinating portrait of Kim Jong Nam, the half-brother of North Korean Supreme Leader Kim Jong Un. The article painted a picture of Kim Jong Nam as a fun-loving playboy with a refreshing habit of speaking the truth about North Korea's secretive ruling family.

Kim Jong Nam, the love-child of an illicit affair the regime's former dictator Kim Jong Il had with a North Korean actress, was once the top contender to succeed his father in the role of Supreme Leader, according to The New York Times. But an embarrassing incident at a Japanese airport -- Kim Jong Nam tried to use a fake passport to go to Tokyo Disneyland -- along with his "voracious appetites for alcohol and women" made his father doubt Kim Jong Nam's ability to lead, the Times reported.

Still, Kim Jong Nam, who is 42 and reportedly living in Singapore with his family, doesn't seem all that upset about being passed over for the position.

He's spent much of the past few years in Macau, a seaside gambling town in southern China that he likes because "it's the most free and liberal place" near where his family lived at the time. (He and his family reportedly left China for Singapore in early 2012 out of fear for their safety, South Korean newspaper Chosun Ilbo reports.)

"Because I was educated in the West, I was able to enjoy freedom from early age, and I still love being free," Kim Jong Nam reportedly said, according to a book written by Yoji Gomi, a Japanese journalist who corresponded with him for several years.

Kim Jong Nam's relative freedom has allowed him to speak his mind about the North Korean regime with a candor most North Koreans will never enjoy. He once called the country's practice of passing power down through the ruling family "a joke to the outside world," according to Gomi's book. He also reportedly cast doubt on whether his younger brother, Kim Jong Un, had enough experience to lead.

Still, Kim Jong Nam can't say too much else about his now-infamous brother; the two have reportedly never met.

What if this straight-talking playboy had been chosen to lead North Korea instead of his pugnacious little brother? Would North Korea still be singling out cities like Austin, Texas, for missile attacks? We'll never know.

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