The eldest son — Jong Nam’s mother was Song Hye Rim, a celebrity North Korean actress who was initially Kim Jong Il’s secret mistress — Jong Nam was groomed for succession until the awkward day in 2001 when he was seized by Japanese authorities for trying to enter the country on a forged Dominican Republic passport. Jong Nam allegedly told police there ahead of being deported to China that he simply wanted to visit Tokyo Disneyland. The incident, coupled with the rumored defection of Jong Nam’s mother (she died in Russia in 2002), led to his estrangement from his father. Jong Nam would take up residence in the casino mecca of Macau and gain notoreity for his gambling habits and hard-drinking. In 2007, TIME and Global Spin’s Austin Ramzy and Ishaan Tharoor came across his house tucked away in a quiet gated community on the black-sanded island of Coloane. No one answered the door, but hung prominently by a window was a picture of a sunflower bending to the sun’s rays — a sign, even in reported exile, of Jong Nam’s filial duty to his now deceased father.
After Kim Jong Il: A Look at the Kim Family Tree
The heavy-jowled Kim Jong Un looks poised to succeed his father. But he was not always the most likely: TIME looks at those in the Kim clan who may have had (or still possess) designs on the Hermit Kingdom's top job.