We only have snippets of information of Kim Jong Chol, the middle son in the family and the oldest born to Kim Jong Il’s favored, third mistress, Ko Young Hui. Jong Chol was given prominent positions in the Hermit Kingdom’s Orwellian-named Organization & Guidance and Propaganda & Agitation departments, a sign that he was being groomed for bigger things. But according to a memoir published by an anonymous Japanese chef who once served the regime, Kim Jong Il looked upon his middle son with distaste, considering him too “unmanly” and “effeminate” to take up his crown. He was allegedly spotted, as pictured above, attending an Eric Clapton concert in Singapore earlier this year.
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.