The Most Senior Obama Administration Official to Have Met Kim Jong Il Is …
… Under Secretary of State for Political Affairs Wendy Sherman, who traveled to Pyongyang with then-Secretary of State Madeleine Albright in 2000 when she was President Clinton's special adviser on North Korea. She's now a top aide to Secretary of State Hillary Clinton and is said still to have a hand in the North Korea portfolio.
The reclusive and eccentric North Korean leader rarely left the country and rarely welcomed U.S. delegations to Pyongyang. Former Presidents Jimmy Carter and Bill Clinton both met with him, but only after they left office.
Before joining the administration in September, Sherman still worked with Albright and she's quoted in a number of Kim Jong Il obits today, presumably because they were prepared some time ago before she rejoined government.
In the New York Times, she describes Kim as "smart, engaged, knowledgeable, self-confident, sort of the master-director of all he surveyed."
"At the time, there were a lot of questions in the U.S. about whether he was really in control, and we left with no doubt that he was," she told the Times.
She added, however, that Kim was "a conceptual thinker."
Sherman is also quoted in an NPR obit on Kim Jong Il in which she described him as "smart and a quick problem-solver. … He is also witty and humorous. Our overall impression was very different from the way he was known to the outside world."
Sherman sat next to Kim during the Mass Games, the huge festival in North Korea that features synchronized dance routines. Even Albright remarked out loud how impressive they were (she retracted that after the media slammed her for pandering to the repressive regime). Sherman said she believes Kim must have been a "great director" in a previous life, NPR reported.