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Now young North Korean leader Kim Jong Un looks set to achieve the longstanding dream of his family dynasty -- a face-to-face meeting with a sitting US President.
But from the moment Trump steps into the room with Kim, experts said North Korea has already cemented its greatest victory -- the talks themselves.
"To have a summit with a US President is something that many countries aspire to. So for North Korea, for a tiny country which is technically still at war with the US, for their leader to sit down with a president is huge deal," Jean H. Lee, a North Korea expert at the US-based Wilson Center, told CNN.
Lee said Kim's father and grandfather would be "incredibly proud" to see their progeny establish North Korea as legitimate state on the world stage.
"Kim Jong Un is following through on the final steps his grandfather wasn't able to accomplish, and that's part of cementing his place as the third Kim to rule the country," Lee said.
Veneer of respectability
But a meeting with a sitting US President would give Pyongyang a new veneer of respectability, experts said. "It represents a number of things -- the acceptance that North Korea is there, that it's a state, that its leadership is a world leadership," Jim Hoare, former British charge d'affairs to North Korea, told CNN.
Members of the Kim family have met with ex-presidents before. Former President Jimmy Carter met with Kim Il Sung, Kim's grandfather, in 1994, while former President Bill Clinton met Kim's father, Kim Jong Il, after he left office in 2009.
Clinton came close to meeting with Kim Jong Il while still in office in 2000. But he ultimately decided to turn down an invitation to meet with North Korea's then-leader, after determining that Kim couldn't be trusted.
"President Clinton wisely said 'I am not going until this is prepared, I am sending the secretary ... That didn't thrill them,'" Albright said in Brussels in March.
Solidifying his rule
Once the summit takes place, however, there are many other potential benefits from a North Korean perspective, experts said, first and foremost of which is the safety of the regime.
North Korea is still technically at war with both South Korea and the United States -- Pyongyang sees the latter as the biggest threat to its government. Any peace treaty with the South, and the benefits that would bring, would require Washington's approval.
"There's a strong belief within North Korea ... that if only the United States would stop its hostility then North Korea would be safe, no one else would interfere," Hoare said.
Gaining a break in sanctions or assurances of safety from the United States would be a major victory for Kim, and the North Korean leader may be enthusiastic for a clear win as he tries to hold his troubled regime together.
Lee said while it is always incredibly difficult to read the power dynamics of the North Korean regime from outside the country, Kim was a young leader who had to set up a power base to potentially rule for decades.
"He is a young man who took power quite abruptly with the death of his father, so it's hard to imagine that he wouldn't have any challenges or feel insecure," she said.