Retired US basketball player Dennis Rodman is taking a team to North Korea for a match marking leader Kim Jong-un's birthday.
He has formed a close friendship with Mr Kim, an enthusiast of the sport, and has described his trips to Pyongyang as basketball diplomacy and he aimed to "connect two countries".
Rodman and the team of former US National Basketball Association (NBA) players flew from Beijing on Monday ahead of Wednesday's match, the BBC reports.
State Department officials have made it clear that Rodman does not represent the United States.
The sportsman has been strongly criticised for ignoring North Korea's human rights abuses. Rodman last visited North Korea in December last year, shortly after the execution of Chang Song-thaek.
The fall of Kim Jong-un's once-powerful uncle was seen as a major shake-up at the very top of Pyongyang's elite.
On that visit - Rodman's third - he did not meet Mr Kim. He has met the young leader on his other two previous visits, however, and is the highest-profile American to have done so.