Rodman reportedly visited North Korea at least four times - his last trip being in 2014 where he and former NBA All-Stars played an exhibition game as a "birthday present" for the country's leader, Kim Jong Un. A senior USA official said the State Department was aware Rodman was planning to travel to North Korea, but stressed he is not there in any official capacity.
Rodman was spotted heading towards a North Korea-bound plane at Beijing International Airport today.
Still, his latest foray comes amid heightened tensions between Washington and Pyongyang over a series of missile tests in defiance of United Nations sanctions, as North Korea seeks to develop a rocket capable of carrying a nuclear warhead to the US mainland.
Rodman, who has met with North Korean leader Kim Jong Un on past trips to Pyongyang, declined to answer questions when he was seen by CNN reporters at Beijing International Airport, the network said.
Rodman has traveled to North Korea before, though he has been criticized for comments he made on previous trips.
Rodman routinely distances himself from political events in North Korea.
That said, he has visited the country multiple times in the past, and now it has been reported that he will once again make his way there.
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In a tweet posted on Tuesday morning, Rodman confirmed what will be his fourth visit to the secretive east Asian state, saying he "will discuss when I return".
The North has occasionally jailed United States citizens on charges ranging from hostile acts to illegal entry, and released them only after visits by high-profile figures including former president Bill Clinton.
Asked if he would talk to North Korean leader Kim Jong Un about several Americans detained there, he said "that's not my objective right now".
The one-time National Basketball Association great has visited the nation on four separate occasions, CNN noted, but has never traveled in any official capacity for the United States. He's described those visits as a "basketball diplomacy project".
"I know Dennis would do anything for President Trump, he knows him personally so we would go back in a second if it meant helping everyone in uniform, helping our president, helping our nation", Chris Volo, Rodman's minder said at the Westpoint event.
Rodman had earlier appeared on Celebrity Apprentice in 2009, with Trump calling the basketballer "a piece of work".
The colourful sportsman sang Happy Birthday to the leader, but his side were defeated by the North Koreans.