Dennis Rodman is at it again, talking about two of his favourite subjects: sports and North Korea.

The celebrity gossip website TMZ caught up with the former NBA star this week as he got on to a bus, and it was evident that he believes his sporting relationship with the country is still going strong.

Dodging questions about North Korean leader Kim Jong-un’s recent time out of the public eye, Rodman said that he would be returning to the peninsula in November to bring pro-wrestling to the North.

It was unclear whether Rodman knew that he is not the first to have this idea. Earlier this month a throwdown, organised by a Japanese wrestler-turned-MP, saw North Koreans wrestlers line up against an international competitors in front of dozens of reporters, tourists and celebrity guests.

In 1995 Collision in Korea was the largest pay-per-view event in the history of pro-wrestling. It attracted a crowd of 340,000 people and was described by one of the news anchors at “wrestling and diplomacy at it’s best.”

Critics have previously dismissed the Kim Jong-un-Dennis Rodman relationship as ego-driven, dysfunctional and damaging for diplomatic relations. He has skirted around the human rights issue during his previous trips, and got himself tangled up in the case of Kenneth Bae – the American serving 15 years hard labour in North Korea for crimes against the state.

If the claim comes good, it will be the fifth big trip for Rodman to the country in just under two years. We take a look back at his most prolific visits, what he said and how the world reacted.

February 2013

Rodman makes headlines by arriving in North Korea with a group of players for the Harlem Globetrotters and a Vice film crew for some self-styled “basketball diplomacy”.

Rodman and Kim watch basketball together and the visiting entourage was reportedly treated to alcoholic drinks provided by the leader. Rodman tells Kim “you have a friend for life”.

The trip took place amid continued hostility between the US government and North Korea. An official statement from the White House said that it was “inappropriate” for North Korea to have spent money on such a big spectacle when people were being starved and denied their human rights. When asked about the trip secretary of state John Kerry said: “You know what? Dennis Rodman was a great basketball player, and as a diplomat, he was a great basketball player. And that’s where we’ll leave it”.

Whilst Rodman is there he also makes internet history becoming one of the first to tweet from the country on a 3G network newly opened for foreign tourists, using the hashtag #WORMinNorthKorea (Worm being his nickname from his basketball playing days).

It's true, I'm in North Korea. Looking forward to sitting down with Kim Jung Un. I love the people of North Korea. #WORMinNorthKorea — Dennis Rodman (@dennisrodman) February 26, 2013

September 2013

A few months later Rodman was back again but this time it was a more low-key affair. “The Marshal Kim and I had a relaxing time by the sea with his family” said Rodman, before accidently announcing to the world the name of Kim’s daughter: Ju-ae.

Leaving Vice behind (the regime wasn’t happy about the negative coverage from his last visit, according to Buzzfeed), Rodman finds new facilitators led by Michael P Spavor, a consultant specialising in sports and cultural exchanges with the DPRK.

Spavor’s website features him enjoying a few laughs with Kim Jong-un, and he describes September’s trip as “a blast”.

December 2013

Squeezing in a last trip in 2013 Rodman arrived back in North Korea in December for a sponsored trip to help train the North Korean basketball team in preparation for the leader’s birthday.

Rodman’s team arrive shortly after the dramatic, highly publicised execution of Kim’s uncle Jang Song-thaek: thought to be a strong message from the regime about the importance of absolute loyalty.

Ahead of the trip, Rodman says he does not intend raise the issue with the leader because he doesn’t want to exploit his friendship for political reasons, but then refuses to say whether the pair even met up on his return. Shortly after, the sponsors, Paddy Power, pull out in “reaction to the worldwide focus and total condemnation of the North Korean regime over recent events”.

January 2014

In January, Rodman is back – again – with a team of NBA players to perform an exhibition game, a birthday present to Kim Jong-un. Not content with the basketball spectacle, Rodman takes to centre court to sing a quick happy birthday is hushed tones in front of the crowds applauding uniformly.

This time it’s the NBA who speak out against the Rodman show, arguing that “birthday parties for dictators that torture and kill” should not be thought of as sports diplomacy.

Rodman also found himself again embroiled in controversy around American prisoner Kenneth Bae, whose detention is a tense sticking point between US and North Korea. In May 2013 he had tweeted that he would ask his friend Kim to “do me solid and cut Kenneth Bae loose”. In September, he backtracked, saying it was the job of then-US secretary of state Hillary Clinton and president Barack Obama to sort it out.

After the January trip he was questioned again about Bae, and attempted to blame Bae and his actions in North Korea for his detention. Bae’s sister condemned Rodman saying: “This isn’t some game. This is about a person’s life – father of three, a son and a brother and a husband.”