Conor McGregor was all smiles when he met Vladimir Putin at the 2018 World Cup final in Moscow.
Following the Russian President's decision to invade Ukraine, video footage and photos of the UFC star meeting Putin has emerged online once again.
McGregor was warned not to put his arm around Putin as they posed for a photo at the Luzhniki Stadium.
A clip of the meeting was shared on McGregor's Mac Life website at the time.
McGregor quickly took his arm away as his facial expression changed before he held his two hands in front of himself for a snap prior to France's 4-2 win over Croatia.
But, he later uploaded pictures on Instagram and described Putin as "one of the greatest leaders of our time".
He posted: "Today I was invited to the World Cup final as a guest of Russian President Vladimir Putin.
"This man is one of the greatest leaders of our time and I was honored to attend such a landmark event alongside him.
"Today was an honor for me Mr. Putin. Thank you and congratulations on an amazing World Cup."
McGregor gifted Putin a bottle of his Proper 12 Whiskey when they met, but revealed in 2019 that he never heard back if the Russian leader liked it.
He said at a press conference in Moscow: "Many people don't know, the very first bottle of Proper Twelve Irish whiskey, I gifted to Vladimir Putin.
"President Putin's security detail is second to none as I'm sure you know, you don't mess around with Vladimir.
"So, I gifted the bottle and I gifted it to his security.
“They had to take the liquid from the bottle to make sure the liquid was safe and it was not maybe poisoned or what not and then it was gifted to Vladimir Putin.
"I haven't got to speak to him since to see what he thought of it, although I'm sure he did have a taste and I'm sure he enjoyed it."
McGregor's biggest UFC rival is undefeated Russian fighter Khabib Nurmagomedov, who met with Putin after starting a brawl following his 2018 win over the Dubliner.
And Putin sympathised with Nurmagomedov over the incident, during which the 33-year-old jumped into the crowd in Las Vegas and began fighting with McGregor's teammate Dillon Danis.
A number of the Eagle's team also attacked McGregor inside the octagon at UFC 229.
Putin congratulated his fellow countryman following the bout, saying: “Anyone could have jumped [out of the octagon] in the same way.
“If we are attacked from the outside, not only you, we could all jump in such a way … there could be hell to pay.”
But Putin added: "It’s better not to reach that stage."
Nurmagomedov apologised for his actions and said to Putin when they met that his father and trainer, the recently-deceased Abdulmanap, would likely “smash" him when he returned home.
Putin responded: "I will ask your father not to punish you too strictly, because you achieved the main task, worthily and convincingly."
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