A timeline of crumbling friendship between Conor McGregor, Artem Lobov

The once-ironclad friendship between former two-division UFC champion Conor McGregor and Artem Lobov is over. The pair have entered into a legal battle over McGregor's Proper No. 12 Irish Whiskey, which Lobov insists he was instrumental in creating. 

That suit has led to fight callouts, Twitter rants and defamation claims. 

Here's a timeline of a crumbling friendship. 

2015: Lobov appeared as a cast member of "The Ultimate Fighter 22," a UFC-produced reality TV series in which McGregor served as a coach. Lobov was eliminated in the first episode but was brought back in the second episode. Each coach could pick one fighter to return. McGregor picked Lobov, who lost in the finale to Ryan Hall. 

2018: During the UFC 223 fight week in New York, a video surfaced of Russian UFC star Khabib Nurmagomedov confronting Lobov in the fighter hotel. Nurmagomedov puts his hand on Lobov's neck. The video went viral.

After he saw the video hours later, McGregor traveled from Ireland to New York, where he threw a dolly through a bus window looking to confront Nurmagomedov and defend Lobov. That incident spurned one of the more volatile feuds in UFC history.

2019: After announcing his retirement from MMA, Lobov stepped into the BKFC ring to face off with McGregor's rival, Paulie Malignaggi. He won as an underdog and then revealed how proud McGregor was of him. 

“I spoke to Conor, he said that was a good performance. I dominated the fight. I pressed the action all the time and he said it was a very good performance and a great win for me,” Lobov said on the MMA Hour (h/t Irish Mirror) after the performance.

July 10, 2021: Lobov shared a flashback photo of himself and McGregor together on the day of his rematch with Dustin Poirier.  

"Redemption was got that night and redemption will be got tonight!! Lets go brother!!!" he wrote in the caption. The friendship seemed solid. 

August 2022: In an interview. Lobov revealed his role in the creation of McGregor's Proper No. Twelve Irish Whiskey. 

“The selling point of my book will be the Proper 12 Whiskey story. A few people know, but this was actually my idea. I was the person who came up with the idea to do a whiskey for Conor,” Lobov told talkSPORT.