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5 year oldBack in April 2016, after a disagreement over promotional responsibilities, the UFC pulled the Irishman from the main event slot at UFC 200 and McGregor infamously tweeted: "I have decided to retire young. Thanks for the cheese. Catch ya's later."
The media pounced on the story, reporting the early retirement of the sport's biggest star. But it turned out McGregor wasn't retiring at all. He was merely using his star power as leverage to get him the fight - and the deal - that he wanted. And as a result he faced Nate Diaz in a huge rematch at UFC 202 later that year.
All good negotiators know when to walk away from the table, and McGregor has proved down the years that he's certainly a formidable negotiator. He used those skills to great effect back in 2016 and it worked out incredibly well for him. Now there's a very strong chance that he's looking to repeat the trick by threatening to walk away again.
However, McGregor has made no secret of his desire to come back. He's offered to fight Anderson Silva in Brazil. He's hinted at a possible trilogy fight with Nate Diaz and he's enjoyed multiple good-natured social media skirmishes with current UFC featherweight champion - and former McGregor victim - Max Holloway. Then there's the unfinished business with the man who so comprehensively defeated him in his last outing at UFC 229, current UFC lightweight champion Khabib Nurmagomedov.
All signs seemed to point to a McGregor return in July at UFC 239, during the organisation's annual International Fight Week festivities. A bout with fellow fan favourite Donald "Cowboy" Cerrone was mooted but then seemingly scrapped, with Cerrone suggesting McGregor wouldn't accept co-main event billing. Now McGregor says he's calling it quits.
Given the above, McGregor's retirement announcement seems to fly in the face of all the noises we've heard from him since his defeat by Nurmagomedov, and suggests he's trying to put the squeeze on the UFC again.
However, the last time he tried, the UFC was run by the Fertitta brothers, who were sympathetic to the Irishman and keen to keep their biggest star on board before the UFC's record-breaking $4bn (£3.2bn) sale.
But now the UFC is run by sports PR and management giants Endeavor, whose figurehead Ari Emanuel (the real-life inspiration for Entourage's Ari Gold character) is known as one of the toughest negotiators in the business.
However, it's worth noting that McGregor has fought just once for the UFC since their takeover, and having the Irishman compete will certainly do no harm to the company's bottom line. That may well be uppermost in McGregor's mind if he's looking to strike another lucrative deal.
The flipside to this whole argument, of course, is that McGregor really has called it a day.
And if he truly has decided to step away for good, then he leaves the sport of mixed martial arts after a career inside and outside the cage that truly matches his fighting moniker - "Notorious".
Regardless of whether he opts to hang up his gloves or carry on, McGregor has already delivered a host of unforgettable moments inside the cage during his career.
The KO that started it all - v Ivan Buchinger, Cage Warriors 51, December 2012
Arguably the most important single punch in Conor McGregor's career came back at Cage Warriors 51 on New Year's Eve, 2012, when a pinpoint straight left spectacularly knocked out Ivan Buchinger as the Dubliner captured the Cage Warriors lightweight title to become a two-division champion for the European promotion. That KO, and the wild scenes in the crowd, created the spark that eventually led to McGregor being signed by the UFC.
The dream debut - v Marcus Brimage, UFC Stockholm, April 2013
McGregor's first assignment was, on paper, a tricky one. Marcus Brimage had graduated to the UFC from The Ultimate Fighter and was riding a four-fight win streak. But McGregor put him away with ease, finishing the American with a slick combination of punches in a nerveless debut that offered a glimpse of what was to come.
His coming out party in Dublin - v Diego Brandao, UFC Dublin, July 2014
UFC Fight Night in Dublin in July 2014 was the perfect storm for McGregor - and for Irish MMA at the time. Each and every Irish fighter delivered the goods in Dublin to raise the atmosphere to fever pitch by the time McGregor entered the cage to face dangerous Brazilian Diego Brandao. Fired up by the crowd, yet still as cool as a cucumber, McGregor finished Brandao in just four minutes, five seconds amid some of the craziest scenes ever seen at a UFC event. If there was any doubt before, the UFC officials knew at that moment - they had a bona-fide superstar on their hands.
His first UFC title - v Chad Mendes, UFC 189, July 2015
After a lengthy world tour to promote his first world title bout against Brazilian world champion Jose Aldo, the defending champion pulled out with a rib injury. But rather than keep his powder dry for another day, McGregor happily accepted a short-notice fight with top contender, American Chad Mendes, at UFC 189 in July 2015. Many believed Mendes' wrestling-based style would prove to be McGregor's Kryptonite but, despite being taken down during the contest, McGregor bounced back to claim a thrilling second-round TKO finish to capture the UFC interim featherweight title.
Gone in thirteen seconds - v Jose Aldo, UFC 194, December 2015
After his stunning win over Mendes, the matchup with undisputed champ Aldo became even bigger than before, and their meeting at UFC 196 in December 2015 was, at that time, the most anticipated fight in UFC history. Before the fight, McGregor predicted he would lure Aldo in, force an error, then strike. And that's exactly what happened. In the very first exchange of the fight, Aldo came out uncharacteristically aggressively and McGregor timed a left hand to perfection, knocking the Brazilian cold with one shot and capturing the UFC featherweight title in the process. The time on the clock? Just 13 seconds.
The "Champ Champ" - v Eddie Alvarez, UFC 205, November 2016
After swapping wins in a pair of thrilling Las Vegas non-title fights with Nate Diaz, McGregor took on reigning UFC lightweight champion Eddie Alvarez at the UFC's first-ever show at Madison Square Garden. And the Irishman rose to the occasion, knocking down the champion five times en route to a second-round TKO finish as he captured the UFC lightweight title to become the first athlete to hold UFC titles in two weight classes simultaneously. If his retirement announcement proves to be true, his triumph in New York will go into the record books as his final win inside the UFC octagon.