It’s finally happening. After nearly five years away from the Octagon, Conor McGregor is set to run it back with Max Holloway, more than 13 years after their first clash. But with so much time spent outside the cage and questions surrounding McGregor’s lifestyle, not everyone is convinced the comeback story ends well. During the ‘Deep Waters’ segment of UFC on Paramount+, Jorge Masvidal and Chris Weidman predicted the Irishman’s fate.
“It’s also the lifestyle,” Masvidal said. “I think Conor lives a certain lifestyle we’ve all seen, and you can tell it’s not for show and it’s really his lifestyle… Max lives a completely different lifestyle. I’ve never seen Max at the club drunk. You never see him in the headlines for anything bad. That guy lives a different life where he is in the gym, family, gym family…
“I think that’s gonna pay the biggest dividends. Cause you can be away from the sport for five years and come back [as if] nothing happened, if you live that life.”
Jorge Masvidal says the difference in lifestyle will play out badly for Conor McGregor: "It's also the lifestyle. I think Conor lives a certain lifestyle we've all seen and you can tell it's not for show and it's really his lifestyle... Max lives a completely different Show more
Conor McGregor has long become as famous for his lavish lifestyle as he is for his accomplishments inside the Octagon. From luxury cars and yachts to designer fashion, wild parties, and globe-trotting vacations, his life today looks nothing like it did when he was a hungry UFC prospect chasing greatness.
While McGregor still shares intense training footage on social media, the spotlight has often shifted toward the billionaire lifestyle he built outside fighting. And that’s where the skepticism comes in. Once an athlete becomes accustomed to that level of comfort and wealth, it becomes increasingly difficult to return to a sport where the reward for months of grueling preparation is getting punched in the face.
UFC likely offered Conor McGregor a massive payday to make the comeback worthwhile, but a lucrative contract alone doesn’t guarantee success, especially against an opponent who has stayed consistently active.
The fight is scheduled for UFC 329 on July 11, 2026, at T-Mobile Arena during International Fight Week, with the bout taking place at welterweight. To McGregor’s credit, he is currently the most drug-tested athlete on the UFC roster. Whether that preparation translates into victory, however, remains the biggest question heading into the fight.
And that’s something Chris Weidman feels is unlikely.
Chris Weidman reveals the only way Conor McGregor can beat Max Holloway
Over a month out of the fight, Conor McGregor is the betting underdog in the bout. According to BetOnline, he is a +350 underdog, and Max Holloway is a -450 favorite. And that difference in the odds also reflects in UFC legend Chris Weidman’s prediction for the bout.
“The only chance Conor really has is to knock out Max,” Weidman said. “And probably in the first or second round.”
Weidman also feels Holloway’s volume punching can land McGregor in trouble. And even the move in weight doesn’t put Weidman in doubt about the fight’s outcome.
“It is interesting with the weight difference thing, because Conor’s coming back at welterweight, but he is going against a guy who did make 145 at one point. They both fought at 55, and now at 170, so he’s not going against a true welterweight. He’s going against a guy, whatever. Max’s probably the bigger-framed guy in that fight, so that’s another thing.”
From the looks of things, Conor McGregor has an uphill battle ahead of him, at least according to the experts. And he lost three fights out of his last four. Add to that the inactivity, and there’s little chance he can pull off a win.
