Conor McGregor returns against Max Holloway after nine-year spiral

Conor McGregor will return to the octagon against Max Holloway at UFC 329 on July 11 in Las Vegas, the promotion announced this week, closing a chapter that began with a guaranteed $30 million payday and spiraled into arrests, injuries, and multiple sexual assault allegations.

The fight marks McGregor's first appearance since his last UFC win — a span ESPN traced back to the 2017 Floyd Mayweather boxing match that netted the Irishman a disclosed purse north of $100 million when factoring pay-per-view, gate, and sponsorship revenue. That windfall, which followed a career-high $6.8 million for beating Eddie Alvarez at lightweight, changed McGregor's trajectory immediately. "Conor might never fight again," UFC president Dana White told reporters at a media luncheon that November, per the ESPN retrospective. "The guy's got $100 f---ing million. Try to get up every day and get punched in the face when you have $100 million in the bank. Money changes everything."

From Mayweather spectacle to criminal charges

What followed was one UFC victory and a documented free fall: a November 2017 Bellator cage invasion, the March 2018 stripping of his lightweight title due to inactivity, and the infamous April 2018 dolly attack at Barclays Center that injured three fighters and led to assault charges. McGregor turned himself in to the NYPD after hurling a metal dolly at a bus carrying Khabib Nurmagomedov, shattering a window. White called it "the most disgusting thing that has ever happened in the history of the company."

Combat photographer Esther Lin, who documented the Mayweather-McGregor world tour, told ESPN she saw the shift in real time during the Toronto stop. "Conor was realizing that he was just as popular as Mayweather and he could have his audience," Lin said. "He certainly embraced it during the tour and knew exactly how to ride that to the top." The three-piece suit gave way to floral pants and a mink polar bear coat. Friendly banter turned into racially insensitive jabs.

McGregor went on to lose to Nurmagomedov at UFC 229 in October 2018, then dropped two of three against Dustin Poirier, including a broken leg that sidelined him for over a year. The July 11 bout against Holloway — whom McGregor beat in 2013 on a $24,000 disclosed purse — closes the loop on a rivalry that predates the money.

Source: espn.com