UFC 330: Ian Machado Garry's Eddie Hearn gamble comes to a head

Ian Machado Garry pulled off a shrewd piece of timing by securing his UFC 330 title shot against Islam Makhachev before revealing his partnership with Matchroom Talent Agency.

Two months before his showdown with the pound-for-pound best fighter in the world, Garry's partnership with Dana White's most formidable opponent in many years, Eddie Hearn, was made public. 

Matchroom Talent Agency's first signing was Tom Aspinall, the UFC heavyweight champion who found himself on the wrong side of White's favor in the aftermath of UFC 321. Hearn admitted that he may not have pursued managing Aspinall's commercial interests had it not been for White's Zuffa Boxing signing one of Hearn's key Matchroom talents, Conor Benn.

Since signing Aspinall, Hearn has used the conditions of the heavyweight champ's contract as a stick to beat the UFC CEO with. The back-and-forth between the figureheads has become one of the most intriguing talking points in combat sports. 

For those unfamiliar with Garry, he has never shied away from patting himself on the back. As well as celebrating his own ability, he has endlessly praised the work of the team around him for building his brand. 

Yet, when it came to sharing his thoughts on the Matchroom partnership — the most publicized deal of his career outside of his UFC signing — "The Future" appeared to be suddenly aware of how his collaboration with Hearn could muddy the waters with him and his UFC paymasters. In an appearance on "The Ariel Helwani Show," he went out of his way to underline that his Matchroom signing would have no impact on his dealing with White and Co. 

"This signing has nothing to do with the UFC, it has nothing to do with my job inside the Octagon," Garry told Helwani on the day of the announcement. "It has everything to do with what's happening outside of the Octagon. 

"I believe that Eddie can help me build my brand outside, so I can have more eyes in the Octagon. … All of this is tactical, all of this is calculated and all of this is planned," Garry added. 

Given White's dismissal of Aspinall's willingness to continue at UFC 321 and downplaying his injuries, the link-up with Hearn wasn't all that surprising. Garry, on the other hand, felt as though he had a comparative promotional rocket strapped to his back since signing for the promotion in 2021. 

"The Future" debuted at Madison Square Garden at a pay-per-view event. After his first-round dispatch of Jordan Williams, he declared himself the second coming of his countryman and inspiration, Conor McGregor, and insisted he would usher in "the Irish Invasion, Part 2" — a sequel to the halcyon days of McGregor. 

While some fighters can be put behind the eight ball in terms of championship trajectories, the UFC has granted the Irish welterweight opportunities to put himself in the title mix by booking him against the likes of Shavkat Rakhmonov and, later, Belal Muhammad. 

Garry, to his credit, has been a company man, too. He accepted short notice replacements when Geoff Neal and Joaquin Buckley withdrew from their dates with him. He also stepped up to fight one of the boogeymen of the division, Carlos Prates, at the 11th hour. Then he went on to claim arguably the biggest victory of his organizational tenure. 

Being booked to fight Makhachev, who’s making his first welterweight title defense, is proof of Garry’s standing with the promotion. Although many saw him as the rightful top contender, Prates and Michael Morales became the sexy picks with their heroics at UFC 322, where they banked massive wins over Leon Edwards and Sean Brady, respectively. 

Although he believes his task is the toughest a challenger has ever faced, Garry also believes he will finish the greatest fighter on the planet when they meet in Philadelphia on Saturday night. 

However, should he come up short, the new reality of the post-Hearn era could be revealed to all. 

While Garry has proved his worth as an elite fighter, his aspirations to compel the Irish to another invasion have not come to fruition. As he and Hearn admitted, part of his reasoning for signing with Matchroom was to make him a bigger deal back home. 

Initially, things have gone well. Speaking to those who attended his unveiling press conference in Dublin last month, about a hundred people waited around to meet the hometown hero after he finished his media obligations. Irish media outlets had seemed unimpressed by Garry’s early run in the UFC, but Hearn’s involvement appeared to bring with it some renewed attention from the local press.

We are entering a very intriguing time for Hearn's talent agency. The white smoke from Atherton suggests Aspinall is ready to fight. Yet, according to Helwani, even though a rematch with Ciryl Gane seems like an open goal for Abu Dhabi in October, the powers that be might find motivations not to give it the green light — one of them likely being Aspinall's relationship with Hearn. 

"I think games will be played," Helwani said on a recent episode of "The Ariel Helwani Show."

"I think [the UFC] know he wants to come back and they're going to say, 'Sit right there, we're going to tell you when we're ready for you,' and then they're going to drag this out as long as possible." 

Who knows if Garry would've been granted the biggest fight of his career had his Hearn signing went public before the UFC 330 main event was made official. 

If he manages to upset the apple cart, break Makhachev's 16-fight winning streak and become the first man to defeat the champ since his sole loss in 2015, Garry will still have leverage and will likely owe the two-weight division champion an immediate rematch. The UFC's feelings on his dealings with Hearn will become much clearer if he suffers the widely predicted defeat to the Dagestani champ. 

Let's just hope everything has been as "tactical," "calculated" and "planned" as Garry claimed it was. Because, for a fighter who has been shown relative favor in how he's been handled up until this point, the reality of winning the ire of the promotion could hit like a hammer in the aftermath of a defeat at UFC 330.