5 times Jake Paul brutally insulted Conor McGregor feat. $50 million fight offer rant

Jake Paul has long been at loggerheads with Conor McGregor. Their rivalry is believed to have commenced with the YouTuber repeatedly jibing at McGregor, whereas the legendary MMA fighter would seldom acknowledge him.

In recent years, Paul has emerged as a prominent attraction in boxing and combat sports overall. Nevertheless, he's also oft-criticized for not facing full-time boxers and primarily boxing against MMA fighters or considerably older athletes. The 27-year-old last outpointed 58-year-old Mike Tyson in November 2024.

Meanwhile, Conor McGregor hasn't partaken in an MMA bout or any other professional combat sport contest since July 2021. McGregor recently tweeted he could face Logan Paul, Jake's older brother, in an exhibition boxing match organized by the Ambani Family in India in 2025.

Moreover, reports suggest McGregor could instead box against Jake Paul. In November, Paul himself called out McGregor, who's currently under contract with the UFC MMA organization, for an openweight MMA fight. But experts deem that unlikely.

However, McGregor's possible exhibition boxing match, especially with the Ambani Family supporting it, has been deemed as something the UFC could consider. In the wake of the Conor-Logan and Conor-Jake boxing rumors, we revisit Jake's long-running animosity against the Irishman -- looking at some instances when 'The Problem Child' brutally insulted the UFC legend.

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#5 Jake Paul's $50 million fight offer rant

Jake Paul's professional boxing debut transpired in January 2020. Later that year, he pitched a $50 million offer for McGregor to box against him. Calling out the ex-UFC featherweight and lightweight champion, he even jibed at the Irishman's longtime partner, his fiancé and the mother of his children Dee Devlin. Also seemingly jabbing at Ireland, with an Irish flag wrapped around him, Paul stated:

"What the f**k is up, you Irish cu*t? Good morning, Conor McGregor. I know you're probably beating up old dudes in a bar right now, or maybe you're ja*king off because you're sick of f**king your wife. I mean, she's a four, Conor. You could do a lot better. But happy Monday.

"My team sent you a 50 million-dollar offer this morning. 50 million dollars cash, proof of funds. The biggest fight offer you've ever been offered. But you're scared to fight me, Conor. You're ducking me because you don't want to lose to a f**king YouTuber."

Paul referenced his supposed pay-per-view success and alluded to McGregor's lightweight MMA bout against Dustin Poirier that was booked for January 2021. Labeling him "Dustin Prober," he discredited Poirier as someone with a negligible fan following.

He also hurled epithets at then-UFC president (now-UFC president and CEO) Dana White, whom he's still at odds with. Paul added:

"Conor, you scared. Dana, you're scared. Sign the f**king contract, you idiots ... Irish bi*ch. F**k these guys."

Paul later attempted to justify his hurling insults against Devlin, citing that McGregor previously made questionable remarks regarding Khabib Nurmagomedov's wife. Regardless, many fans condemned Paul for his remarks. Well, on Logan Paul's Impaulsive podcast in 2023, Jake claimed he'd grown up and wouldn't mention people's partners/wives in his trash talk battles anymore.

Watch Jake Paul's infamous $50 million rant from 2020 below:

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#4 Jake Paul's insulting offer after Conor McGregor's first MMA knockout defeat

Jake Paul consistently accused Conor McGregor of evading a fight against him. McGregor fought Poirier at UFC 257 in January 2021 and was stopped via second-round TKO. The Irishman had previously beaten Poirier via first-round TKO at UFC 178 in September 2014, and many viewed his knockout loss in the rematch as an upset.

It also marked the first time McGregor had lost via KO/TKO in the sport of MMA. His only other KO/TKO loss in combat sports overall was a TKO loss against Floyd Mayweather Jr. in his lone boxing match in 2017.

Speculation abounded that the UFC 257 loss dented McGregor's brand value. Jake Paul then tweeted a video of himself mocking McGregor, beratingly offering him $10k rather than $50 million:

"AYE @thenotoriousmma INSTEAD OF $50 MILLION I GOT $10,000 for you now CASH THO!! ALL CASH"

Watch Paul sound off on McGregor below:

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#3 Jake Paul's $23 offer, infamous 'Sleepy McGregor' chain exchange with Dustin Poirier

Many in the MMA and broader pop culture realms stood witness to a major shift in Jake Paul's approach toward Conor McGregor through 2021. Though initially dismissive of Dustin Poirier, Paul soon realized that he'd be better off joining forces with him against McGregor.

McGregor was incredibly respectful toward Poirier heading into UFC 257, which was in stark contrast to his unrelenting trash talk against the American before their first fight in 2014.

After getting knocked out in the rematch, McGregor's trash-talking persona returned. He directed fiery insults at Dustin and his wife Jolie Poirier -- with both fighters even trading accusations of donation promises being unfulfilled.

Meanwhile, Jake Paul unraveled a 'Sleepy McGregor' chain/necklace, depicting McGrgor's knockout defeat. Claiming that it was worth $100k, Paul posted it all over his social media. After McGregor suffered a gruesome mid-fight leg injury and lost to Poirier via first-round TKO in their trilogy fight at UFC 264 in July 2021, Paul mockingly offered McGregor a $23 payout for a possible fight against him.

Additionally, Paul sent the 'Sleepy McGregor' chain to Dustin, with a respectful note to him and Jolie. Dustin later tweeted he'd auction the chain and donate its proceeds to his Good Fight Foundation.

Check out the chain below:

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#2 Jake Paul's rehab jibe and downplaying potential Conor McGregor fight

Jake Paul defeated MMA legend Nate Diaz via unanimous decision in their boxing match in August 2023. Many fight fans criticized Paul for facing Diaz, who generally fights in a much lighter weight class, that too in the sport of boxing. Paul claimed he'd rematch Diaz, who's 1-1 with McGregor in the sport of MMA, in MMA under the PFL promotional banner.

Between the 2021 and 2024 timeframe, a key evolution in Paul's insults against McGregor was that he gradually began downplaying the Irishman's value as a worthy opponent.

During his post-fight press conference after beating Diaz, Paul appeared to discredit Conor McGregor. Paul -- who's consistently issued call-outs to McGregor, whilst simultaneously claiming he isn't a deserving opponent -- jibed at McGregor's alleged substance abuse issues:

"I don't care about that guy [McGregor]. He needs to go to rehab. I want Nate in MMA. I want more professional boxers, and I want Canelo [Alvarez]."

Watch Paul discredit McGregor below (4:00):

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#1 Jake Paul's response to Conor McGregor on Mike Tyson fight, cocaine allegations and MMA rant

During a DuelBits livestream earlier this year, Conor McGregor sounded off on many of his rivals, while seemingly smoking and consuming alcoholic beverages. The video went viral, with some praising the Dubliner for his entertaining persona and others criticizing the smoking and drinking aspects.

Jake Paul later posted a video to his official YouTube channel, featuring snippets from McGregor's stream and his own impersonation of the Irishman. Also, many fans opined that the white powder Paul donned on his face was a reaffirmation of the cocaine use allegations he's time and again levied against 'The Notorious.'

Watch Paul impersonate McGregor below:

Prior to Jake Paul's boxing match against ex-UFC welterweight and BKFC staple Mike Perry in July 2024, BKFC co-owner Conor McGregor deemed Paul a "little dweeb." McGregor asserted that Perry would likely put the YouTuber away. During their pre-fight press conference, Paul went on a fiery expletive-laden rant against Perry, McGregor, and other MMA fighters:

"Your words as MMA fighters are f**king meaningless ... Every single MMA fighter is a f**king pu**y, and you can't box for sh**. And when I try to fight y'all in MMA, y'all don't do it ... Pu**ies. You and McGregor, both bi*ches, will never fight me. F**king pu**ies."

Check out Paul's rant below (13:09):