Jake Paul's Boxing Career: 6 Key Moments Since He Joined The Sport

Jake Paul at press conference

Jake Paul has spent a decent portion of his life as an internet star and even had a brief run on television. Now he and his equally famous brother Logan Paul have gotten into boxing, and like most things they've done, made a lot of waves in the process. Love or hate them, the Paul brothers have captivated a large audience with their journey as professional boxers, though Jake's journey to being one of the most-buzzed-about fighters in the sport didn't happen overnight.

When it comes to Jake Paul, there are some key moments in his boxing career that warrant mention and help tell the story about where he's at now. Let's revisit some of those moments below, and talk about the short but major career Paul has led in the world of boxing.

Jake Paul checking his headgear

Jake Paul Takes On Deji In YouTube Throwdown

Jake Paul's boxing career essentially started over a feud between his brother Logan Paul and famous YouTuber KSI. After months of smack talk, Logan and KSI finally met in August 2018 for an amateur boxing match to decide who's tougher. KSI and Logan Paul ultimately fought to a majority draw, but the real talk of the night was the match that preceded it between his brother Jake and KSI's brother, Deji Olatunji.

Jake Paul and Deji Olatunji had a solid bout with some respectable back and forth, but Paul took over in the fifth round. Paul unleashed a mix of solid shots against Olatunji, which forced his corner to throw in the towel and award Paul the win by TKO. Following the loss, Olatunji declared that Paul failed to knock him out in the first round like he promised and said a rematch would happen. The two have yet to have that rematch, and at the moment, it's doubtful that will happen.

Jake Paul flexing during the weigh-in

Jake Paul Has His First Professional Boxing Match

A little over a year after his debut amateur match, Jake Paul successfully managed to make his professional boxing debut. Ali Loui Al-Fakhri, also known by his YouTuber name AnEsonGib, took on Paul in a match that ended relatively quickly. Paul managed to take out AnEsonGib within the first round and was awarded a win via TKO.

Critics of Jake Paul have pointed out that while this was a professional boxing match, Paul's opponent was far from the professional class. Like Paul, AnEsonGib was an amateur fighter who had his first professional fight against Paul, but unlike Paul, he hasn't had another professional fight since. Paul also had a notable height and reach advantage over his opponent, which undoubtedly played a part in his victory. While this was Paul's first professional boxing win, it was far from decisive proof for many he was a legitimate professional boxer.

Jake Paul in a wig and Nate Robinson

Jake Paul Knocks Out Nate Robinson

Jake Paul's boxing career was off to a solid start, but as previously mentioned, there were still legitimate doubts by many Paul could beat an actual professional athlete. Paul got a chance in July 2020 to make another statement with former NBA star Nate Robinson. Paul vastly outmatched Robinson in their bout and scored another win with a 2nd round knockout in a fight that wasn't even close.

Fans of Jake Paul celebrated his victory, but professionals of the boxing world shook their heads. Many were upset that the fight was even allowed to take place in a professional setting, considering Robinson had only started sparring earlier that year. Despite that, he was given a professional boxing license and could've gotten injured a lot worse against the more experienced Paul. Many professionals in the boxing industry took issue with that and pointed out that despite his skill in basketball, Robinson was still not a quality boxing opponent.

Ben Askren and Jake Paul stare down

Jake Paul Knocks Out Ben Askren

Jake Paul's next match was more or less figured out before his Nate Robinson fight, as professional MMA fighter Ben Askren heard Paul mention him in an interview and agreed to a fight. The two threw down in March 2021, and much like the Robinson fight, things ended rather quickly. Paul won the fight via TKO victory in the first round and once again proved he could beat a professional fighter with his boxing abilities.

On paper, it would be a more quality victory than the win over Nate Robinson, but even Askren admitted prior to the fight his success in Bellator MMA and ONE Championship was due to his wrestling ability. Boxing was not something he was trained for, but he felt he had a good shot at knocking out Jake Paul all the same. He found out the hard way he was wrong but still had good humor about the situation after the fact.

Tyron Woodley and Jake Paul talking

Jake Paul Beats Tyron Woodley Via Judges Decision

Jake Paul's feud with UFC Champion Tyron Woodley actually began during a verbal dispute (something common with Paul's fights) with Paul's ringside man J'Leon Love prior to Paul's fight with Ben Askren. Love teased Woodley about his lack of boxing experience, and while Woodley shrugged off the taunts by pointing out his accolades in the UFC, but after Paul knocked out Askren, Woodley called out Paul. The two then set a match to fight in May of 2021 in what would be Woodley's debut professional boxing match.

To date, Tyron Woodley has been Jake Paul's most legitimate competitor yet. Again, Woodley isn't a professional boxer with experience, but his chin and ability to throw a punch is still there. Woodley became the first opponent of Paul to make it out of the first round and delivered a shot that seemingly left Paul stunned. Ultimately Woodley lost the fight in a judges' split decision. Out of all prior challengers, Woodley is without a doubt the most notable, but again, an opponent who had little to no professional boxing experience.

Jake Paul with Irish flag and a cigar

(Image credit: via YouTube)

He Says He's On The Path To Bigger Fights, Like Conor McGregor

Jake Paul beat Tyron Woodley, but rather than back down, decided to up the ante and try for a much bigger fish in MMA. And by a big fish, we're talking about one of the biggest sports superstars of the era, Conor McGregor. Paul personally called out McGregor following his defeat of Woodley and mentioned that his star was on the rise, while McGregor seemed to be in the midst of a fall from grace.

It's antagonistic enough to warrant a response from Conor McGregor, but Jake Paul likely knows what he's doing. McGregor is known for his striking ability in the UFC, but when he was pitted against Floyd Mayweather for a major boxing event years ago, he hardly looked like a force to be reckoned with in the ring. Additionally, Paul is still the larger fighter in terms of size, so it stands to reason he could beat McGregor in a fight. That said, Paul struggled against Woodley, so there's always a chance he could poke the bear with McGregor and finally suffer his first career loss.

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Mick Joest
Content Producer

I like good television but also reality television. His day largely consists of balancing his workload between reporting on the latest and greatest news in Star Trek and other sci-fi, as well as 90 Day Fiancé, WWE, Big Brother, and more.