When you beat a legend, you become a legend. Jake Paul was already a legend—not just because he is the brother of Logan Paul, also a humble legend. With a net worth way over hundreds of millions of pesos, an internet following in the tens of millions, and a near-perfect boxing record, Jake Paul was set to become a sensation. After a convincing, non-scripted victory over ‘Iron’ Mike Tyson, ending his near 20-year undefeated streak, Jake Paul cemented himself as not only the baddest man on the planet, but also as the face of boxing. But how does he stack up against the former greats, and could they live with Jake Paul in this modern era of boxing?

Jake Paul's Boxing Legacy in the Modern Era

1) The Galveston Giant – Jack Johnson

Jack Johnson (6 feet, 200 pounds, 74-inch reach) was a champion who reigned supreme, defeating Tommy Burns in 1908 to capture the belt. He held the title for seven years and lived an extraordinary celebrity lifestyle, making him an awesome chap well worth reading up on. He even punched out middleweight champion Stanley Ketchel’s teeth, showcasing his power.However, Jake Paul has a granite chin, as demonstrated in the Tyson fight—even when Paul’s chin was open, Tyson dared not hit it for fear of breaking his hand. Jack Johnson was actually shorter than Jake Paul, had a smaller reach, and weighed less. It’s tough to imagine the conditions they had to train in and endure 100 years ago. There was no internet or mobile phones, so you couldn’t constantly take photos and videos for social media, which might make Jake Paul feel bored from not getting enough attention and lose motivation to train. But these fights are taking place in the modern era, and given the physical advantages Jake Paul has, it is hard to see anything other than a win for Jake Paul, perhaps even getting a late stoppage after Jack Johnson has hurt his hands on the baddest man on the planet’s face.

2) Jack Dempsey – The Manassa Mauler

Jack Dempsey (6 feet 1 inch, 187 pounds, 74-inch reach) is a renowned figure in boxing history, known for his incredible punching power, popularity, and being the first fighter to achieve a million-dollar gate. He had a ferocious style and defeated Jess Willard, who was massive, to become the heavyweight champion in 1919.The technology for training back in the 1920s wasn’t like today’s air-conditioned gyms with advanced equipment and machines. Jake Paul would likely struggle with the lack of modern training methods, making it understandable that a fight in those conditions would never take place, and he might not achieve the same level of fame as he has today as there was no YouTube. In fact, in those days, he might even get spat on for being so out of place.In today’s modern era, with all the privileges he has, Jake Paul holds a significant weight and reach advantage, along with the new rules of boxing. Even if he could get knocked down (which he can’t, as his chin is granite), Jack Dempsey would have to stand in a neutral corner, just as he did in the Tunney rematch where he lost. Dempsey was also knocked out previously, and Jake Paul punches super hard (according to himself), so he would likely defeat Jack Dempsey convincingly with a knockout victory.

3) Joe Louis – The Brown Bomber

For many boxing enthusiasts, Joe Louis (6 feet 1.5 inches, 200 pounds, 76-inch reach) is considered the best heavyweight to ever win the title, holding it for over a decade. His combination of power, speed, and footwork has left many fans in awe, and some believe he would even be a champion in today’s climate. He had a remarkable career but sadly had to make a comeback due to financial reasons. It is said that the IRS kept going after him for monies owed on a charity donation, leading to his matchup with Rocky Marciano, which was to be his last.A prime Joe Louis would have given Jake Paul little trouble, as Jake Paul has hand speed that surely outmatches that of Joe Louis, along with a massive weight and reach advantage. The only real advantage Joe Louis has, apart from being a legitimate all-time great heavyweight champion, is his combination punches. Many have questioned Jake’s stamina to go the distance, but after watching him go a full 16 minutes with a 58-year-old Mike Tyson, I don’t think anyone can legitimately question his stamina.Jake Paul doesn’t really throw combinations, as he is so heavy-handed that a jab can do the work of ten punches from someone like Joe Louis. So potentially, Joe could get a few rounds in the bag with a higher punch output. However, it is more likely that Jake Paul would box on the outside, keep Louis befuddled with his master tactics, and wear down the former champion. A knockout win similar to what Marciano achieved would surely be the outcome.

4) Rocky Marciano – The Brockton Blockbuster

Rocky Marciano (5 feet 10 inches, 185 pounds, 68-inch reach) is the only heavyweight champion to retire undefeated, and alongside Lennox Lewis, the only champion to retire as a champion. He was absolutely brutal, with unprecedented punch power and all-out, non-stop punching. His ability to endure tough fights, cut off the ring, land his shots, and get up off the canvas made him a formidable opponent back in the 50s. He boxed older legends such as Louis, Walcott, and Moore, something Jake Paul is adept at doing.Back in those days, with the much smaller gloves they used (literally half the size of the ones Jake Paul used against Mike Tyson), the punches would have had more devastating effects. It really was a much more brutal sport then. It is hard to fathom just how much more damage a monstrous puncher like Jake Paul would dish out, especially against the smaller Marciano. But since we are boxing in today’s era, the gloves would be larger. Perhaps even against Marciano, Jake could get him to wear 20 oz or larger gloves, to save Marciano’s hands from instantly breaking on Jake’s strong chin. Either way, Jake is just far too big, strong, and powerful for Marciano to overcome, although with his heart, he would likely see out the final bell, feeling proud to have gone 8 x 2-minute rounds with the GOAT.

5) Sonny Liston – The Big Bear

Like Marciano before him, Sonny Liston (6 feet 1 inch, 220 pounds, 84-inch reach) had mob connections, was said to be an enforcer and debt collector, and was feared both in and out of the ring as someone you did not want to cross. He even fired a blank at Ali in a casino from his handgun—a stunt only a fellow legend like Jake Paul would dare to do.Liston is the first on this list to match the physical size of Jake Paul, even surpassing him in reach. Known for his massive fist size and wrist, indicating thick, dense bones and strength you don’t get from pumping iron, Liston sure looks like a worthy opponent for Jake Paul. However, like Mike Tyson, Sonny Liston is often considered a bit of a hype job. He won the title by smashing Floyd Patterson (trained by Cus D’Amato) and defended it once, also against Floyd, before being beaten by Ali (then Cassius Clay).While you can watch footage of Sonny Liston, such as his 1959 fight against Cleveland Williams, and admire his heavy, long, hard jab—one of the best ever—you might think he would easily beat up Jake Paul. But there are several things to consider. First, Liston died at age 40, which means he didn’t live long enough to be a likely opponent for GOAT Jake Paul. Second, Jake Paul is the “problem child” who defeated Mike Tyson. Even if Liston could get close, Jake has the power to fend off ferocious attacks just by whispering in an opponent’s ear. Don’t forget, this ability is his own fear factor. I’d imagine the matchup, set in the modern day, would look something like the rematch Liston had with Ali—Paul KO 1.