7. Jack Dempsey (55-6-8, 45 KOs)
Jack Dempsey is one of the most romanticized and favorably remembered heavyweight boxing champions in history. His rise to the title is miraculous and unlikely.
There’s a logical reason why Dempsey’s early record is messy. Dempsey didn’t enter boxing in the traditional sense. He didn’t box on an amateur circuit and lacked guidance. He’s boxing’s orphan who had to do everything on his own.
Dempsey was a hobo in his mid-teens who made money by fighting on the streets. Since fighting came naturally to Dempsey, a transition to the ring made sense. He had to learn how to box on the job.
Dempsey was a brawler who had several draws and losses early in his career. He was knocked out by Fireman Jim Flynn in 1917. That fight taught Dempsey that he had to be more than a brawler, and he employed more defense from that moment. He was never knocked out again.
Under the management of ‘Doc’ Kearns, Dempsey finally found the boxing tutor he so desperately needed. Kearns helped to refine Dempsey’s fighting style and business practices.
Before winning the title, Dempsey defeated Hall-of-Famers Battling Levinsky and Billy Miske while also avenging his only KO loss to Flynn by returning the favor and stopping him in the first.
Dempsey won the title in 1919 by savagely knocking out the gigantic 6-foot-6 Jess Willard. Willard was knocked down seven times in the first round, and Dempsey stopped him in round 3. It’s rumored that Willard’s jaw was broken and several of his teeth were knocked out. The legend of Dempsey’s power caught fire after this fight.
Dempsey held the heavyweight title from 1919 to 1926. In that time he defeated Hall-of-Fame boxers Georges Carpentier and Tommy Gibbons. Dempsey was very inactive, which is why he isn’t regarded higher on this list.
He lost the last two bouts of his career against Gene Tunney who was able to out-think him in the ring, but his legacy and popularity were untarnished and are running strong.