The 58-year-old will make his ring comeback on Friday night in Arlington, Texas, after a 19-year break, taking on YouTuber Jake Paul.
When the video-sharing website YouTube first came up in February 2005, Mike Tyson's once-intense boxing career was already teetering toward its weak end.
Four months later, the infamous "Baddest Man on the Planet," who had dominated the top heavyweights in the world in the late 1980s, was crumpling in a corner in Washington, DC, beneath the less-than-concussive fists of Irishman Kevin McBride.
The impact of those devastating early victories was lessened by Tyson's miserable professional ending, which came after countless scandals and controversies that plagued his career both inside and outside the ring.
It also called into question his hard-earned reputation as one of the most cruel and unforgiving world champions of all time.
Tyson, who has been criticized for his decision to end his 19-year hiatus from the ring and return at the age of 58, has expressed his disinterest in the concept of a legacy.
In a conversation with Interview Magazine, Tyson explained that he never knew what a legacy was and that he will be dead soon, so who cares about what people think about him when he's dead? This statement is fitting given the nature of Friday's upcoming event, which was founded by Andy Warhol in 1969.
Tyson, the youngest world heavyweight champion in history, has endured countless hours in the spotlight since his debut in 1986. His latest bout, scheduled for Friday, will feature eight two-minute rounds using 14oz gloves.
Tyson has also turned his autobiography, 'Undisputed Truth', into a one-man stage show and made cameo appearances as a pantomime version in professional wrestling shows.
He claims to have found spiritual enlightenment by smoking toad venom, despite his past struggles, including a rape conviction and bankruptcy. The bout is the latest chapter in Tyson's journey to a place of relative calm in late middle-age.
Tyson stated, "I tried this spiritual medicine called the toad." It becomes difficult when you see a toad, break its puss, and put it on like a mirror.
You smoke it after rubbing it down till it becomes like fine sand. After that, you encounter God. And God instructed me to do this.
Paul Tyson, a YouTuber with 70 million fans, is expected to dominate a multi-million TV audience.
Born five months before his 1997 'Bite Fight' loss to Evander Holyfield, Tyson believes Paul should have been chosen as the ultimate reality TV foe.
Tyson believes Paul's immense fan base and his status as the greatest fighter in history create an explosion of excitement, highlighting the importance of making the biggest impact before one's death.
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