#4 His number of marriages
One could say that Flair's life was certainly a study in life imitating his character's art. The 'Nature Boy' persona was that of a man who dressed in the finest clothes, rode in the most expensive cars and limos and was a ladies' man.
Before that persona was really associated with Flair, he married his first wife, Leslie Goodman, in 1971. They would have two children, David and Megan, but divorced 12 years later in 1983.
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He would marry his second wife, Elizabeth Harrell, in August of 1983. With Harrell, he would have children Reid and Ashley (Charlotte). The couple was together until they divorced in 2006 after 23 years together.
Later in 2006, he would marry his third wife, Tiffany VanDenmark, but the two would divorce in 2008. In 2009, he married his fourth wife, Jackie Beems but the two divorced in 2012.
He later married his fifth wife, the former 'Fifi the Maid' in WCW, in September of 2018. Who really knows why he was married and divorced so many times in his life. Maybe it was his persona taking control outside of the ring or maybe he jumped into the marriages too prematurely.
Getting married again so soon after divorcing probably didn't help things, but a psychologist might think that those were the actions of someone who didn't like to be alone.
He was either married in the same year he divorced a wife or a year later four times. Since he was adopted, perhaps he understandably had some issues with abandonment. While we will never quite know for sure, he loves his kids and they obviously love him.
David had a run in WCW in the late 1990s but was never above the midcard. Charlotte is obviously much more talented than David, having already been a women's champion seven times in the WWE.
And his son Reid was an amateur wrestler who had signed a WWE Developmental deal in 2007.