Unfortunately for Flair, tragedy has struck him several times regarding his children, most notably when it came to Reid. Though he showed promise in the ring in his early 20s, Reid’s career was hampered by legal issues and drug problems; between 2007 (prior to his wrestling career) and 2011, he was arrested three times, overdosed twice and, according to current WWE chief content officer Triple H, failed two drug tests that prevented Reid from signing a WWE developmental deal. On March 29, 2013, just 12 days after wrapping up a tour with All Japan Pro Wrestling, Reid died at the age of 25 as the result of an overdose. His death would have a profound effect on both Flair and Charlotte, with the latter choosing to become a wrestler in honor of her brother and to live out his dream.

Tragically struck again for Flair 11 years later, this time involving one of his stepchildren with Barlow. On October 26, 2024, Flair’s stepson, Sebastian Kidder, was found dead via self-inflicted gunshot wound. Though the cause of death was different, the situation was eerily similar to Reid’s death, as Kidder has only been 24 years old, one year younger than Flair, at the time of his passing. Flair, who had separated from Barlow only a month before, was grief-stricken, and took to social media to pay remembrance to his stepson, sharing a photo of the two together. Flair credited Kidder for being there for him, alongside Barlow and Kidder’s siblings, during Reid’s death in 2013, as well as Flair’s own near death experience back in 2017.