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Much like his cousins, Ron Bailey was a stand-out football player in high school, both as a hard hitting free safety and as a tight end. Unlike Champ Bailey and Boss Bailey, however, Ron's path didn't lead him to play football at the collegiate or professional level. After being introduced to the world of sports betting at a local barbershop in his hometown, Ron entered the world of monitary risk taking and never looked back.

In one of his many trips to Las Vegas, Ron Bailey got introduced to some men who were involved in mixed martial arts training. After watching a couple of pay per views, he wanted to be trained. Although he never got the chance to fight on one of those pay per views, many consider him to have enough talent to be signed by any of the major MMA promotions in either the United States or over in Asia.

Following the money and the potential for greater career longevity, Ron Bailey decided to enter the world of professional wrestling, making LEGACY his first (and thus far only) stop. Although he doesn't bet on his own matches, his penchant for betting on other people's matches and desire to gain an inside edge in those matches has already blown up in his face... but it has also earned him quite a bit of money on top of his salary.