#1 Jon Jones
Being the youngest champion in a sport - any sport - brings with it immeasurable baggage; just ask Mike Tyson. But it was jarring, nevertheless, when media reported that Jon Jones had crashed his $190,000 Bentley into a pole in the wee hours of May 19th, 2012. He had been crowned the youngest champion in UFC history a little over a year earlier, aged 23.
Jones was arrested on suspicion of driving while intoxicated and pleaded guilty. He avoided jail time but had his driving license suspended for six months, had to install breathalyzers (ignition interlock - a device that prevents a vehicle from starting if the driver has been drinking) in all his vehicles and was fined $1000.
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Some would call this portentous; three years later, Jones was arrested for a hit-and-run, an incident that blew the lid off his debaucherous lifestyle. His legacy in the octagon up until then was side by side with the greats of the sport. But testing positive for banned substances would leave it stained, and his redemption story was decapitated when he was stripped of the title after knocking out Daniel Cormier earlier this year. It is not known, if at all when he will return to the octagon.