Early Life and Junior Football
Born to Cyril Jr. and Kathy in 1989, Rioli was introduced into a bloodline of talented footballers. His grandfather Cyril Sr. fathered Cyril Jr., who was a champion footballer in the Northern Territory and his brother, Richmond Norm Smith Medallist Maurice Rioli. Cyril Jr. played for Northern Territory Football League club St Marys, where he won 12 premiership medallions and the 1995–96 Nichols Medal as the league's best and fairest player. His mother Kathy is two-time premiership player and 1993 Norm Smith Medallist Michael Long's sister. Rioli has a sister named Kalisha and another former footballer, Dean Rioli, is his cousin. He spent the first eight years of his life in the Tiwi Islands before moving with his family to Darwin in the Northern Territory, playing his younger years at St Marys also.
Rioli moved to Melbourne in 2004 as a 14 year old, where he attended and boarded at Scotch College for four years whilst playing for the school's football team. The move came about after a decade-long relationship between the school and Indigenous communities of the Northern Territory. Dr. Rob Smith, a teacher at Scotch College, had expanded the school's four-week exchange program for talented Indigenous footballers into a full scholarship program, following numerous tours of the Tiwi Islands and specifically, Bathurst Island. Rioli was the first selected into the program. He originally made the trip alongside his cousin Steven, after just three days in Melbourne the two re-packed their bags with the intention of returning home. In an effort to retain the boys, Smith phoned Michael Long, who came out to the school with Derek Kickett and Sibby Rioli, another uncle. Long said he knew Cyril was making a life-defining choice at just 14; "That was the big moment, whether he'd tough it out or go". Steven returned home and Cyril persisted in Melbourne. Nicknamed "Junior" or "Junior Boy", he shone in his final season with Scotch College, despite suffering injuries throughout the season; including a broken collarbone and a severely damaged ankle. He developed somewhat of a cult following whilst playing for the school, following a video clip of his highlights being uploaded to YouTube. He has since stated that he believes the early move to school in Melbourne made the transition a lot easier.
Rioli was also a standout performer in the 2007 AFL national under 18 championships, becoming the only Northern Territorian to earn All-Australian honours, following a seven-goal performance in a match against Queensland. He was tipped to go high in the national draft, from anywhere between five and twenty-five. In this final year of junior football, he was one of five players, including Trent Cotchin, to be chronicled in the book The Draft: Inside the AFL's Search for Talent, by The Age journalist Emma Quayle.
Despite Rioli's speed, evasiveness and flashy tricks, the scouts at the AFL's draft camp were still to be convinced of his dedication, with his skin folds being described as "less than brilliant" and his commitment to AFL still being questionable. Prior to the draft, Rioli said "I have had a few clubs call me, and it's just confusing. I love playing footy, and I think I am pretty good at it, but it doesn't really matter where (I go in the draft)." He reportedly spoke to both the Kangaroos and the Adelaide Crows, before eventually being drafted by the Hawthorn Football Club in the 2007 AFL Draft. The Hawks used their first-round draft pick and the number 12 pick overall to claim Rioli.
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