May 29, 2026 — 3:30pmTwo years ago, Scots College student Harry Kyle emailed the Sydney Swans academy, speculatively requesting a try-out.Kyle politely acknowledged his experience in Australian rules was limited, but pointed out that he had excelled at basketball and rugby at school and felt his skills might be transferable.Sydney Swans captain Callum Mills congratulates Harry Kyle on his debut. Mills and Kyle both grew up playing rugby in Sydney before switching to AFL.Phil HillyardHis hunch was correct. Within a year, he was selected in the first round of the AFL draft, and on Saturday Kyle will make his debut for the Swans against Richmond at the SCG, replacing injured club captain Callum Mills.Former Swans player Colin O’Riordan was academy coach at the time, and the man who opened the email from the Sydney schoolboy who fancied a crack at the AFL. O’Riordan and his team had received numerous requests from interested athletes before, but Kyle’s sporting background stood out. He was given a four-week trial with no guarantee of anything beyond it.“For his first training session, he was raw as hell, but you just could tell from the second he came in, this kid can play,” O’Riordan said.“His spatial awareness, his footwork, the way he moved was very [Giants midfielder] Finn Callaghan-like, to be honest.“You just could tell from the second he came in, this kid can play.”Former Swans academy coach Colin O’Riordan“I’m always cautious comparing kids to great players, but he moves in such a way that he could see the game really well for someone who hadn’t played it very long. And then that weekend, we had no option but to play him – we knew, you’ve got to play this kid straight away.”Kyle had dabbled in Australian rules as a junior with the Willoughby Wildcats, but there were too many sports that he wanted to play and not enough time to fit them all in.He excelled at soccer, basketball, rugby and swimming. But it was a GPS athletics carnival in September that stood out for Graham Pattison, the deputy principal, sport and co-curricular at Scots.“Harry was so busy with his other sport commitments that he didn’t train all too much for athletics, but he came out on the day and he won the open high jump at the GPS Athletics Championship and jumped two metres,” Pattison said.“He just turned up and jumped like that. I haven’t seen too many kids be able to do that sort of thing or have that type of athletic ability.”Though he continued to impress at the Swans academy, Kyle needed exposure to senior football and began playing for UNSW Eastern Suburbs Bulldogs, the former club of Swans Errol Gulden, Braeden Campbell and another late convert from basketball, Dane Rampe.UNSW president Iain Dunstan has been involved with the club for 18 years, but cannot remember a player who has excelled so quickly at the game – almost from a standing start.“I’ve never seen anyone be that good off so few games,” Dunstan said. “He picked up the ball off the halfback flank and had four bounces and kicked the goal from, like, 55 metres out in his first or second game.Harry Kyle was drafted with pick 14 in the AFL draft in 2025.Phil Hillyard“I turned to Robbie Chancellor, who was our coach, I just went, ‘Well, he just went up 20 draft places’.”Chancellor was proven correct. In November, Kyle was picked at No.14 in the AFL draft, a surprise to everyone except those who had worked with him over the last two years in Sydney.At the Swans academy, O’Riordan describes Kyle affectionately as “a silent assassin” who was desperate for feedback, regardless of how brutal, such was his desire to improve.There is a sense of irony in the fact that Kyle replaces Mills on Saturday. Mills was also an early rugby union standout from the north shore, before switching to Australian rules.O’Riordan realises Kyle is filling big boots, but has every confidence the young man who once sent a hopeful email can continue his upward trajectory in the AFL.“The biggest thing for him, I think, is enjoying the moment. He’s clearly going to be nervous, and that’s the danger of playing in front of 40,000 people on a Saturday afternoon,” O’Riordan said.“But you get one opportunity to debut, and you need to enjoy it. Nerves are normal. If you weren’t nervous, it means you don’t care, and Harry cares a lot.”News, results and expert analysis from the weekend of sport sent every Monday. Sign up for our Sport newsletter.From our partners