Early on, it seemed as though coaching was the more likely future for Connor than playing at an elite level. He was a late bloomer, undersized when he was eligible for the OHL draft. He was essentially an afterthought, going 251st to the Erie Otters in 2010. He spent the next season playing for the St. Michael’s Buzzers in the Ontario Junior Hockey League, before joining the Otters for the 2011-12 campaign. The late selection and year of seasoning didn’t discourage Brown. In his first season, he led the Otters in scoring with 25 goals and 53 points, but the team finished last in the league with just 10 wins.

That June, the Brown family sat in their living room watching the NHL Draft as it unfolded in Pittsburgh. While there was hope that Connor would be picked, there wasn’t enough assurance for the family to attend in person. They sat nervously as several of Brown’s former minor hockey teammates and good friends were selected. In the sixth round, the Maple Leafs called Connor’s name—156th overall. The number had significance for the family. It was the lucky number of Anne’s late father, Tom Kennedy, who grew up at 156 Greenlaw Ave. in Toronto and always boxed the numbers when he gambled at Woodbine Racetrack. “It’s like a dream,” says Anne Brown. “I don’t think it’s fully registered.”

Still, Brown was a long way from actually getting on NHL ice. He was named captain of the Otters when he returned in 2012-13. That season, a 15-year-old rookie named Connor McDavid joined the team. The following year, Brown broke out on a line with McDavid and Dane Fox, netting 45 goals and 128 points in 68 games to lead the OHL in scoring. But even through his remarkable offensive campaign, his coach, Kris Knoblauch, was just as impressed with what Brown did on defence. “If someone stole the puck from him, he’d almost take it personal. We used to joke that on our five-on-three kill we didn’t have a system—we just had [Brown],” Knoblauch says. “He would break up every single play … It’s not often you see a guy win a scoring title. But I was more impressed with his defensive play.”