Brailey toured the UK and France at the end of 2014 as a member of the Australian Schoolboy team. Having been a local junior at the Aquinas Colts club, Brailey came through the Sharks Academy and Junior rep system, playing for the Sharks NYC team in 2015 and 2016. He won the 2016 Dally M Holden Cup under-20s player of the year. In 2017 he debuted with the Sharks. Brailey performed outstandingly as the Sharks hooker and played in the 2018 preliminary final. In 2019 Brailey signed up for a three-year contract with the Newcastle Knights.