Brew has won the Bruce Montgomery Trophy as Werribee's best-and-fairest player on three occasions and was awarded the Nichols Medal while playing for Nightcliff in the Northern Territory Football League (NTFL) during the 2020–21 season. He is the only player to have won both the J. J. Liston Trophy and the Nichols Medal as the best-and-fairest player in the VFL and the NTFL respectively.
As of 2026[update], Brew has played the second-most matches for Werribee in the history of the club, only behind Robbie Castello.
Career
Brew made his debut for the Albury Football Club in the Ovens & Murray Football Netball League (OMFNL) in 2014, playing in the reserves and thirds competitions. He made his senior debut in 2015 and played three matches but was not selected in Albury's senior team that won the OMFNL grand final, instead playing for the reserves team in a preliminary final loss to Wodonga.
Werribee officially signed Brew to the club's Victorian Football League (VFL) playing list for the 2017 season. He played in the Development League until making his senior VFL debut for Werribee against the Northern Blues in round 9, recording twenty-two disposals and seven tackles in a 14-point victory. Brew remained at Werribee in 2018 and 2019 after the club returned to competing as a standalone team following the end of its reserves affiliation with North Melbourne.
On 10 March 2022, Brew was appointed Werribee co-captain, serving alongside Tom Gribble. He stepped down from the role before the start of the 2023 season but was appointed as a co-vice-captain with Shaun Mannagh. After playing all 21 VFL matches in 2023, including Werribee's grand final loss to Gold Coast, Brew was named in the VFL Team of the Year and won the Bruce Montgomery Trophy as Werribee's best-and-fairest player. In 2024, Brew had his best season to date, captaining the VFL in an interstate match against the South Australian National Football League (SANFL) and averaging 28.8 disposals during the home-and-away season. He won the J. J. Liston Trophy with 31 votes – the second-highest total under the 3–2–1 voting system – in addition to being named captain of the Team of the Year, winning the VFL Coaches MVP Award and claiming a second Bruce Montgomery Trophy. Because Nick Coughlan was injured, Brew served as Werribee's acting captain for the 2024 grand final, which the club won by six points to end a 31-year premiership drought; Brew was in tears during a post-match interview.
Following his successful VFL season, Brew was invited by the Western Bulldogs to train ahead of the 2025 AFL season, with the possibility of gaining a spot on the club's Australian Football League (AFL) list. He played for the Bulldogs in a preseason match simulation against Essendon, but was ultimately not chosen to join the club. Brew remained at Werribee for the 2025 VFL season, played in a second representative match against the SANFL and was named in the VFL Team of the Year. He won the Bruce Montgomery Trophy for a third consecutive season, becoming the third player in Werribee's history to achieve the feat (after Travis Robertson and Matt Hanson).
↑"2016 VAFA Annual Report". VAFA. 5 December 2016. p.43. Archived from the original on 7 July 2025. Retrieved 6 November 2026. Best Players: D. Smith (Peter Knights Medal), D. McMahon, D. Brew, T. Hanna, S. Dunstan, J. Kelly