Countdown to Round 1, 2026. Day 27: Essendon Guernsey Number 27

Don TheStat
4 hours ago
2 min read

With 27 days to go until Essendon’s Round 1 clash with Hawthorn, Don The Stat continues its daily countdown through Essendon’s guernsey history.

Guernsey Number 27 stands as one of the most iconic numbers in Essendon history, worn by Premiership players across multiple eras and defined by one of the greatest individual careers the club has seen.

The number was first worn by Frank Caine in 1912–1913, across 17 games. Caine was a member of Essendon’s 1912 Premiership side, giving the jumper an early place in club success.

After passing through several hands in the first half of the 20th century, Guernsey Number 27 entered its most significant chapter in 1974, when Simon Madden debuted wearing the jumper. Madden wore #27 from 1974 to 1992, playing 378 games and kicking 575 goals. He was a key member of Essendon’s 1984 and 1985 Premiership teams, and holds the record for most games and most goals ever recorded in Guernsey Number 27 in VFL/AFL history.

The jumper continued its ruck legacy through Steven Alessio, who wore #27 from 1993 to 2003, playing 179 games and kicking 191 goals. Alessio was part of Essendon’s 2000 Premiership side, and ranks 8th all-time for goals kicked in the number across the competition.

Other Premiership contributors in Guernsey Number 27 include Bruce Waite in 1965 and Bob Bradley in 1949.

In the modern era, Zach Merrett played his first 20 games in Number 27, whilst Mason Redman has worn #27 since 2016, establishing himself as a long-term custodian of the jumper and continuing into 2026.