The most recent Brownlow medallist from the Bombers is current coach James Hird who took out the honour in 1996 when he finished equal winner with Brisbane champion Michael Voss.

In 1993 Hird’s premiership teammate Gavin Wanganeen won the award in the Bombers premiership season, becoming the first indigenous player to claim the Brownlow.

Club great Dick Reynolds sits among the games elite as both a triple Brownlow medalist and also the youngest player to ever win the award.

Reynolds was just 18 years old when he won the medal for the first time in 1934 and went on to win it again in 1937 and 1938.

Legendary rover Bill Hutchison won two Brownlow medals during his career. He was originally named runner up in the 1952 medal after losing in a count back to Roy Wright before later being awarded the medal in 1989 when the rules were amended to allow equal winners.

Hutchison went on to win the medal outright in 1953, finishing his career with 172 Brownlow votes, the highest of any Essendon player.

Graham Moss came to the Bombers in 1973, taking out the club's best and fairest award in every season before winning the Brownlow medal in 1976, his final season at the club.

The last strong contender for the medal from Essendon was in 1999 when midfielder Mark Mecuri finished second to Hawthorn’s Shane Crawford. The 99 medal was the last time a player from a team not finishing in the top eight has taken out the award.

Jobe Watson will be aiming to break that 13 year hoodoo and take home Charlie tonight, in the process becoming the sixth Essendon player of all time to claim the honour.