Despite a barren 1930s period for Essendon, which saw the club never finish above sixth position, the arrival of local product Dick Reynolds in 1933 gave supporters something to cheer about each Saturday.

With his perfectly groomed, slick black hair and his chiselled frame, Reynolds was movie-like in appearance and quickly became an idol at Windy Hill. They would yell “Dickie” from the grandstand whenever he swooped on the ball.

In his second season, aged just 19, Reynolds won the first of his record seven Essendon best and fairest awards and, with 18 votes, became the first - and still only - teenager to win the game’s highest individual honour: the Brownlow Medal. According to younger sister, Pixie McNamee - the mother of Australian tennis champion Paul McNamee - her brother was as dynamic as Chris Judd, but a better mark overhead.

Indeed, Reynolds could do it all. Playing all over the field, he was one of the game’s first true ruck-rovers, utilising his speed and endurance to outrun opponents in the middle, before drifting forward to often kick a crucial goal.

In 1937, Reynolds elevated his game to another level, receiving a then-record 27 Brownlow votes to claim his second medal. When he won it again in 1938 (18 votes), he joined Fitzroy champion Haydn Bunton as a triple winner. Only South Melbourne’s Bob Skilton and St Kilda and Richmond champion Ian Stewart have since equalled their remarkable feat.

Dick Reynolds during an Essendon game in 1998. (Photo: AFL Photos)

In 1939, aged just 23, Reynolds was named captain of Essendon and, mid-season, became captain-coach of the club following the resignation of coach Jack Baggott. It would prove an inspiring choice.

The legend of King Richard had only just begun.

This moment is the fifth of a virtual series presenting the Bombers' best 30 moments over 150 years, which fans can vote on for their chance to win prizes. Check out each moment via our virtual experience or vote below.

SCHEDULE OF MOMENTS

Round 1 (May 6-9) - 1872-1939

Round 2 (May 10-14) - 1940-1959

Round 3 (May 15-19) - 1960-1979

Round 4 (May 20-24) - 1980-1989

Round 5 (May 25-29) - 1990-1999

Round 6 (May 30 - June 3) - 2000-2021

Round 7 (June 4-9) - Finals round

PRIZES

Round 1 – One 2022 merchandise pack, including an Essendon New Era Black on Black 9FORTY Snapback cap ($40) and an Essendon Heritage Bar Scarf ($30)

Round 2 – One Essendon Fibre of Football Scarf ($80)

Round 3 - One Essendon Football Club 150-year anniversary commemorative mosaic ($295)

Round 4 – One Essendon Football Club 150-year anniversary commemorative mosaic ($295)

Round 5 – One 2022 team-signed guernsey ($500)

Round 6 – One copy of the Red & Black Collection special 150th anniversary book ($329)

Round 7 – One copy of the Red & Black Collection special 150th anniversary book ($329) and one 2022 team-signed guernsey ($500)