Only three other champion players – Haydn Bunton Snr, Bob Skilton and Ian Stewart – have achieved the feat of three Brownlow Medals.
The following year at age 25, Reynolds became Essendon captain-coach – a position he kept until 1950.
Under his guidance, Essendon won four premierships – 1942, 1946, 1949 and 1950 – and were runners up in 1941, 1943, 1947 and 1948.
Reynolds appeared in 27 finals, kicking a club finals record 51 goals, and after his playing career finished continued coaching the club until 1960.
The champion footballer died in 2002 and the Reynolds family have now decided to auction the Brownlow Medals as one lot with a catalogue estimate $200,000-$250,000.
The auction contains many other football highlights including the 1933 South Melbourne premiership medal belonging to Fred Backway who played for the club in 1933-34 and then went onto play for Melbourne 1935 and 1937 and Fitzroy 1938.
A major attraction is Essendon captain (1998-2005) and 1996 Brownlow Medal winner James Hird’s football jumpers, including the one he wore in his Brownlow year.
One of the jumpers, carrying the number 49, is the one in which he played his first four games. The others carry the number 5 for which he is better known.
On the cricketing front, iconic Australian batsman Don Bradman’s 1934 baggy green Test cap is being offered for auction with a catalogue estimate of $120,000-$150,000.
Bradman originally gave the cap to his golf coach Jack Bahen, one of Australia’s pioneer professional golfers.
On Bahen’s death, the cap passed to his daughter Gretta Richardson who in 1993 loaned it to South Australia’s Mortlock Library. At the time, the library was displaying Bradman cricket memorabilia.
Included with the baggy green is a 1993 letter by Don Bradman regarding the item and a copy of a press clipping in which both the cap and the exhibition are referenced.
The baggy green later became the centrepiece of the South Australian State Library’s Bradman exhibition from 2003 to 2008.
Also included is a DVD with 1950s footage of Bradman and Bahen playing golf at Royal Adelaide.
Champion Australian Test fast bowler Dennis Lillee’s baggy green Test cap also is up for grabs with a catalogue estimate of $18,000-$22,000.
Lillee played 70 Tests between 1971 and 1984 and took a record (at the time) 355 Test wickets.