Reynolds was one of the greatest players to ever play the great game of Australian rules football club and one of the best rovers the game has seen. He went on to play an astonishing 320 games for the Essendon football club, a record surpassed only by Simon Madden, and it was the League record until 1974.
Reynolds is one of four footballers to have won three Brownlow Medals, the others being Haydn Bunton, Sr., Bob Skilton and Ian Stewart. This record alone places him into an echelon above most others that have played the game.
He had no fear about going in to get the ball and his weight enabled him to compete with bigger players and often out mark them. His balance and ball sense made him a real artist and he was renowned for his superb dash away from packs. He could run close to the ground at full speed.
Reynolds was labelled an inspiration and affectionately nicknamed King Richard when he led Essendon to the 1942 premiership, where his best-on-ground display brought an end to an 18-year premiership drought for the club. He won Essendon’s best and fairest award in 1934, 1936, 1937, 1938, 1939, 1942 and 1943 and was runner-up in 1935. His seven best and fairest awards is equal most with Bill Hutchison. He headed Essendon’s goalkickers in 1943 with 31 goals and was second top in 1939 and third top in 1937, 1938, 1941, 1942, 1945, 1947 and 1949.
King Richard’ took over as joint coach with Harry Hunter and at the end of the year he was appointed captain-coach at the age of 25. Under his reign, Essendon went on to win premierships in 1942,1946,1949 and 1950. For five years after he took over, the Dons were never out of the four. This was an incredible turn around for a team that had been down for so long. The Dons were runners-up in 1941,1943,1947 and 1948. As well, they were third twice and only twice out of the four.
His 27 final appearances have been surpassed at the club only by Bill Hutchison. He kicked 51 goals in finals, more than any Essendon player. He also played in six preliminary finals and 10 grand finals, the equal club record.
In 2004, a statue was made in his honor during the 2004 Parade of Champions at the Melbourne Cricket Ground.
1933 – 1951 Essendon
- Essendon premiership captain-coach 1942, 1946, 1949, 1950
- Brownlow Medal 1934, 1937, 1938
- W. S. Crichton Medal 1934, 1936–1939, 1942, 1943
- Essendon captain 1939–1950
- Essendon leading goalkicker 1943
- Australian Football Hall of Fame legend 1996
- AFL Team of the Century (half forward flank)
- Essendon Team of the Century (rover)