Reynolds is one of four footballers to have won three Brownlow Medals, with the others being Haydn Bunton Sr., Bob Skilton and Ian Stewart.

He was a successful medium-fast bowler for Essendon Cricket Club but gave up the game when it started to interfere with football.

[7] In January 1949, he made a return to district cricket when Essendon batsman Ken Meuleman was picked for State duty.

[7] After being re-elected yet again as player-coach by the Essendon committee in February 1949,[8] Reynolds guided the Bombers to the Grand Final against Carlton, which they won by 73 points.

After the service, the hearse made its way to Windy Hill, where Essendon fans had gathered to farewell their greatest player one last time.