Reynolds grew up supporting Carlton and sold lollies outside Princes Park on match days. He had several relatives who also became League footballers, including his brother Tom, cousin Max Oppy, and grandson Joel.
When Reynolds won his first Brownlow Medal in 1934, Fitzroy champion Haydn Bunton, Sr., whom Reynolds had narrowly beaten to win the award, was the first person to telegraph his congratulations, a sporting gesture that Reynolds deeply appreciated.
In June 1947, it was announced that Reynolds would start writing about football for the now-defunct Melbourne newspaper The Argus.
Like many footballers, Reynolds was also a noted cricketer. He was a successful medium-fast bowler for Essendon Cricket Club but gave up the game when it started to interfere with football. In January 1949, he made a return to district cricket when Essendon batsman Ken Meuleman was picked for State duty.
After being re-elected yet again as player-coach by the Essendon committee in February 1949, Reynolds guided the Bombers to the Grand Final against Carlton, which they won by 73 points. Reynolds, who was playing his 299th game, described it afterwards as "the best Essendon performance he could remember."
Off the field, Reynolds was a shy and private man, noted for his humility about his footballing achievements.
Just three days before his death, after being given a standing ovation by the crowd at the "Champions of Essendon" announcement dinner, at which he was named the greatest Essendon player of all time, Reynolds was visibly moved and stated "I don't deserve this honour... Bill Hutchison was the best player I ever saw."
Reynolds' funeral was held at St Paul's Cathedral, Melbourne on 6 September 2002. After the service the hearse made its way to Windy Hill, where Essendon fans had gathered to farewell their greatest player one last time.
His family's link with Essendon continued when his grandson Joel Reynolds was selected by the club in the 2001 AFL Draft. He made his debut in Round 3, 2002 against Brisbane at the Gabba, with Dick watching from the stands.
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