Under his 10-year watch that began late in 1986, the AFL introduced the draft, salary cap and ground rationalisation – all key planks in making the competition more even.
The Australian Football Hall of Fame, a crackdown on racial and religious vilification and the first serious drug code were also features of his time in charge, yet he counts none of the above as his biggest accomplishment.
Instead, Oakley points to the appointment of Richard Colless as chairman of the Sydney Swans in 1993 as the development that gave him the most satisfaction.
In an interview with the AFL Record ahead of the release of his memoirs from his time with the League, The Phoenix Rises, Oakley said the Swans were a complete mess at the time.
The AFL's head football honcho Alan Schwab has been seconded to Sydney to run the Swans, who were bottom of the ladder, mired in debt and had 3000 members at the time. And then Schwab died suddenly, leaving Oakley fearful of finding anybody else to pick up the pieces.
"The Swans had struggled all the way through and when Alan Schwab died, I thought that was our last-ditch effort gone. He was the one to get them up and going again," Oakley said. "I was left wondering what I could do next."
Colless was among the initial investors in the West Coast Eagles when they joined the League in 1987 and was that club's inaugural chairman. But he moved to Sydney and was off the AFL scene for the few years.
"He had an interesting time at West Coast but I thought at least he knows what footy is about, he’s passionate about it, he'd be a good cultural fit and not caught up with the old boy way of doing things," he said.
"And the club became financially more stable, more like a real footy club in culture and one that players, sponsors and members all wanted to be part of."
Within three years the Swans had made the Grand Final and in 2005 they broke through to win their first premiership since moving to Sydney and the first for the club since 1933.
Oakley said friends and associates had been urging him for years to put his thoughts and memories from his time at the AFL into print. He added that many current AFL and football industry people had no real understanding of the major challenges the game had to overcome as recently as 30 years ago.
Read the full Ross Oakley interview in this week's AFL Record, available at all grounds. The Phoenix Rises (Slattery Media Group) is available from July 1.
Twitter: @afl_hashbrowne
