His father is a renowned leader in Australian Rules football and racing.
Now, Dillon has taken what AFL chairman Richard Goyder describes with hubris as "the biggest job in Australian sport".
The 52-year-old will be the AFL's next chief executive officer.
Dillon fell in love with football as a five-year-old - and the sport has loved him back ever since.
"Football has been a defining part of my life," he told reporters on Monday.
"I have been so fortunate to be involved in footy at so many levels throughout my life, from my first game as a five-year-old at an under-10s match ... right through to junior club and school football.
"I umpired, albeit not very well, during high-school years.
"And then I played community football for 16 years at a senior level.
"I have run an Auskick centre. I have been an assistant coach at senior level for the Old Xavs (Old Xaverians Football Club in the VAFA).
"And I have coached junior girls footy at Kew Comets for five years.
"And I can tell you, in my 23 years at the AFL there has been no tougher job than trying to run a training session on a Friday afternoon for an under-13 girls team."
Dillon's grandfather, Victoria's first ombudsman John Dillon, was knighted in 1980 for distinguished public service.
His lawyer father, also named John, is a former VAFA president and chairman of the Melbourne Racing Club who played for De La Salle.
"My love of football was formed playing matches on Saturday morning and then spending the afternoon watching De La Salle play - and then spending Saturday nights playing scratch matches on the same oval for hours on end," the AFL's new CEO said.
"While Dad introduced me to community football, it was Mum who took me to my first VFL game - it was between Richmond and Melbourne at the MCG on a cold day in May of 1976.
"I loved that game. And even though Richmond were leading at halftime, I made Mum leave so we could catch the train to the De La Salle ground because I didn't want to be late for the scratch match after the game."
After his formative years, Dillon forged a successful playing career: his 290 games with Old Xavs from 1989 to 2005 featured six A grade premierships and he also twice represented the VAFA.
He's a life member of the club, having served on the committee and also as an assistant coach.
"I have seen and experienced first-hand the power that community footy has to connect people," Dillon said.
"And also how important community clubs are, for the football industry but (also) for the wider community as a place where people can come together and be a part of something that is bigger than themselves."
Off-field, Dillon completed a Bachelor of Commerce, and a Bachelor of Laws, at the University of Melbourne and worked as a solicitor at Corrs Chambers Westgarth from 1994.
In 1997, he joined Village Roadshow Limited as legal counsel - a three-year stint ended in late-2000 when he took up the same role at the AFL.
From there, Dillon rose through the ranks, holding positions including general manager, legal and business affairs; general manager of national and international development; general counsel; general manager, legal, integrity and compliance.
In July 2021, Dillon was appointed executive general manager of football operations in addition to his other roles, which he will soon relinquish to become Gillon McLachlan's successor as chief executive.
"It's really important, and I can't stress it enough, that we are a game for everyone," he said.
"I believe strongly in the power of footy to connect people regardless of their background, gender or beliefs.
"And I want to have footy in every home across the country."
13°C