The small town in Western Victoria was part of the Bombers' VFL zone and as a young star of the area Clarkson was in the club's sights.
In those days clubs could sign young players on a junior development list before they were old enough to sign with the senior side.
Essendon was keen to sign Clarkson, but he was at school in Ballarat – St Kilda's zone – and would have been unable to return home to play regularly.
As a result, the Bombers freed up his place on the junior list with the promise of a future position at the club.
Clarkson was fine with that scenario, happy that in a few years he would play for the same club at which close family friends Roger Merrett and Glenn Hawker had become famous.
Then came the moment that changed the course of his footballing life.
He signed a form while at school that he thought was necessary to take part in a football carnival.
Clarkson, 16, was unaware that in fact he had signed a form required to opt out of one club's zone and into that of another, St Kilda's.
"Greg Miller, who was a recruiter at North [Melbourne], was very crafty and he would identify talent right around the country," Clarkson said.
"He'd go, 'Craig Sholl's not on Essendon's list, Clarkson's not on that list either – I'll ring him up and see if he wants to come to North'."
Clarkson told Miller he wasn't interested in playing for the Kangaroos because he had verbally agreed to join the Bombers.
Miller accepted this but called back a week later with the startling news that he wasn't set to become a Bomber, but a Saint.
"He said 'You've signed something', even though, as a 16-year-old kid, you've got to have your old man's signature on it as well," Clarkson said.
"I rang Dad and asked whether he'd signed anything – 'Nah'.
"So the papers were botched, but Essendon looked at it and cracked a wobbly thinking I'd done the dirty on them and Greg Miller, who had tracked this all the way through and helped us out, then said,'Well, do you want to come down to North Melbourne?'"
Clarkson would go onto play 93 games for the Kangaroos from 1987-1995 before joining Melbourne for two seasons, where he managed another 43 matches.
He has since won three premierships as Hawthorn coach and will be vying for a third straight flag in 2015.