It was 1998. Clarkson was at Melbourne, Longmire at North Melbourne, and they wanted to revolutionise the way the players were represented in all dealings with the game's powerbrokers.
They lobbied their best footballing friends, gained the backing of the biggest-name players and went on a mission to transform the ideology of the AFL Players Association.
Meetings were called, including a fiesty gathering of 80 players where Clarkson expressed very strong views on the need for change. A sub-committee was chosen to interview candidates to become the new chief executive officer of the AFLPA.
When that process was completed, where it is believed Brendan Schwab was highly recommended for the post, Clarkson and Longmire took matters into their own hands and ordered a former teammate to meet them.
That ex-teammate was Andrew Demetriou, who was quickly convinced by Clarkson and Longmire to take over the running of the PA.
Clarkson had played just one season with Demetriou, and Longmire arrived at Arden St just as the now-League chief was heading to Hawthorn. But the ambitious young pair knew they had their man as soon as they met to discuss their plans for the role.
A person involved in the 1998 AFLPA CEO search said this week: "Demetriou was not even in the mix. His name hadn't come up in one conversation to that point. Clarko and Horse (Longmire) just went and met him and he got the job. It was a boat race."
Within weeks of his appointment, Demetriou began the successful fight for massive player wage increases and two years later was running football operations at the AFL. In 2003, he was appointed AFL CEO.
Liam Pickering, another teammate of Clarkson and Longmire - who this Saturday clash as Hawthorn and Sydney Swans coaches in the 2012 Grand Final - remains best mates with both men.
"Yeah, they were heavily involved in the appointment of Demetriou, no doubt," Pickering said. "Given what has happened since, you could argue it was one of footy's great coups."
The country roots of Clarkson and Longmire drew them instantly close on their meeting at Arden St late in 1987. Longmire's first match as a North player was as a 16-year-old in the infamous London exhibition match against Carlton in 1987, when Clarkson broke Ian Aitken's jaw and spent the second half being targeted by his opponents.
The two remained close even after Clarkson was traded to Melbourne at the end of 1995.
Then, when Clarkson secured the Hawthorn coaching job after Peter Schwab's sacking in late 2004, Longmire was also in the mix. Longmire was definitely being considered by the Hawks before he chose to remove himself from calculations, saying he didn't feel ready. And Paul Roos certainly did not want to lose him as an assistant coach at the Swans.
Mark Brayshaw, a current North board member who played with Clarkson and Longmire at the Kangaroos and remains great mates with them, said the two were "beneficiaries of the amazing North Melbourne culture and products of that egalitarian club."
"Judy Francis (an iconic identity at North) loved them both," Brayshaw said. "She loved everyone, but she loved those two a lot, and they loved her."
Of Clarkson, Brayshaw said: "He certainly can be a feisty little customer, that has always been part of his DNA. But it is a misnomer to say that is how he is away from footy. You won't meet a more generous man."
Of Longmire, Brayshaw said: "He's the big monster, a big bloke with a booming voice and a real presence about him."
Brayshaw reflected the views of everyone who knows both Clarkson and Longmire well when he said: "Half of me wants the Swans to win and half of me wants the Hawks to win."
You can follow AFL Media's Damian Barrett on Twitter: @barrettdamian
The views in this article are those of the author and not necessarily those of the AFL or its clubs.