Among the drought-breaking premiership side of 1990 was then 22-year-old Gavin Crosisca, a Queenslander in only his fourth season at the top level.
He kicked two goals in the game-defining second term - the first on the run (and on his left boot) and the second after claiming a contested grab over a pack.
Between 1987 and 2000 Crosisca played 246 games for the club and carved out a reputation as a hard and unrelenting player with an appetite for the contest. He placed in the Copeland three times.
While his on-field achievements were elite, his contributions to the Collingwood Football Club since his retirement have been equally important.
He joined Return to the Nest to chat to host Nick Maxwell about his (at times tumultuous) journey.
The 'weird' footy code
"I grew up on the south side of Brisbane and we were not a sporting family," Crosisca said.
"Dad played a little bit of rugby league but for me to fall into Aussie rules footy as a young kid was quite weird in Queensland.
"The Moorooka Roosters sent flyers around my primary school - I was in year one or two - and I took the note home to mum.
"I started playing as a seven year old and in under 7s you're very easily moulded, I must have been a good listener."
Crosisca played both league and Aussie rules until he was about 15.
"Playing two codes every weekend was too much and thankfully for me I chose AFL," he said.
"The first time I knew I might have been alright was when I captained my under 12s side in a carnival and I was the standout at that level.
"I won best player at this carnival and that gave me a little more confidence and that grew with the interest from down here (in Melbourne)."
Almost a Blue
"The recruiter Collingwood had at the time was Billy O'Keefe, he would watch junior footy all over the place," Crosisca said.
"The draft came in in '88 so it was a little after me, I signed a contract at the end of '84.
"Any club could have picked me and I initially signed with Carlton because I was overwhelmed with the attention and just wanted to get it sorted.
"Unfortunately for Carlton they gave me a two week 'get out' clause if I changed my mind.
"I spoke with Andrew Ireland who was running the QAFL and he said to have a look at the lists and teams and see what team I was going to fit into.
"The pies at that stage were struggling, so I changed my mind.
"Carlton flew mum and I down for the '85 grand final, so we had that free trip and then went with Collingwood... thanks for the holiday."
Crosisca's earliest memory of his time in Melbourne was that year's Christmas party.
"I think it was at Mark Williams' place in Kew, this mansion of a house with a tennis court and a pool and I was just this shy kid from Queensland," he said.
"Everyone was having a drink and enjoying themselves and it made me feel welcome really quickly.
"The other early memory is the goddamn tan track.
"There was always a Saturday morning tan run which always caused a bit of pain.
"If you ask Brian Taylor he will say I was the laziest trainer in history... I feel like I was a solid trainer but I didn't like running.
"That's grown on me since and I love it now."
Flying the flag
Crosisca played under 19s and trained with the senior side in the '86 season.
"There was a handful of us that would always train with the seniors and reserves so that was a great insight," he said.
"We had a pretty solid team but all the talk was about the Kangaroos and Dennis Pagan and his group.
"Keith Burns was an old school coach, he was hard as nails and really set us up to be able to handle the rigours of AFL footy."
After winning the under 19s flag Crosisca was straight into the senior team for Round 1 the following season - he played seven senior games in 1987.
"Later in the year Mark Orval, who was a former roommate, was playing on Jim Stynes and for some reason he couldn't defend someone without fighting them.
"He just started fighting so I thought, 'geez, I have to fly the flag here'.
"I had never hit anyone in my entire life but I got a week for that."
It was his one and only suspension in 246 games.
Kay
Since their move to Melbourne, Kay had become a maternal figure for a number of players living at the Coventry House.
"It was a six or seven bedroom place opposite Vic Park," Crosisca said.
"Mum was there looking after us, cooked and cleaned and all that stuff which made it feel like home for all those guys from the country.
"I'm so thankful for 1987 - she saw me play AFL games and she was well entrenched with the Dolly Grays and enjoying her time here.
"Before our last practice match in '88 she spent two weeks in hospital after suffering a heart attack.
"Tech and treatments back then weren't what they are now."
Two weeks after she was discharged from hospital, Kay passed away.
"Back then, boys and men had this mentality of 'keep it moving'," he said.
"I didn't feel like there was any help and I don't know if I would have accepted any help anyway.
"We all grieve differently and I was a bloke that shut down and bottled it up.
"I'm glad things are different now for my kids - even at the footy club now, you talk about connection and love and say 'I love you' to each other.
"It is important for men to speak about what's going on for us, no matter how embarrassing or shameful we think it might be."
"I used a lot of drugs and drank a lot of alcohol to manage my internal stuff.
"When I got clean and sober in 2011 I certainly reflected on my past and would have probably grieved her more as a 43 year old."
The premiership window
Crosisca said the window the Collingwood team of the late '80s and early '90s was in was reminiscent of the window the Melbourne Demons are in currently.
"Leigh Matthews was as hard as nails and if he said 'run through that wall' you asked, 'how far past it do you want me to go?'
"That's part of the reason I was as hard as I was - I knew that's what he wanted.
"I didn't have a male role model in my life so my coaches were the men I looked up to.
"I would play wherever I was told or back into a pack for the validation from the coaches.
"In 1990 we had a really consistently strong year - we had a belief that no matter who we were playing we would give them a run for their money."
When asked if there was a moment on Grand Final day when the playing group knew they had the flag locked, Crosisca said they were never certain.
"We had to contend with the Collywobbles - that was a real thing," he said.
"The week of the Grand Final we were thinking, 'should we be here?'
"Even during the game we were thinking, 'shit, we're only eight goals up.'
"Collingwood being in a Grand Final for the first time in 32 years, Melbourne was just crazy.
"Leigh really settled us and kept us on track."
Addiction
Over a decade after his retirement from football, Crosisca revealed the drug and alcohol addiction he had battled during his playing career.
"I started smoking dope the year I moved out of home, before I came down (to Melbourne)," he said.
"I know now that there is a genetic component to addiction - it doesn't guarantee that you will become addicted but if you start using mind altering substances it is likely you'll be addicted quicker.
"For me it helped shut all emotions down... it was a solution for me for being very uncomfortable as a kid.
"I looked like I fit in but internally I was really uncomfortable, I felt like a square peg in a round hole and the drugs took that away.
"Mum didn't know about it and the guys at Coventry House didn't know about it.
"I was embarrassed and ashamed but it was good medication for me, it helped me sleep.
"It sounds ridiculous but that's what my mindset was."
Crosisca kept his marijuana use a secret from wife Nicole for a long time.
"I experimented with using amphetamines in the off season in '89 and that set me up for what was going to happen," he said.
"That drug made me feel all the things I lacked.
"When you have low self esteem and low self worth, to use an amphetamine drug gives you confidence.
"I didn't mix alcohol and drugs unless it was a big night and none of the boys knew about it.
"The drug addiction didn't really start until I finished playing.
"Footy was still number one and it meant everything to me.
"When I retired that's when the wheels fell off, it almost happened instantly."
He struggled with losing his sense of identity.
"I was a very controlled user, using little bits at a time over a long period of time... for 10 years," he said.
"I started stealing and all that addiction crap we do so we can fund our habit.
"If you said to me at the time that I needed to stop, there was no way (I could have).
"Without support there's no capability of you being able to stop - when you're in full blown addiction the obsession and compulsion to use is just horrible."
11 years on, the 53-year-old is the director of Sober Living Rehab - a drug and alcohol rehabilitation service.
"I know there's a way out, if someone is suffering from alcoholism or drug addiction, there is a way out," he said.
Transforming the Past Players Association
Crosisca's involvement in the Collingwood Past Players Association has given the organisation a new direction and sense of purpose.
"There has always been a vision (for the Past Players Association) to prepare players for life after footy," he said.
"The average AFL career is still only four and a half years or 29 games.
"How are they coping with the adulation of being a Collingwood player and then being a nobody and going back to school?
"It is disappointing that guys don't know what the AFLPA do, but it excites me because there's so much opportunity for them.
"We are separate from the footy club - we always thought it was the club's responsibility but why should it be when we're no longer playing?
"The club is about wins and losses and if you're not contributing to that, it's fair enough.
"Our Past Players group is doing so much more than other clubs and we want to show the way - we need to do more."
Listen to episode three of Return to the Nest here: