Born in Drouin to Alfred and Colleen Ablett, Gary Ablett grew up in the Latrobe Valley in Victoria's Gippsland region alongside his four elder brothers and three sisters. Ablett displayed a love for sport at an early age, winning the state school high jump at 10 years of age. He was also awarded both club and competition best and fairest awards for Drouin at the under-11s, under-12s and under-14s levels. After citing waning interest in school, Ablett dropped out of high school at the age of 15 years to become a bricklayer's labourer.

The 1989 season was marked by the arrival of Ablett's third coach, former North Melbourne Brownlow Medallist Malcolm Blight. Ablett helped the Cats reach the finals on the back of a ten match winning streak to end the regular season. In a 134-point victory against Richmond, Ablett scored 14 goals, breaking a 22-year club record, and moving club legend and former club premiership coach Bobby Davis to laud Ablett as the equal of the legendary Graham 'Polly' Farmer, the finest footballers he had seen at Geelong. His season lowlight occurred in Round 12 when he was suspended for 3 matches after he controversially felled the Melbourne captain, Gary Lyon behind the play.  In his first ever final, the Qualifying Final at the MCG versus Essendon, Gary Ablett kicked three goals, but this was not enough. The Bombers humbled Geelong by 76 points to force the Cats into a sudden-death Semi Final showdown with Melbourne. The Cats posted a 63-point win against the Demons. Ablett kicked seven goals, and helped set up another meeting with Essendon in the Preliminary Final. Ablett kicked 8 goals this time, as the Cats crushed Essendon by 94 points to advance to their first Grand Final since 1967.  Against the reigning premiers Hawthorn in the 1989 VFL Grand Final, Ablett asserted himself from the opening bounce, leading out from full forward, marking the first centre clearance kick and slotting through the game's first goal. By half-time, Ablett had kicked four goals, but the Cats trailed at the main break by 37 points. Ablett kicked a further five goals in the second half, which saw an injury-depleted Hawthorn's lead reduced to just 6 points with less than a minute to go. However, the Cats fell short, and Hawthorn held on to defeat Geelong in one of the toughest Grand Finals of the modern era, winning by 6 points. Ablett's performance in kicking 9 goals earned him the Norm Smith Medal, and in doing so became only the second member of the losing team in VFL/AFL history to be awarded the honour - a performance regarded by many as unrivalled on football's biggest stage. Ablett's 9 goals also saw him equal Gordon Coventry's goals record set in the 1928 Grand Final.

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