[5] Buckley spent the majority of his football-developing years (aged around 10–17) in the Northern Territory, and thus he has occasionally been regarded as a Territorian.
He rebelled at the age of 14, opting to play tennis rather than football, but then his father Ray sent him to boarding school at Victoria's Salesian College in Sunbury to rekindle his enthusiasm in a footy environment.
[8] While at St John's, he played school football alongside a number of other future AFL players including Scott Chisholm, Ronnie Burns, Andrew McLeod and Michael Long.
[citation needed] He also played cricket for the "PINTS" social club, alongside Michael Tunn from Triple J.
Buckley challenged the AFL draft system and sparked controversy by initially resisting a move to Brisbane.
His dreams were to play in Melbourne due to its culture in the sport, therefore felt the Bears were an undesirable career option.
At the end of the contract he attracted strong interest from all Melbourne-based clubs, chiefly Collingwood, Geelong and North Melbourne.
[10][5] Buckley was adamant that the move was the right career direction, with the belief he had more chance of winning a premiership with Collingwood[citation needed].
Buckley competed in the last game at Collingwood's long-time home ground Victoria Park against one of their main rivals, the Brisbane Lions.
The fact that Collingwood was so close in the end had to do with his dominance against the vaunted Brisbane midfield, including captain Michael Voss.
In 2003, Buckley received his highest individual honour, the Brownlow Medal in a three-way tie with fellow South Australian-born players Mark Ricciuto (Adelaide) and Adam Goodes (Sydney).
He started the season in usual domineering fashion in the opening three rounds, but missed seven of the next eight matches with hamstring problems.
At the end of the 2006 season Buckley indicated the possibility of him standing down as captain of the club, saying that James Clement might be a likely choice for the position.
However, they recovered to win their next ten matches and finish the home-and-away season in fourth place with a record of 16–6.
However, they lost comfortably to eventual premier Sydney in the Preliminary Final at ANZ Stadium to bring an end to the 2012 season.
They couldn't quite find the consistency of previous seasons and finished the year in sixth place with a 14–8 record.
They played Port Adelaide in their Elimination Final at the MCG and slumped to a shock 24-point loss, which caused Buckley to call into question the club's culture.
Buckley's personal connection with young GWS star Adam Treloar helped secure the player for Collingwood in the 2015 trade period.
[24] The Magpies' 2016 season commenced with a heavy 80-point loss at the hands of Sydney and what would be a career-ending injury for Dane Swan.
[28] This form continued into 2019, Collingwood finished fourth on the ladder with a 15-7 record and defeated top-of-the-ladder Geelong in the first week of the finals.
The club was fined after Buckley and assistant coach Brenton Sanderson breached COVID protocols during their stay in Western Australia.
Buckley supported Collingwood following a tumultuous 2020 trade period which saw three senior players, including Treloar, depart for a modest compensation.
[32] On 9 June 2021, Buckley announced that he would step down as senior coach, effective after the Round 13, 2021 Queen's Birthday match against Melbourne.
Beginning in 2022, Buckley will present the live program Best on Ground on Fox Footy as well as commentating matches for the network.
[citation needed] On 4 December 2020, Buckley and wife Tania jointly announced they have separated after 18 years of marriage.
[45][46] Buckley has also moved into harness racing and is the owner of the Group One winner Hurricane Jett, a pacer named after his oldest son and trained by highly successful trainer and Collingwood supporter Jayne Davies.