He then coached Essendon in the VFL/AFL for nearly three decades from 1981 until 2007, winning four premierships and earning acclaim for his unusual and creative approaches to promoting the club and the game.

[4] He played junior football with the local Try Boys society team while attending De La Salle College, Malvern, where future teammate Kevin Bartlett also spent a brief time.

[citation needed] Between 1969 and 1971, Sheedy undertook two years National Service with the Australian Army's 21 Construction Squadron, rising to the rank of corporal before discharge.

Sheedy jumped at the chance to join the up-and-coming Tigers, but a problem emerged when he shifted to Punt Road: the VFA refused to endorse his clearance due to a wider disagreement with the VFL relating to transfer fees.

Occasionally, his teammates blanched at some of his more theatrical attempts to win free kicks or fifteen-metre penalties, and he had the ability to whip opposing supporters into a frenzy.

Since his injury, Sheedy had lived on the edge knowing that if he failed at Richmond it would be the end of the line because of the impending five-year suspension; however, he seemed to have an innate ability to read how far he could push the envelope, and indeed he was never reported during his career, a fact that would surprise most who saw him play.

In an earlier final, Sheedy had ruffled Carlton's captain-coach, John Nicholls, suggesting that he was finished as a player and that Richmond had the wood on the Blues.

Nicholls and his men, stung by media criticism and the attitude of the Richmond players, played a whirlwind first half in the Grand Final, booting eighteen goals to lead by 45 points.

[10] Sheedy made good copy; during the season, Richmond had appointed him as full-time promotions officer, effectively making him the first professional footballer in the VFL.

However, he was shocked when his mentor and idol Tom Hafey left the club due to a lack of support at committee level.

Essendon won four premierships during Sheedy's tenure as senior coach in 1984, 1985, 1993 and 2000 as well as finishing runner-up three more times in 1983, 1990 and 2001 and losing a further two Preliminary Finals by only 1 point in 1996 and 1999.

Sheedy made several moves in the last quarter of the 1984 grand final, when Essendon looked out of the game, and the side scored a come-from-behind victory.

On the recruiting front, prior to the 2000 season, Sheedy lured ruckman John Barnes back to Essendon (a side that had traded him many years earlier) in the 1999 AFL draft after he was let go by Geelong.

However, the milestone was not one to be remembered fondly, as Essendon went down by 60 points to Port Adelaide (a fate that also befell Jock McHale, who lost his 600th game as coach of Collingwood).

[24] Also during the 2006 season, Sheedy took a leave of absence for one game when he injured his shoulder in a collision with defender Dean Solomon at training.

Sheedy's last home game as Essendon Football Club senior coach was against his old playing side Richmond in Round 21, 2007 at the Melbourne Cricket Ground.

[14][15][16] On 9 November 2009, Sheedy signed a three-year deal to be named as the inaugural senior coach of the Greater Western Sydney Giants, which joined the AFL in 2012.

[52] In 2015, Sheedy left and departed from his position as board member of the GWS Giants, to return to the Essendon Football Club in the role of General Manager, Commercial Development and Innovation.

[55][56][57][58] Sheedy's legacy is credited by "some commentators who observed that his considerable achievements were due not so much to abundant natural talent but to determination and the thoughtful application of his abilities".

[10] Despite Sheedy's impressive record in Australian Rules football as a player and coach, "his most profound influence may be the innovations he proposed and supported.

He also promoted the creation of an annual Essendon–Richmond Dreamtime at the 'G match to recognise each club's achievements in supporting the integration of indigenous culture and players.

According to the Sport Australia Hall of Fame, in which Sheedy was inducted in 2009, "For all the Premiership trophies he has held aloft as player and coach, it is this legacy that may give him greatest satisfaction.

"[10] Aside from his venerable coaching and playing record, Sheedy is also noted for his quirky antics, outspoken nature, and wry sense of humour.

The tactic worked, and the Eagles won the toss and kicked into the breeze for the first quarter, although the Bombers inevitably lost by 7 points nonetheless.

In his excitement at winning a close match, with ruckman and forward Paul Salmon kicking a goal 30 seconds before the final siren against the West Coast Eagles, he waved his jacket in the air as he came rushing from the coaches' box.

[64] Another example of his ability to build up and promote matches was in 1998 when he labelled North Melbourne executives Greg Miller and Mark Dawson "marshmallows", referring to how soft they were.

This caused a tension between the two camps, and it came back to bite Sheedy when North Melbourne defeated Essendon in a finals match that season.

In yet another game against the Eagles, Sheedy was fined $7,500 by the tribunal after making a cut-throat gesture to then-Eagle Mitchell White during the half-time break of the Essendon–West Coast clash in Round 15, 2000, also apparently mouthing the words "You... are...

He has also encouraged foreign players to train with his side such as a former American footballer, a skillfully athletic Ethiopian immigrant, and more recently two Japanese try-outs.

Sheedy visited the United States and Canada in 2007 on a tour of North America as AFL ambassador, attending the USAFL National Championships, and was well received from stateside fans.