Sheedy has just seven games left as an AFL head coach and will lead his Greater Western Sydney side into battle against the Bombers at Skoda Stadium on Saturday.
The 65-year-old coached Essendon in 634 games between 1981 and 2007, leading the club to four premierships.
He doesn't think the AFL will ever see another tenure like that, with succession planning now the way to go as the Giants have done with senior assistant Leon Cameron, who takes over next year.
But he would like to see clubs give coaches a decent chance, like Geelong did with Mark Thompson, keeping the faith through some difficult times before he ultimately led the Cats to two flags.
"I don't think we'll see it again. I think the coaches will burn out," Sheedy told AFL.com.au.
"They won't do it 27 years. Not in my life, and hopefully I've got a bit to go.
"I think the Swans got it right. They had Roosy (Paul Roos) in there for a while after Rodney Eade and now (John) Longmire.
"And Mark Thompson was a good lesson to everybody.
"If you think you've got a good coach, keep him there until you get that chance and they're up and away."
Sheedy naturally looks back very fondly on his time at Windy Hill, although interestingly the premierships aren't his fondest memories.
"I think the players were the best part of my time there, not the premierships," he said.
"The exciting blokes I coached. From the Maddens and the Danihers through to the Watsons and the Hirds and the indigenous players.
"I probably coached two of the most exciting Aboriginal players ever in Michael Long and Gavin Wanganeen."
Sheedy will need to be at his coaching best this week as he tries to lift his side to face a Bombers outfit hell-bent on maintaining its place in the top four.
The Giants have also faced a week of scrutiny after their 129-point loss to the Sydney Swans last week, but Sheedy is remaining typically upbeat.
"We have to bounce back. It's been a tough week for everyone," he conceded.
"We'll be OK. Our form against the Western Bulldogs two weeks ago was pretty good and so was Essendon's against them last week.
"At the 110-minute mark of both games we were probably about the same, with a kick or two in it.
"And we're always competitive against the Bombers. It'd be an insult to my intelligence if we weren’t.
"I drafted half the team."
GWS did lead Essendon at halftime in round six this year and was also competitive against the Bombers at Skoda Stadium last season.
The GWS-Essendon match will be followed by English Premier League giant Manchester United's clash against an A-League All Stars team across Sydney Olympic Park at ANZ Stadium.
The Giants are hoping to boost their crowd by offering free entry to anyone who has a ticket to the All Stars game.
But Sheedy is devastated former United manager Alex Ferguson won't be making the trip after the GWS coach visited him in Manchester late last year.
"Totally shattered. We could've had a red together," Sheedy said.
"We would've got him a couple of nice Aussie reds, a bottle of Grange or something."
James Dampney is a reporter for AFL Media. Follow him on Twitter @AFL_JD
