The 33-year-old midfielder-turned forward has played 321 games for the Swans, second only on their all-time list to teammate Adam Goodes (331), with both making their senior debut in 1999.
Bolton has played in three grand finals, tasting victory in 2005 and 2012 and defeat in 2006.
Selected with the 8th pick of the 1999 national draft, following a deal which took Jason Mooney to Geelong, Bolton has enjoyed an admirable reputation for his approach to the game.
He has made the most tackles in the game since that statistic was first recorded.
Bolton has always been renowned for his fearless in and under approach and putting his body on the line.
Despite his seeming lack of regard for his own health, Bolton has proven remarkably durable and is set to play more than 20 games for the 12th time in the past 13 seasons.
In the past two seasons he has successfully been converted into a goakicking small forward, bagging a personal best haul of 23 last year and improving it to 26 in the current campaign.
However, growing concerns about the state of his knees along with his desire not to block the passage of one of Sydney's many good young players persuaded him to call time on his illustrious career.
"I'm acutely aware of my body 12 months down the track I don't know how it would be if I had a setback along the way, I might have a mid-season retirement," Bolton said.
"The other thing is I'm aware of our list. We've got some great talent coming through hopefully they can continue to push in.
"That's what I want to see, that's the footy life cycle and it's just the turnover of the list."
He rated full forward Tony Lockett as the best player he had played with.
As a St Kilda fan growing up, Bolton particularly relished his battles with Saints' champion Robert Harvey.
Sydney coach John Longmire said Bolton was a fantastic performer and warrior for the club.
THE JUDE BOLTON STORY:
*Junior Club: Aberfeldie
*Recruited from: Calder U18
*Drafted: 1998 National Draft 1st round selection (Sydney) No.8 traded by Geelong for Jason Mooney
*Senior debut: 1999, round 12 v Carlton
*Senior games: 321
*Senior goals: 193
*Grand final appearances: 2005, 2006, 2012
*Premiership wins: 2005, 2012
*Most disposals in a game: 41 v Western Bulldogs, rd 10 2012
*Most goals in a game: 4 v North Melbourne, rd 3 2013
*Most marks in a game: 9 v Western Bulldogs, rd 10 2012
*Most tackles in a game: 19 v West Coast Eagles, rd 3 2011
*Brownlow Medal career votes: 69
*International Rules series: 2004
*Swans' Most Improved: 2003
*Best clubman: 2005, 2006