One of the AFL's true warhorses, Bolton would have been right at home in any era.
Currently on 321 games, he is second only in South Melbourne/Sydney Swans history to Adam Goodes' 331.
When he lines up against Hawthorn this Friday night, he will move past Ted Whitten, Stewart Loewe and Tyson Edwards and join Simon Black in 30th place on the game's all-time list.
Making his debut in round 12, 1999, Bolton made 25 appearances over his first two years at the club.
Since then, he has failed to reach at least 20 games in a season just once, back in 2002.
That year he played 19 games.
Between 2005 and 2011, he made 145 consecutive appearances, an extraordinary feat for a player often known as much for concussions and bandages around his head as he was for kicks and tackles.
"I've avoided some of the long-term injuries guys have gone through," Bolton told a packed press conference at the SCG on Monday.
"My heart goes out to people like Rhyce Shaw (who tore his ACL on the weekend) … and that's certainly the dark side of footy.
"I think three games was my longest stint out of footy and that was last year when I hurt my knee.
"It's been an unbelievable journey."
Bolton was also an integral part of a golden generation at a club that spent more than 70 years battling not just for a fourth premiership to add to those won in 1909, 1918 and 1933, but at times to stay afloat altogether.
What he leaves behind is a club now boasting more than 36,000 members, two flags in the past eight years, a comfortable place in the Sydney landscape and a list set to contend for the foreseeable future.
He leaves the club in a very different position than when he joined it in 1998.
"Back then we'd just lost Shannon Grant and Anthony Rocca, who wanted to head back home," he said.
"And the 'go-home' factor was a big part of what was happening back then.
"Now we've got a club that is envied in terms of having a great culture, a great club to be part of, a great supporter base and corporate support."
Many thought 2012 would be his final season, but he wasn't quite done yet.
He has so far eked out 20 games this year and played a key role for a Swans side once again in the top four and challenging for a premiership.
He was never able to secure All Australian honours or a best and fairest award, the type of accolades that wouldn't look out of place alongside his name and list of achievements.
But perhaps it is fitting for a man with a classic blue-collar attitude driven by team success that it is premierships, and not individual gongs, that underline his career.
Bolton picked up his best possession total in driving rain at the SCG against the Western Bulldogs in 2012, his 41 touches putting the Swans on track for a blowout win.
One of the game's most courageous onballers in his prime, he moved into the forward line in the twilight of his career and set personal best goal tallies over the past three years respectively – 19, 23 and then 26 so far this season.
He is credited with more tackles in one game (19) and more career tackles (1467) than any other player since the statistic started being recorded.
"It's just been a magnificent career that this bloke has had," Swans coach John Longmire said.
"He's probably been the best clubman I've ever been involved with.
"Always had a smile on his face, really enjoys his teammates, continues to play good football to this day and is teaching the kids coming through this football club every week and takes a kick out of their improvement."
