During his long period as one of the AFL's most courageous midfielders, brutal collisions and bloodied bandages seemed as commonplace as tackles and handballs.
As his career gradually ebbed towards its conclusion, Bolton spent more and more time as a dangerous forward, eking every last ounce out of his footballing career.
But his time in the middle of the ground, winning balls in dispute and repeatedly putting his body on the line, is the way the 33-year-old will most fondly be remembered.
It was a trait championed by his grandfather as the way football was supposed to be played.
Yet there has been a changing attitude towards utter fearlessness on the field and the 'badge of honour' that comes from copping hits to the head in the pursuit of a football.
In America's National Football League, a number of studies have been commissioned about the long-term effects of concussions on professional gridiron players.
Just last month, the NFL reached a $US765 million settlement over concussion-related brain injuries, with the money to be used as compensation for those impacted and for further medical research.
As he prepares to play his 325th game in Saturday's preliminary final against Fremantle, Bolton sat down for a chat with AFL.com.au and revealed he had become a keen student of concussion research.
"I'm certainly not as gung-ho as I was when I was a young kid and that's probably with all the research that's coming out of the States," Bolton said.
"I still remember my grandfather saying 'it's better to wake up in an ambulance than pull out of a contest'.
"But after I suffered a couple of concussions, even he changed his attitude.
"Now he says 'you don't want to be a dribbling mess when you're an old man'.
"I've looked into some of what has been happening in the States and depression and different mental illnesses post-football is a shocking thing.
"We need to be really mindful of that."
When Bolton's remarkable career does come to an end, either at Patersons Stadium or at the MCG the following week, he will start getting his head around some events that will initially seem totally foreign.
For example, for the first time since well before he was legally allowed to drink, Bolton won't have his mind on pre-season training.
As his former teammates gear up for the arduous preparation that is required to survive on another AFL season, Bolton has other ideas.
"I'll probably sit at the end of the 3k time trial, maybe with a beer in hand, and just watch the guys slog it out in 30 degree temperatures," he said, flashing that trademark smile.
"I might get away with a few of the guys for a bit of closure - I never used to like missing a footy trip - but from there I just want to get into the post-footy career."
Hopeful of finishing his 15th and final season with a third premiership, Bolton has been preparing for life after football for some time.
The boy who attended St Bernard's College in Essendon and played with the Calder Cannons is now well and truly a Sydneysider, where he will continue to live with wife Lynette and his young daughter.
And he has big plans for his future.
"I'm accredited as a player agent so I'll do some work with my manager Ben Williams from Players Ink," he said.
"I'm looking forward to that, as well as a bit of media and also some corporate work with the Swans.
"I really just want to stay involved in footy. I love it and I love that analysis of it, plus also that mentorship of younger guys."
Bolton is the stereotypical 'footy head' and admits he'd "love to play forever".
In recent years he has proven a more than handy forward, breaking his personal record goal tally in each of the last three seasons, including an excellent 28.17 in 2013.
If he had chosen to play on, the club may well have agreed, but it is a sign of his selflessness Bolton believes it is time to give another young Swan his chance.
"That was part of the reason behind my decision," he said. "I'm really confident in the list we've recruited and blooded.
"It augurs well for the future and we've still got plenty of experience there as well who have played in big games."
Credited with the most career tackles (1483), plus the most tackles ever in one game (19), Bolton has a place in the record books.
He will also finish just shy of teammate Adam Goodes in the Swans' all-time games played list.
Twitter: @AFL_JD
