Whether it's scripted theatre or simply fortuitous, Swans ruck Grundy says the apparent coincidence of his milestone match against his former side isn't lost on him.
After his dream of being a one-club player ended when Collingwood pushed him out in 2022, the 32-year-old imagined he'd be at Melbourne for the long run after signing a five-year deal.
That ended after only one season when then-coach Simon Goodwin's experiment to refashion Grundy as a forward in partnership with the all-conquering Gawn failed.
Goodwin, the 2021 premiership coach, has since joined Grundy at the Swans as a coaching director after being sacked by Melbourne in August.
"Fortuitous or meant to be, don't really believe in coincidences, right?" Grundy said on Wednesday.
"It's funny how sometimes the theatre can be scripted like that.
"I can't speak highly enough of the impact Simon's had, and I think coming up here to Sydney, one thing I have tried to do is just hold my head high.
"I've tried to just do the very best I can, and sometimes that's good enough, and sometimes it's not, in the eyes of others.
"In game 250 this week, I'm just trying to focus on what makes me me."
Focusing on what makes Grundy a two-time All-Australian ruck will be crucial for the ladder-leading Swans (6-1) against a revitalised Demons (5-2) side.
Grundy has been an anchor for a Sydney side missing Isaac Heeney on occasion and Errol Gulden long term, while in-form Gawn and first-year coach Steven King have breathed new life into the fourth-placed Demons.
"You can expect, probably, Max to talk a lot of dribble, he usually does," Grundy said.
"He's obviously the all-time great, has been an absolute stalwart, what he's contributed to this game.
"I was so fortunate to play with him for 12 months there at Melbourne, and expecting him and Melbourne to be at their very best this week.
"They seem to be really refreshed and rejuvenated under Steven King, so it should be a good game.
"I just try and be a bit of a firestarter ... I try to see myself more as a midfield, follow-up player."
A reunion with Melbourne is just one of many coincidences in Grundy's "colourful" career.
The often philosophical ruckman recalled a conversation with Swans coach Dean Cox that took place years ago.
"I remember, probably in my third year, going to my manager's Christmas party in Prahran and having a beer with Coxy," Grundy said.
"I was just picking his brain, I was probably 20 years old at the time.
"And I just remember taking so much out of the 20 minutes that he gave me.
"He was at the top of his game, still playing at the time, and now fast-forward many, many years down the track, I've got his knowledge.
"I was so ... grateful, just to fall in love with my craft again."
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