“Thought I’d go to jail before I played 150!”, the ever-affable Jimmy Webster quips as he slips off his St Kilda guernsey post-MCG photoshoot and trades it in for his far more comfortable training threads.

You can’t help but crack a smile when you’re around Jimmy. A dry one-liner is always banked up and ready to be thrown out without him skipping a beat; the nonchalance he carries with him part of the charm that has endeared him to Saints fans for over a decade. 

The little grins are certainly on show as his teammates notice the famously elusive defender is making one of his rare media appearances on the eve of a significant weekend for both he and the club. “Just a bit of media!”, he says chipperly as he lopes past them.

Saturday’s milestone is twofold for the wily veteran. First and foremost will be 150 games up after 12 hard-fought campaigns; an achievement only 62 other St Kilda players have reached before him. 

But far more poignant is the fact that after all the adversity and setbacks he’s faced along his rocky road in red, white and black, this weekend’s match will staggeringly mark the 30-year-old’s first finals appearance. 

Sure, it’s just another game for Webster that just so happens to be a milestone rolled into a final. Yet the no-frills defender can’t help but admit it’s a career highlight that’s been a long time coming, and one he thought he may never have reached.

“It’s been nice over the last few years to string a few games together,” Webster told saints.com.au with a trademark smirk.

“Obviously I’ve been in the system for 12 years now which is a long time - I’ve really taken my time to get to 150! - but the last few years have been kind to me with not too many injuries. 

“It is something I have thought about a little bit… to play 150 games and reach it in my first final is something that’s going to be pretty special.

“To eventually get there after everything is something that I’m really proud of.”

Webster carries a few more war wounds with him compared to when he first joined the Saints as a gangly teen from Tassie with toothpick-like arms and a guernsey a few sizes too big. 

A decade on there’s now the scraggly beard, windswept hair flapping about as the MCG swirl picks up, a bit more muscle, the bumps, scars and bruises from years of injury setbacks, and above all, the face of a man who has been through far more than his larrikin-like exterior would suggest.

Webster has always had a way of finding light in dark times. 

Through dwindling team success, extended and repeated stints on the sidelines, family heartbreak and the deprivation of September football, he has continually managed to turn moments of travesty around.

The elation of Webster’s debut in of itself was one born amid immense tragedy, coming less than a fortninght after his family home in Tasmania burned down.

In a way, albeit on a scale incomparable to the Webster family’s loss all those years ago, his journey to 150 games has followed a similar path: hardship has been a constant, but he has found a way to march on.

Even this season, face caved in after a heavy hit which ended in a fractured cheekbone during the club’s 150th Anniversary Game at the ‘G, Webster called out from the interchange bench to the club medicos who were on the phone to his wife: “Tell Richael we’re going back to Tassie!”. He was back in the thick of it again six weeks later, hurtling himself into contests like nothing had happened.

Before that, however, was what nearly seemed like the end of the road. 

A year-and-a-half on the sidelines battling back, hamstring and hand injuries throughout the COVID-affected 2020 season had Webster not only fighting to get his body right, but arguably to keep his career alive. 

That year saw him miss the Saints’ first finals berth in almost a decade, but in true style, he dug in to flip the script.

It was a new role for the leading left-foot distributor when he did eventually crack back into the senior line-up the following season, assuming the lockdown role of Ben Paton, whose double leg break in the pre-season left a hole in the Saints’ squad. It is one Webster has since filled with aplomb.

After taking 10 seasons to reach the coveted 100-game mark, it’s only taken another two-and-a-bit to hit the next 50 games. It’s not quite on Callum Wilkie’s level, but it’s close to it. 

Just how Webster has kept up that upbeat personality and humour despite it all is something he can’t quite put a finger on though. It’s just part of that Jimmy Webster fabric that has him at RSEA Park all these years later, and at long last, in September.

“Footy’s such a funny game sometimes, you ride the highs and ride the lows, and that point in 2020 was pretty low for me. Obviously playing finals is great for the club… but I didn’t think I’d ever taste it,” Webster said.

“I was going through a lot of injuries, had done my hamstring a couple of times and had hurt my back and done a few other things along the way. It wasn’t the best time for me."

Webster isn’t really the type to look back and reflect; everything quickly shifts back to the here and now. The past is the past. 

From a footy sense, it’s as true as a week-to-week proposition that you can get. He’s not a thinker, but a doer. 

Flying into contests with a mixture of brazenness and courage - a facet of his game that has persisted through all 12 seasons - is exactly that. Do what needs to be done for the team is priority one in Webster’s mind; the thought of any potential injury comes later, sometimes to his detriment.

This week though, there has been some time to contemplate on the journey to-date and how much it means to the Webster clan. His mum, dad and siblings will all be making the trip from Tasmania to see him in action, while 10-month-old son Flynn will be able to tell his friends in years to come that the first AFL game he went to was for his dad’s finals debut.

“A lot of people say being a dad changes your life, and I didn’t really think it would change it that much. It has!” Webster said.

“Even the little things like going to get petrol, you can’t jump out of the car and run in and pay for it, you’ve got to bring the little fella in with you. Same with going to get groceries and that. He’s going through teething at the moment which is a bit of a handful, but Richael’s been amazing.

“Having Flynn there on Saturday will be really special… it’ll be something I’ll never forget. His nap-time is between 1-3 normally, so hopefully he’s not too grumpy on the day!

“Fatherhood is hectic at times, but I wouldn’t change it for the world.”

Even though finals football is brand-new territory for Webster, there isn’t much change in how he and the club are approaching it between this week the ones prior, despite the justifiable hype.

‘Relax and be calm’ is the prevailing message from St Kilda’s seasoned September campaigners in coaches Ross Lyon, Corey Enright, Lenny Hayes and Robert Harvey. You couldn’t ask for a bit of advice more relevant to Webster if you tried.

Saturday will come and go, and irrespective of the result, Webster will finally have a finals game to his name after 12 seasons which have more than tested the mettle. And through the rollercoaster that’s been his career, he wouldn’t change a thing. 

Well, maybe a few things.

“I broke my face in two earlier in the year, I’d probably change that!” Webster said with a chuckle.

“In all honesty though, I feel like you build resilience when you do go through injuries and stuff. So maybe I wouldn’t change it.

“Yeah, it would be nice to play a few more finals and all that, but we’ve got a massive opportunity this weekend. I’m looking forward to being a part of it.”