THE LAST time – and only time – St Kilda won a premiership was the year Australia replaced pounds, shillings and pence with dollars and cents. Ian Stewart was paid about $10 a game in that season when he held off Carlton legend John Nicholls to win the second of his three Brownlow Medals.

On Sunday night, the Saints will start the 2026 season at the same venue – and against the same opposition – where the club experienced the greatest day in its 153-year history. And in the hours before St Kilda hosts Collingwood at the MCG in Opening Round, the club will celebrate the 60-year anniversary of the 1966 premiership team in the Olympic Room.

Stewart will be in attendance at the MCG, along with most of the living players from that team, including 1967 Brownlow Medallist Ross Smith. All premiership players and their families have been invited. Eight of the 20 players have passed away, but St Kilda hopes that representatives of every player will attend the reunion. 

"A premiership does leave a big statement and you do feel a camaraderie forever. You really do feel that," Stewart told AFL.com.au this week.

"When one passes away – and quite a number that have – it's very, very important when you lose one of your teammates from that premiership era because we have that bond."

Barry Breen has been immortalised for kicking the most important point in St Kilda's history. The commentary by Mike Williamson, 'It's a … point! It's a point, St Kilda in front! St Kilda in front!' has been heard by generations of nostalgic Saints supporters. 

"I've only ever seen the replay twice," Stewart said. "Once was the next day after the Grand Final when we were at a function. I didn't realise that Barry played so well. What a special moment."

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St Kilda has celebrated its only premiership team many times, most notably in 2016 when they gathered at Royal South Yarra Tennis Club to mark 50 years. Then only a few years ago to celebrate the club's 150th anniversary in 2023. Breen says the connection for life isn't just a throwaway line.

"There is a bond that obviously can't be broken, because A, it was the first, and B, it's been the only one, which is crazy, but it is," Breen said.

"There's that bond there, and it doesn't matter if you don't see somebody for 10 years, you go back into that era or that time when you when we were mates and teammates, it's pretty special."

1966 Premiership players Kevin 'Cowboy' Neale (left) and Barry Breen bring out the 1966 Premiership cup to celebrate 50 years since the Saints' premiership ahead of the match between St Kilda and Collingwood at the MCG in 2016. Picture: AFL Photos

Breen was just 18 when he kicked that famous point in his 25th game. He would go on to play a then-club record 300 games – only four men have gone past him: Robert Harvey, Nick Riewoldt, Nathan Burke and Stewart Loewe – in the red, white and black. The moment, 60 years on, is still defining.  

"It's been a defining point in my life, really," Breen said. "Did it set me up for the rest of my life? I think it did a little bit. It gave me cachet and all that sort of stuff in wherever I went in business. Wherever you go, it's there. I'm grateful for it.

"Wherever I go, I don't care where I am in the world, someone will know what I did and want to have a conversation. I've just come off a cruise to the South Pacific, and there are guys on that one came from Gisborne and wanted a photo – and this is in the middle of the Pacific – much to the chagrin of my mates – and they give me heaps about it – so it never goes away; being a premiership player never goes away."

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The Final Story: 1966 Saints triumph

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It has been a long wait for St Kilda's second flag, but Breen believes the Saints are close to contending again after splashing the cash on Tom De Koning, Sam Flanders, Jack Silvagni and Liam Ryan last October, after securing the most important signature of all – Nasiah Wanganeen-Milera – for two more years in August.

"They are pretty tough to win, but I like the way the club's going about it at the minute in terms of their recruiting and whether all that risk comes off or it's going to be found out at some point, but they're having a go," Breen said.

"I like what Ross does as a coach, and he's got plenty of people around him now where he's not the sole man in charge. He's always been a control freak, but he's got a lot of good people around him, which helps the team. 

"They've got some very promising young players that have been promising now for two or three years, so with the experience that they've added around the group, the expectations are high, and I'm hoping that maybe this year they could do it. But it might be next year or the year after, in terms of the age of the players they got, but they've got a good base, and hopefully they can capitalise."

St Kilda has reached five Grand Finals since 1966, including the replay in 2010. Leigh Montagna played in the famous draw, where the Saints came within a kind bounce towards Stephen Milne from reaching the promised land during Ross Lyon's first stint in charge. 

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Recounting the game's last GF draw

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Montagna played 287 games for the Saints and featured in the 2010 and 2011 Grand Finals. The Collingwood games are never far from his mind, but the two-time All-Australian, who is now a leading analyst on Fox Footy and Triple M, doesn't dwell on what ifs. 

"How often do I think about 2010? Every time people like you ask and bring it up; every time people talk about the St Kilda-Collingwood rivalry; every time someone talks about Grand Finals. Yes, you do think about it a fair bit. But I look back on it not with sadness, but with fondness for that whole experience," Montagna said.

"To play in the last ever drawn Grand Final; to get to that moment is so memorable; obviously would have loved to have won the following week, but it does come up a lot. You try and do your best not to think too much of what could have been."

Leigh Montagna looks dejected after St Kilda's loss to Collingwood in the 2010 Toyota AFL Grand Final replay at the MCG. Picture: AFL Photos

St Kilda went hard early and landed De Koning on a mega eight-year deal last year. They beat three other Victorian clubs to get Flanders by offering a six-year contract, while outbidding Collingwood and the Western Bulldogs for Silvagni. The intent is crystal clear. 

"I'm a fan of it," Montagna said. "Whether it works or not, time will tell. I think the club and other clubs are realising that if you want to be competitive, you have to be ultra-competitive in trade and free agency. 

"The only advantage that some of these clubs have that aren't at the top of the ladder or aren't a big marquee club is to pay big money. As long as they've planned for it, and it's not something they've shot off the side of the hip at, which St Kilda has planned for, it's been a well executed plan. The club will give it a go and if it doesn't work then at least they’ve had a crack."

Tom De Koning poses during St Kilda's 2026 team photo day at RSEA Park. Picture: AFL Photos

Montagna will be at the MCG on Sunday night calling the game for Triple M. Breen will be watching on from the Olympic Stand, alongside Stewart, who will make a rare appearance to celebrate a milestone that becomes more significant with each passing year.

"I'm not a big reunion guy," Stewart confessed. "I have enough internal reunions. But I do like to see the players when we do meet. I'm really looking forward to Sunday night."

St Kilda waited 69 seasons to win its first premiership in 1966 and now holds the longest active drought. The Western Bulldogs ended a 62-year wait in 2016, while Melbourne broke a 57-year drought in 2021. Is this the year for long suffering Saints supporters?