St Kilda president Andrew Bassat sidled up to Josh Battle late in the 2024 season and asked if there was more the club could do in its bid to re-sign the exciting free agent.

Battle’s reply was that at Hawthorn as soon as families arrived on game day a club staffer would be on hand to help babysit the children of players.

By the next week Bassat had put in place the kind of creche system that St Kilda now calls a match-day concierge to integrate family and partners into the game-day experience.

Yet as Battle’s decision dragged on, Hawthorn remained ahead of the game.

The single disadvantage Hawthorn knew it was up against – their refusal to pay Battle more than St Kilda – turned out to be their secret weapon.

Sam Mitchell and wife Lyndall had wooed Battle and wife Casey for months even as he made clear to Hawthorn his reservations about re-signing at St Kilda had nothing to do with Ross Lyon’s coaching.

Hawthorn had shown off their new Kennedy Centre headquarters build at Dingley, and had preached how integral joy is to everything they do.

Mitchell and football boss Rob McCartney had told him he would be a key backline role member but not the hero under pressure to win matches off his own boot.

As part of their full-service pitch (lifestyle, finances, on-field, off-field, family, enjoyment, post-career) they had shown him exactly how he could grow that six-year contract of nearly $5m into a nest egg that would set him up for life.

Then came the kicker.

They predicted exactly what St Kilda would do next – try to blow them out of the water with a last-ditch deal.

That final St Kilda revised deal came like clockwork – at $900,000 a season well above the Hawthorn offer – in a bid to either re-sign him or force Hawthorn to match and guarantee first-round compensation for the Saints.

For Battle, signing on for all the right reasons instead of the fat paycheck just seemed right.

The Hawks had him hook, line and sinker and didn’t even have to lift their offer.

And St Kilda …

They had missed out once again.

THE MISSION

St Kilda’s mission to turn itself into Destination Moorabbin is easy to mock.

After all, the outrageous sums they offered Giant Finn Callaghan – without him even meeting the coach – represented yet another swing and miss.

The long list of rejections as prospective AFL partners swiped left instead of right is reminiscent of North Melbourne’s failure rate this past decade.

Jordan De Goey, Hugh McCluggage, Tom De Koning (in 2023), Sam De Koning, Zach Merrett, Karl Amon, Jacob Weitering, Andrew Brayshaw and more have all failed to respond to St Kilda’s wooing.

Yet the Saints won’t die wondering as they chase a quartet of rival players while simultaneously overhauling its entire approach to securing rival talent.

The next six months might just represent the most important period of Ross Lyon’s second incarnation as St Kilda coach.

Can the club prove to its list of targets it has changed then land the key back, ruckman and midfielder it believes will round out its premiership build.

Or will it wallow in mediocrity forever?

St Kilda has ambitious plans – to continue its overhaul, to bolster its father-son academy, to embrace its past players like never before, to become the best team at recruiting Indigenous talent.

And above all else, to position itself to win that second premiership.

Yet until it can round out its four years of relentless drafting by actually landing that big fish, the questions over its destination status will remain.

THE TARGETS

St Kilda’s chase for Tom De Koning is real and it is extraordinary.

The money, as reported by this masthead in December, is as much as $1.7 million across seven seasons, dwarfing Carlton’s offer of just over $1 million a season in the same tenure.

Carlton says it cannot lift its offer any more, but it said this two years ago amid the kind of TDK hot streak that is embarking upon again.

Having been criticised for simply calling up managers and offering huge sums in a move reminiscent of the ‘Wild West’ style days of AFL recruiting, the Saints have moved with the times.

This masthead understands coach Ross Lyon has been intimately involved in discussions with potential free agency and trade targets.

He has watched on while Sam Mitchell’s charm offensive won over his targets and made players like Docker Liam Henry briefly reconsider whether they were St Kilda bound with his charismatic pitches.

One footy agent said the Saints had finally upped the game on their pitch to free agents, out-of-contract stars and those in contract looking to escape their current clubs.

“They have got a proper plan in place … and it’s real,” he said.

“They are being very calculated with it now. The plan isn’t solely about money. I don’t think players look too much at the off-field stuff, it is more about what is going to happen on the field.

“The coaching (side of things) is important; where the list is at is really important.”

The issue with De Koning?

Are there two more incompatible ruckmen than Marshall and De Koning to play in the same side given both demand huge game time in the middle to thrive?

St Kilda offered the world to Port Adelaide defender Miles Bergman two seasons ago and to his credit he stayed the course at Port Adelaide.

Yet this time around it would be surprising if St Kilda didn’t get their man.

Bergman has told his Melbourne footy and school mates of the strong pull from home and has already put off talks with the Power until the mid-season break.

The St Kilda pitch is about midfield time and a return to the bayside suburbs he called home as a former St Bede’s College student.

Even Port Adelaide insiders don’t really know what makes Bergman tick, but he has made it clear that his football career is a part of him but not the only or even main element.

Family, friends and interests outside of the AFL are just as important, all of which are easier to satisfy in Melbourne, which is why a return to Victoria seems so likely.

Long-time recruiting figures are split on whether he could play as a pure inside mid but with his elite running power and rangy figure (189cm) he could easily settle on a wing.

Bergman is a huge Ken Hinkley fan (Josh Carr is the midfield coach so he has not coached a line that involves Bergman) and sources suggest he has already confided in the senior coach about his openness to a move home.

The official line from those close to him is that he isn’t even close to making a decision but if the Saints cannot lure him home given all the positives of a move, it would represent a real blow to their strategy.

At 23, the No. 14 draft pick from the 2019 national draft would be in the perfect age bracket even if he is another flanker instead of a pure inside mid.

What the Power does know is that he has never been interested in being the highly marketable star who steals the limelight.

So if he could be one of a number of players joining St Kilda rather than the ‘star signing’ it would help the club’s cause.

Every Victorian club is interested in GWS defender Leek Aleer, but rivals believe St Kilda would trump them all if it came to a bidding contest.

Figures of as much from the Saints as $800,000-$900,000 a season have been bandied about for the Kenyan-born, Sudanese-heritage defender, extraordinary given his eight AFL games last year saw him averaging only 10 possessions.

But everyone saw that breakout game against Geelong – six intercept marks and 11 intercept possessions – and GWS is resigned to losing the uncontracted key defender.

He is stuck behind Sam Taylor (contracted to 2032), Jack Buckley (2026) and Connor Idun (2032) and would play in every other defence in AFL football.

Leek’s manager Dylan Smith, of Centimeter Perfect, is in Sydney on Tuesday to talk to the GWS defender about his future.

The Adelaide-raised Aleer is intensely loyal and loves Sydney but knows he might need to move to play regular football.

Smith’s other client Alix Tauru has settled in well as a top 10 pick at St Kilda and absolutely loves Lyon, which can never hurt the Aleer pitch in an industry where clients from the same management firms often speak among themselves.

Luke Davies-Uniacke wanted the Roos to prove to him that they were ready to compete and after last week’s win over Melbourne, he looks set to knock back St Kilda’s monster offer.

THE CHANGES

An internal club dossier on St Kilda’s playing list, which this masthead has seen, details the growth in the playing group across the past few seasons.

But it also hints at the subtle – and none-too-subtle – changes that have been made to make the club a better and more attractive proposition.

One of the key ‘takeaways’ listed centres on the theme ‘We’re younger than people think’, detailing how they have transformed from the second oldest list in 2021 to the equal third youngest last season.

Before picking up Harry Boyd – who turned 27 in February – as an SSP earlier this year, the 2025 Saints had a similar age profile to Richmond.

But the list analysis goes even deeper.

In 2021 St Kilda had players aged 21 and under who played a collective 61 games; it was 53 a year later.

In 2023 the Saints had the most games of a 21-and-under cohort of any team to play finals in 15 years, with 109 games. It was up to 134 games last season.

But the Saints have also prided themselves on remaining competitive throughout the evolution.

Lyon has driven some key directional changes which the club believes will stand it in good stead deep into the future.

One is a desire to have one of the best First Nations programs in the AFL system.

The Saints currently have six First Nations AFL players – second in the league behind Gold Coast in numbers – with Isaac Keeler becoming the latest Indigenous debutant for the club in last week’s win over Geelong.

The club now has a dedicated Yawa (which roughly translates to journey) room at Moorabbin where the portraits of every First Nations AFL and AFLW player to represent the club is displayed.

Keeler’s image is the most recent.

The Saints have also invested heavily in sourcing talent from Ireland, something which came to the fore last Saturday night when second game County Cork graduate Liam O’Connell took one of the game-saving marks to sink the Cats.

County Meath teenager Eamonn Armstrong, a Category B rookie, will join the club mid-season when he finishes his schooling in Ireland.

Lyon, so often considered tough and uncompromising in his demands on players, has more recently championed the cause for fewer working hours inside the club.

He said recently that players spend about 16 hours per week at the club, excluding game days, but the flip side to that is that he now demands every player on the list either works or studies in their time away from the club.

Some players run businesses; most study a range of courses from business degrees to carpentry courses.

But everyone has to do something.

The match-day concierge – a Bassat initiative – sits with families during the games and caters for any issues that crop up from babysitting to ticketing to access.

St Kilda will never have the advantages of Geelong – with the Surf Coast lifestyle – or Collingwood’s mega-brand appeal.

But the point of the makeover is to not be beaten before they start with their pitches to rival players.

WHY HAS ST KILDA MISSED OUT SO OFTEN IN THE PAST?

In 2016 North Melbourne offered Isaac Heeney a massive multimillion-dollar offer that he was always going to refuse amid what seemed like a dozen embarrassing knockbacks at Arden Street.

St Kilda’s past recruiting endeavours under its list team of Steve Silvagni and veteran football identity Graeme Allan have too often replicated this kind of take-it-or-leave it approach.

As one ex-Saints star says of the old-fashioned approach, often it doesn’t work in an era when clubs start their pitches 18 months out.

Increasingly bringing a player’s partner along for the ride and making her fully invested in the decision is just as important as an increase in a fat pay cheque that might pay for the house renovation or new car.

Says one rival list boss of the big unannounced offer that included a mega-deal for Carlton’s Jacob Weitering which was knocked back: “It feels scattergun. Everyone loves ‘Gubby’ and ‘SOS’ but they feel like a club in a hurry rather than a club that builds themselves up slowly”.

Rivals cite the decision to offer Carlton swingman Brodie Kemp a four-year deal on the last morning of the trade period – having never thrown up his name before – as an example of that strategy.

In the end Carlton would have let go of the former pick 17 for a second-round pick but the Saints went cold when they couldn’t get him for a later selection.

As a feared recruiting presence, Allan could get most players he wanted in previous decades at Collingwood, Brisbane and GWS, with an extra $300,000 on a contract when it doubled a player’s wage.

But offering a star already about to secure $1 million a year $1.3 million is no longer a game-changer.

Another list expert says player managers know putting a midfielder into St Kilda means their client would be on a hiding to nothing, given the lack of depth within the Saints’ on-ball brigade.

Case in point – Saints captain Jack Steele was eviscerated on the Monday night shows for a defensive effort against Jordan Dawson in round 1 but Will Day was well-beaten on the same weekend and no one blinked an eyelid because Hawthorn won.

You want to go to a club where you think you have a chance of having success, and it’s hard to go to St Kilda and think you have a chance of having success, said one industry figure.

He highlights the Hawthorn example – build through the draft until rival players can see the improvement ahead.

“The reason Hawthorn got Barrass is because they drafted (Will) Day and (Connor) Macdonald and Nick Watson and Josh Weddle. They found Jai Newcombe. St Kilda is trying to build without proving they are there yet. They have got some good players but not enough. And Mason Wood and Brad Hill will be gone by the time they are good.”

THE MESSIAH COMPLEX … AND THE SAINTS’ HARDEST SELL

One key footy industry insider insists there has been a big change in the player movement space across the last decade or so, which might explain St Kilda’s inability to hook one of footy’s biggest fish with mind-boggling offers.

He refers to it as ‘the Messiah Complex’.

Players from past generations might have been more willing to deal with the scrutiny, expectation and pressure of being pitched as the multimillion-dollar potential saviour to a football club down on its luck.

Think Gary Ablett Jr. to Gold Coast.

Or Chris Judd to Carlton.

Or even Buddy Franklin to Sydney.

Or even earlier, more than four decades ago, Peter Moore and Kelvin Templeton who moved to Melbourne on the biggest deals in footy.

None of those players won flags at their new clubs, and only Franklin made it to a grand final at his second club.

But this footy insider says it is now less palatable to chase cash in the modern 24/7 footy cycle with the explosion of social media given if it fails it will come back on your head.

“The money (St Kilda) is offering is real,” he said.

“I think $1.7m (per season is right), but I think more and more the players themselves don’t want to come as the Messiah and say ‘I have got all this money and it is up to me to save them’.

“It’s not what happens. You need 20 others to (be a successful side). It is a bit like Carlton at the moment. They have got four or five really good players and everyone says they have got a good list. But (too often) it is down to those good players (whether they win or lose).

Finn Callaghan made clear that arriving at St Kilda as the messiah was the last thing he was interested in, even if he believed they might win a flag at some stage.

Which he didn’t.

St Kilda’s past history might also be proving an impediment, given the club has famously won one premiership by one point in almost 130 years in the competition.

Asked what remains the most challenging aspect for St Kilda in chasing high-end talent, one footy industry source said: “I think their hardest sell is that they have won one flag in more than 100 years. How do you convince someone that you can change that?”

CAN ST KILDA KEEP NASIAH WANGANEEN-MILERA?

Rival clubs will offer Nasiah Wanganeen-Milera the world to return to South Australia.

And St Kilda will have to pay well over $1 million a year to match those deals.

Yet all is not lost.

He is coached by the brilliant Corey Enright, he loves the joint, he has many Indigenous teammates he is close to and he is carrying on a family tradition after his stepfather Terry played 30 games for the club.

In his second season he had re-signed by April until the end of this year in an indication of his happiness.

If he left now it would be to cash in and be closer to home rather than because he is homesick.

But his management would be doing him a disservice if they didn’t maximise his worth by making clear that if Callaghan is worth $1.7 million, he’s not far short.

He could sign a four-year deal at St Kilda to free agency or the mega-deal that would lock in his future for 6-8 years.

St Kilda is open to a short or long-term deal but at this stage hasn’t offered the kind of contract that would get him to sign in the near future.

He is arguably the Saints’ best player and he also has to assess if he will maximise his career at a rebuilding club or one like Adelaide or Port Adelaide much closer to the premiership window.

Wanganeen-Milera departing would be a crippling blow to what St Kilda is building but the club has two key factors in their favour.

He wants to stay, and St Kilda has as much cap space as anyone to keep him.

St Kilda is already pushing to extend Tauru – he isn’t in a hurry – but as Lyon says the young Saints are signing on.

Max King is locked in to 2032, Mitch Owens to 2029, Jack Higgins to 2029, Lance Collard to 2027.

IS ST KILDA STILL STUCK IN THE MIDDLE GROUND

There are some St Kilda identities who urged the club to do whatever it took to chase the second flag instead of remaining stuck in the doom loop of 8th-12th finishes before Ross Lyon took over.

As Bassat sacked coach Brett Ratten, moved on CEO Simon Lethlean and brought in a new recruiting team, he was also urged to be even bolder.

Why not actually bottom out and put Jack Steele, Rowan Marshall or even Max King up for trade to get the kind of elite draft hand that Richmond possessed last year?

What Lyon will have to prove is that St Kilda can enter the premiership window without any picks inside the top eight apart from the injury-prone King.

Wins like the rousing victory over Geelong – full of Ross Lyon-style effort and commitment – inspire the fan base.

But when the club is relying on Zak Jones to turn back the clock and Marshall to put the superman cape on, will eking out another 10-win season progress those flag ambitions?

Lyon was fully justified in trying to test the list’s capabilities in his first year before a finals thumping against GWS but in hindsight it achieved little apart from devaluing that season’s first draft pick.

Former St Kilda coach Grant Thomas continues to watch from afar, desperate to see success but unsure if it is coming with the current list.

“Too many things sort of happen that you just have to read the tea leaves and think we haven’t got things exactly right,” Thomas said.

“Great clubs make great decisions and usually generate successful outcomes. For whatever reason we have a few problems in doing that.

Lyon is beloved by his players and is much better at blending the pats on the back with the verbal shirt-fronts that saw him strip players down to size in previous coaching stints.

He delegates, he cares, he invests in his players and they repay the investment.

They genuinely seem to love him where in past stints there was a cohort who might have played to prove him wrong.

But the St Kilda culture is still a unique one where his aura is massive.

Assistant coaches know not to turn up a moment late; in meetings Lyon is very much the most important man in the room.

He rides staff hard – he is all about accountability – and those outside the key areas of trust can at times feel left out.

But that is the Lyon way. As one insider said: “this is Ross’ club.”

It is in his DNA and turning into soft, cuddly Ross 24/7 would remove his defining characteristic that has proved so successful in building Grand Final teams.

Recontracted for 2027, he might never win the elusive second flag.

But if he eventually becomes the rebuilding coach instead of the one who cashes in he will leave having set up the club with solid foundations.

They have elite facilities, strong leadership, and have put their chief focus back into football.

THE LIST BUILD

It was a risky top-up strategy across the 2019 and 2020 trade/free agency period that bit deep into St Kilda’s draft currency.

Nine players from rival AFL clubs came in over that two year period, which left only four picks available in two national drafts (none of them inside pick 25).

Only one of those draft picks, Ryan Byrnes, remains at the club.

One key football person said clubs chasing a successful rebuild, or restructure, needed at least four drafts to get it right.

The Saints have made good inroads on young talent since taking Nasiah Wanganeen-Milera with pick 11 in 2021 in a haul that included NGA players Mitch Owens (31) and Marcus Windhager (47).

The following year they took Mattaes Phillipou (10), and with their last pick of that 2022 draft brought in Indigenous talent Isaac Keeler, who made his debut last week.

Darcy Wilson was selected at pick 18 in 2023, while the club went for defenders Tobie Travaglia (eight) and Alix Tauru (10) with high-end selections last November.

Bassat said in a recent newspaper article that Phillipou and Wilson would go vastly higher if their drafts were reordered but rivals aren’t so sure.

Phillipou would jump above Jhye Clarke and Reuben Ginbey in the 2022 national draft but that draft was stacked with elite mids – Will Ashcroft, Harry Sheezel, George Wardlaw and Cam Mackenzie.

Lyon had to test out the list’s capabilities as they made finals in 2023 instead of bottoming out but it cost them a mid like Harley Reid, Colby McKercher, Caleb Windsor, Ryley Sanders or exciting small like Nick Watson.

Footy analyst Mick McGuane said there was a lot to like about the way the Saints had gone back to the draft since the Covid years.

But he worries about the speed of older midfielders, including skipper Jack Steele, and their capacity to play alternative roles.

“There’s growth in their youth,” McGuane said. “But in my opinion, the kids are not the issue.

“Wanganeen-Milera is a star.

“Phillipou will be a very good player. He can play that Dustin Martin prototype mid-forward role. He is not there yet, he has some work to do.

“They will nurture Wilson. He is an outside player now but he will become that inside mid!

“It is all about their evolution as players to go from a running back to a midfielder because they have the attributes to become midfielders.

“You look at the speed and class they can bring. You can have your bash and crash mids but like we have seen at Carlton, it just doesn’t get the job done, so the Saints need these young guys in there.”

There are problem areas – Caminiti has shown signs in defence alongside the brilliant Callum Wilkie but at times when second-year defender Arie Schoenmaker and Zaine Cordy are under siege it is hard to see it morphing into a premiership defence.

In round 1 as Steele battled alongside Hunter Clark and Jones, while Jack Macrae racked it up it was obvious St Kilda had some serious midfield deficiencies.

Then, a week later, against Geelong, Jones turned back the clock from the wing, Macrae hit leading forwards laces out and Steele regained the pep in his step.

Liam Henry returned through the VFL and Travaglia was dominant in the VFL.

Add another top 10 draft pick as a young mid, turn Bergman into a midfielder, get Henry injury free and there is a path forward which might just prove the difference.