Saints die – almost by definition. Saint Lawrence was said to have been grilled on a gridiron. Saint Bartholomew was flayed alive. Saint Sebastian, meanwhile, was unlucky enough to purportedly be killed twice. (Only canonised once though, innit.) The experience of supporting the St Kilda Football Club has tended to tread a similar path – meekness, suffering, dubious gratification. No more. The Saints aren’t content with living and dying meekly anymore. In the recent trade period, and the months preceding it, they’ve chosen a different approach, one which sharply diverges from the one they’ve pursued since 2021, and indeed one that’s rarely associated with the club: audacity. It’s a challenge to conventional wisdom of how to build a competitive AFL list. It’s recognition of the narrow path the club must walk to find success. And it’s a demonstration of the extent to which one player will define their prospects for the rest of the decade.
Let’s quickly summarise. Four players joined the Saints in this year’s trade period. Tom De Koning and Jack Silvagni as free agents from Carlton, Sam Flanders from Gold Coast in exchange for Pick 7, and Liam Ryan from West Coast for St Kilda’s 2026 second-round pick. Fringe ruck Max Heath and captain Jack Steele both departed for Melbourne. Steele’s exit wasn’t a big surprise – a parting of ways had been rumoured for some time – but St Kilda accepting just a 2027 third-round pick in return probably was. (Tangentially: what’s with so many club captains wanting to leave?) The moves St Kilda didn’t make are equally intriguing. Despite De Koning’s arrival, incumbent ruck Rowan Marshall stayed put. The best argument I heard made for the De Koning move – and his eyebrow-raising salary – was that it would clear the way for Marshall to move clubs in exchange for something like a late first-round pick. In doing so, the Saints would have effectively traded salary cap space (a resource they had in abundance) for an extra draft pick (which always comes in handy). However, despite Geelong apparently making a late offer of their 2025 first-round pick and a future second-rounder, Marshall will remain a Saint – even if he probably won’t be the number one ruck. Saints fans and coaches will hope that both he can show more acumen as a forward than he’s displayed thus far. Then there’s Leek Aleer. The defender’s move to Moorabbin had been considered a fait accompli for months. But St Kilda’s successful pursuit of Jack Silvagni rather changed their thinking, leading them to withdraw their interest. It was a reminder of how ruthless clubs can be.
This flurry of activity represents a sharp pivot from the list management strategy St Kilda appeared to be pursuing. Since 2021, the Saints had used 19 picks in the national draft, four of which came in the top dozen, and only spent picks on three traded players (Paddy Dow, Liam Henry, and Jack Macrae). But, despite their drafting yielding some good players (and one great one), it hasn’t translated to the sort of success that supporters and club officials wanted. Promise, but no real progress. The shift in strategy has a single catalyst: their superstar Nasiah Wanganeen-Milera’s choice to re-sign for only two years. St Kilda interpreted that as a message: surround me with a team that can win, and I might stay beyond 2027. Hence the splurge on De Koning, Silvagni, Ryan and Flanders. The aim appears simple: win enough games and show enough progress in the next two seasons to convince their superstar his future belongs in red, white, and black.
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But that, naturally, raises a question without as clear an answer: what does success look like to Wanganeen-Milera? A Premiership is every player’s dream, but that’s a cruel benchmark for St Kilda. A more realistic one might be winning a final, with clear signs that improvement is being driven by young players. That would prove direction and ambition; the intangible things that make any workplace worth staying at.
Clearly, changing strategies because of a single player is a major risk. It’s possible that Wanganeen-Milera’s actual desire this year was to leave for a South Australian club, but that his club of choice didn’t have the draft capital to satisfy the Saints. If so, this might all be futile – because it would suggest that Wanganeen-Milera’s definition of success can’t be met by St Kilda (at least as long as they’re based in Victoria). But the risk is rational. Wanganeen-Milera is St Kilda’s best draftee – best player, full stop – since Nick Riewoldt. He is the hardest kind of player to find; a bona fide match-winner who has yet to enter his prime years. And doubling down on doing almost anything they can to keep him suggests that the people who call the shots at St Kilda have grasped something essentially correct about their predicament: they need to take risks other clubs might find imprudent. Club president Andrew Bassat knows this. Many people interpreted his broadside at the northern state clubs, and their embarrassment of academy and father-son talents, at last year’s Best & Fairest awards as the bitterness of a man who had just lost his second-best defender to free agency. Perhaps it was that. But I interpreted it as a recognition that the draft alone won’t save the Saints. Building through it is getting harder, and St Kilda must make their own luck.
Luck isn’t something the Saints have historically had in abundance. They lack father-sons, academies (although their Next Generation Academy has yielded some talent), and a tradition of winning. Based on what’s been reported about the salaries of De Koning, Flanders, and Silvagni, they’ve had to pay higher-than-market rates to secure their trade targets. But for the first time in 15 years, they have something priceless: a player every other club covets. The AFL isn’t like the NBA. One star can’t carry a team to glory. You need depth, versatility, and a distribution of quality across the field. But transcendent players like Wanganeen-Milera can create momentum. Players at other clubs might consider the Saints in a way they hadn’t previously. Talented players could re-sign for below-market rates. Wanganeen-Milera’s choice to re-sign arguably already has yielded some dividends – Marcus Windhager’s choice to re-sign was apparently driven in part by his housemate’s choice to do the same. I’m sure Tom De Koning, Liam Ryan, and Sam Flanders are all excited by the prospect of playing with one of the most exciting players in footy. The club is clearly of the view that Wanganeen-Milera holds the key to its medium-term future, both on and off the field. It’s hard to disagree. Seen in this light, what looks superficially like a reckless all-in bet becomes something else: the only logical play.
Taking every reasonable step, and even some unreasonable ones, to keep Wanganeen-Milera, is rational. But that doesn’t mean it’ll work. The players St Kilda have brought in during this trade period won’t make them Premiership contenders. Frankly, I’m sceptical they’ll even make the Saints a finals side. There were nine good teams in 2025. Sydney and Port Adelaide, preliminary finalists just last year, will both believe they can bounce back after disappointing seasons. Will St Kilda be better than any of those 11 sides, especially given the broad error bars around Max King, Phillipou, and as-yet unresolved questions about their ruck corps? But here’s where I think that most observers and St Kilda are having different conversations. Instead of asking whether St Kilda will play finals in 2026, we should be asking: is St Kilda’s attempt to demonstrate their ambition to keep Nasiah Wanganeen-Milera and surround him with quality more likely to eventually yield success – the sort of success that convinces him to sign a long-term deal – than doing things the way they have been (building through the draft, losing players to more putatively attractive clubs, and constantly resetting the clock)? I think it probably is. Because the reality is they weren’t on the trajectory that ended in them retaining Wanganeen-Milera past 2027. And right now, if there’s no Nasiah, there’s no party.
Understanding risk requires looking at counterfactuals and opportunity cost. In the subtitle to this post, I wrote that the Saints are applying the Costanza Method to list management. I wasn’t joking. St Kilda’s drafting has produced one superstar and too many maybes. If there are moves you can make to leverage your prime asset – and avoid selling him for an unsatisfactory price in two years, setting back the entire list build, and disappointing supporters anew – you make them. St Kilda’s pivot might fail; it probably will. But a bad outcome isn’t the same as a bad process. For a club long defined by martyrdom, that’s progress in itself. If the Saints are doomed to die again, at least this time they’ll die trying.