One of the blockbuster deals that fell through in the final hours of the 2025 trade period was Collingwood's failed attempt to poach contracted captain Jy Simpkin from the North Melbourne Kangaroos, who has reportedly become disgruntled with his changing role under senior coach Alastair Clarkson.
The Kangaroos wanted two first-round selections for their skipper, setting the bar high for a two-time best and fairest winner. The Pies had tabled its 2027 first-round pick for Simpkin and Pick 46, which was quickly rejected, before offering a future second-round selection.
According to Collingwood list manager Justin Leppitsch, the deal was unable to be completed as North Melbourne opted not to follow the precedent set by a trade Collingwood completed in 2023, which occurred under similar circumstances.
"Jy Simpkin was an interesting one. From their perspective, it's their captain, their leader," Leppitsch said on AFL Trade Radio on Thursday.
"It goes back to value.
"We had Taylor Adams leave us a few years ago. He was a midfielder that got kicked out of the square to half-forward, and we traded him for Pick 33."
Adams requested a trade after missing out on Collingwood's 2023 premiership due to a lack of clarity around his role, even while being the club's vice-captain at the time.
Leppitsch noted that Collingwood's tabled offers went above and beyond the Taylor Adams deal too, highlighting Simpkin's younger age (27 years old to Adams' 30 years at the time of trade) and his important role at Arden Street, both on and off the field.
"The Kangaroos rate Jy's leadership and what he brings, and I get that. There's no criticism of North Melbourne at all, it's just that we had our parameters as well," Leppitsch said.
"He was coming to us to fill our long-term needs. We saw him as a guy that could get that steady stream of replacement without having to rely on our 18-year-olds too much.
"That would've been his purpose and would've been great to have, but the club wasn't willing to go to that level [two first-round picks] to do that."
The capitulation of the deal means that Collingwood has been unable to bolster their midfield depth this trade period, despite heavily pursuing the likes of Simpkin and Clayton Oliver, while Simpkin likely returns to North Melbourne without the captain tag next to his name.
