Wingman of the Finals 2025 – Ollie Dempsey

You guys know me by now – I’m like a duck.

No, no… my fellow writers’ wives are okay, I swear. A duck… not The Duck.

Anyway, while I’m looking serene (and devilishly handsome), as I float atop the pond that is the AFL Finals, your old pal HB, who according to some is not the same as he used to be, has been paddling away furiously under the surface to organise two special awards for the finals, as additions to our regular season awards.

The other will come when I finalise the last set of numbers and add in coaches votes, but the first has been run and won.

It is a bittersweet result, as the winner is the man who snagged seven goals for the Cats over the course of the finals, to lead his team, but ended up watching the Lions overrun them.

And he did it from the wing.

Ollie Dempsey has become a master of the art of scoring. Teams don’t seem to learn when it comes to playing him tightly, as he simply cannot be left alone anywhere near the defensive fifty.

He was arguably the best player on the park in week one of the finals, as he snagged three goals and had 25 touches against the Lions. After a quieter game against the Hawks (with the best defensive wing in the home and away season, Massimo D’Ambrosio, playing on him), he made the most of his junk time opportunities to finish with four snags in the Grand Final.

Seven goals across three finals without even playing forward… not a bad result for the young man.

Should junktime stats count?

They do in this case, and in the end, it was enough to elevate Dempsey into the number one position and take out our first Wingman of the Finals Award.

I haven’t added a name to this award, as I don’t like to do that without permission of the player, or in the case of a player who’s passed, their family. As such, it’ll remain as is for the time being.

Personally, I’d love to call it the Peter Matera Wingman of the Finals Award, so if anyone knows him, please pass on my details.

Here’s a rundown of the placings.

 

1 – OLLIE DEMPSEY

2 – JARROD BERRY

3 – CALLUM AH CHEE

4 – JACK CRISP

5 – MASSIMO D’AMBROSIO

 

This was closer than you’d think.

Dempsey’s goals obviously stand out – they always do. But there is more to being a great wingman than just the offence. That’s just the part of the game people get caught up in.

Jarrod Berry, despite missing the Grand Final, was very close to pinching the award. I suppose, in the end, they played three games apiece, so it is a level playing field.

He plays a more rounded role than Dempsey. He had 11 rebound 50s, working back defensively in his three games, whilst Dempsey had two. He also had him covered for inside 50s, as well as metres gained.

That’s why it was close. Dempsey is exceptional at finding ways to snag goals. In that regard, he is a player that definitely moves the needle. In other facets… not so brilliant. However, if he adds those strings to his bow in the coming season, he will be close to unstoppable.

I used a scoring system very similar to our home and away version, but tweaked it slightly to make it more finals-friendly.

In the end, with both playing three games, Dempsey scored 169.9 points.

Berry, had he played in the Grand Final, would have likely won it with the additional game under his belt. He finished with 164.2 points.

The next best failed to crack 70.

And so it was that the first-place and second place in the 2025 Robert Flower Wingman of the Year Award switched places in the finals, with Dempsey’s offence too much for Berry after he was injured in the Prelim.

Do both these guys line up on the wing in 2026? Or do their respective coaches have other plans? The sands shift swiftly, season to season (hmmm, sounds like a tongue twister) and, as always, The Mongrel Punt will be covering just who is the best in the role all season long.

 

As always, massive thanks to those who support this work. You can see the amount of care that goes into it. I love footy, I love writing about it, and I hope you enjoy reading it. Without you, this whole thing falls over. Sincerely… thank you – HB

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