On April 25 last year, the 21-year-old went to a dawn service in Perth and paid his respects to two great uncles, who returned from World War II with serious injuries.
In front of 2607 fans that afternoon at Good Grocer Park, May kicked three goals for Subiaco in their WAFL loss to home side East Fremantle.
On Saturday, he will play his first AFL Anzac Day game for Essendon against Collingwood at the MCG. The crowd this time will be somewhat bigger.
"It's been a massive year. I'm really looked forward to this Saturday ... to play in front of 90,000 fans," May told AAP.
"It's more the occasion I'm excited for, to represent people who have fought before us."
Everything changed when the Bombers picked him up in last year's mid-season draft, after he had been linked to the Magpies.
The key forward signed a two-year contract extension earlier this month, taking May through to the end of the 2028 season.
He'd ended up at Subiaco after two years in the Richmond VFL program. After so much big change, May is keeping his mindset deliberately narrow.
"At this point, it's just focusing on my role each week rather than the bigger picture, that's held me in good stead," he said.
"To play this week on a massive occasion, Anzac Day, it doesn't really get much bigger than that, other than finals.
"I'm absolutely loving my time at Essendon, I think we're building something really special ... I genuinely mean that."
May has played 12 games for the Bombers, but their losing streak meant he had never enjoyed a win until Gather Round and the morale-boosting success against Melbourne.
"It was a long time coming, but to finally get the result we were after - we don't go out there to not win," he said.
"So to finally get that result was an awesome feeling. You bottle it up and chase the next time you run out.
"We had the belief going into the season. We put in a massive amount in and we were really confident going into round one.
"The first four rounds didn't go our way ... in saying that, we didn't lose belief at all. (The win) solidified we're on the right track and justified that confidence."
Essendon backed that up with a narrow away loss to Gold Coast and will fancy their chances against Collingwood, who remain without captain Darcy Moore.
But the Magpies will start favourites. Over the last two decades they have a 14-4 record on Anzac Day, with one draw.
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