Halloween night, 1998, and while the rest of Australia’s best young footballers were kept sleepless ahead of the next day’s AFL draft, 17-year-old West Australian Des Headland could rest peacefully – he knew exactly where he was headed.

A strong season of senior footy with Subiaco in the WAFL had the pacy midfielder-forward tipped as a top pick, and despite an underwhelming national Under 18s carnival, the Brisbane Lions were sure he was the right player to take with the first selection.

“I met up with Brisbane the night before for dinner and they virtually said they were going to take me at number one the next day,” Headland says.

“It was a bit of a surreal feeling. Obviously a lot of the boys go to the draft and don’t know where they’re going. It sort of took that excitement – I was definitely excited, no doubt about it – but (it took) the unknown out of it.

“Knowing helped me get my head around it a lot quicker than other boys did.”

Fast forward one year later to 1999, and there is a lot less certainty about Josh Fraser, sitting with his father at Melbourne Park.

Although he was hailed as “everyone’s first choice” on the telecast by AFL Draft guru Kevin Sheehan, the 17-year-old from Mansfield in country Victoria looked relieved when his name was read out as pick one by Collingwood.  

Speaking to the The New Daily 14 years after the fact, Fraser insists he had nowhere near the level of certainty Headland was given by the Lions.

“As far as any commitment or anything like that, there really wasn’t any from Collingwood’s part,” he says.

“I don’t even think I went through the interview process with Collingwood at the draft camp. I had a chat to Fremantle from memory, and that was it.

“It was probably in the lap of the Gods a little bit. I know Fremantle had two or three early picks inside the top five or six, so obviously my preference at that stage was to stay in Victoria.”

While Headland and Fraser were at the top of Australia’s talent pool, former Hawthorn skipper Richie Vandenberg’s draft-day experience could not have been more different.

Last chance saloon

Unfancied as a teenager, it looked as though the opportunity for an AFL career would pass Vandenberg by until he was thrown a bone by Carlton coach David Parkin in 1996.

“At the end of the ’96 season, heading into the ’97, I actually did a pre-season with Carlton and was put onto their supplementary list,” Vandenberg says.

“David Parkin asked me to train at Carlton for that season, ’97, but I went back and played at Uni Blues.

“I thought the main (draft) interest was going to come out of Carlton at the end of ’97, then lo and behold Hawthorn, who’d had some contact with me, bobbed up and that’s where I ended up.”

Vandenberg was taken with pick 78, and had been so blasé about the whole experience he neglected to front up for the event.

“I remember sitting in the lounge room when I got the news,” he says. “I was sitting at home in my terraced house in Carlton studying for (engineering) exams. I hadn’t written it off (an AFL career) because I probably never had my expectations up.”

Vandenberg battled injury early in his career to become a regular with the Hawks, and was revered by the brown and gold faithful – so much so that when Alastair Clarkson joined the club for the 2005 season, he asked Vandenberg to lead the side.

“It was unexpected. It was an amazing honour,” he says.

“While you’re living the moment you probably don’t appreciate what it means. I was just focused on doing the best job I could for the club at the time.”

A flag won, a flag lost

Headland’s arrival in Brisbane coincided with the inauguration of coach Leigh Matthews, and the start of the Lions’ golden era.

After missing out on being chosen for the 2001 premiership side, he made up for it the following year when, as a 21-year-old, he was part of the Lions’ team to win back-to-back flags.

But the pull of a return home the Western Australia proved too strong. He opted for a trade to Fremantle for the start of the 2003 season.

“I had a young daughter and my wife was pregnant at the time, so we decided to make the move back to Perth to be around our family and friends,” he says.

Although his move to Fremantle stung the Lions at the time, Headland says he was embraced by the club at this year’s 10th anniversary of the ‘three-peat’ side which won flags from 2001-2003.

“It was fantastic to go back and be recognised as a premiership player. The footy club welcomed me back with open arms,” he says.

That 2002 premiership is something Headland, who was forced to retire at 28 with a degenerative knee problem, holds dear.

It’s a balm neither Fraser nor Vandenberg can use to soothe reflections on their own playing days.

Fraser had fallen behind Darren Jolly in the ruck pecking order at Collingwood for their 2010 flag, while Vandenberg’s body forced him into retirement at the end of 2007 – just 12 months before Hawthorn’s famous upset of Geelong.

“There was a group of us, Joel Smith finished up at the same time, Ben Dixon finished up at the same time, we’d all been there for 10 years or more. We finished up at the end of 2007 season,” Vandenberg says.

“We’ve spoken about it, it was very bittersweet. It was fantastic that the guys won, we were still very close friends with a lot of them, but of course there’s that little bit of self-reflection of wishing you were there but the reality is, had we been there, it may not have happened.”

Fraser too still feels the disappointment of not winning football’s ultimate prize, playing in losing a grand finals in 2002 and 2003 with Collingwood.

“I probably feel a little bit unfulfilled in some ways,” he says.

“Probably a lot of players who don’t play a lot of footy and they’ve been able to play in premierships, they probably feel pretty satisfied, guys that might have only been in the system for five or six years.

“So to be in the system for 13 years and missed out, probably leaves a bit of a hole in my stomach to be honest.”

If I knew then …

But even with a premiership, Headland still gets a little wistful when he discusses his footy career, and he is direct when discussing the advice he would give to all the hopefuls on the Gold Coast.

“I’d tell them just to take it with both hands because you might never get this opportunity again,” he says. “I’d definitely do it again in a heartbeat if I could, but that can’t happen.”

Vandenberg’s advice is even more succinct.

“If you love it, just do the best you can. I just loved playing footy.”