His AFL debut in 1999 left him feeling embarrassed after being flattened by North Melbourne hard man Glenn Archer in front of his mates at the SCG.
But his last game in August could place Lenny Hayes on the same pedestal as his idol Robert Harvey, as a four-time St Kilda club champion.
Hayes admitted to choking back tears on Tuesday when he told his teammates he would be retiring at the end of the 2014 season.
The 34-year-old midfielder will be stranded three shy of the 300-game milestone if he plays all six remaining matches for the last-placed Saints.
St Kilda skipper Nick Riewoldt says Hayes' form is so good that he's probably the club's leading player at the moment.
Judging by the way his teammates donned "I love Lenny" t-shirts on Tuesday, the departure of Hayes will also be keenly felt.
"I think I cried more when Robert Harvey retired (in 2008) than I did telling the boys that I was finishing up," Hayes said.
"That was probably just a sign that I was really comfortable with the decision.
"I felt like I'd given it everything that I had.
"I've always liked to set the example both on the training track and on the field. I just feel I'm probably on the edge of the cliff in terms of my body.
"In terms of the decision, as a player it's always really hard to say those words."
Hayes is St Kilda's only Norm Smith Medallist, claiming the honour in the drawn grand final against Collingwood in 2010.
He doesn't spend any time thinking about how the bounce of the ball went against the Saints in 2010.
"For a long period of time, I'm really proud of what we stood for as a football club," the three-time club champion said.
"To play in some big games in front of big crowds and get the job done, there's no better feeling in football.
"Unfortunately we didn't get the ultimate prize. But I feel comfortable in knowing that we gave it absolutely everything we had.
"I don't have any regrets and I don't think as a team we should either.
"Sometimes in football and in life it doesn't go your way."
St Kilda coach Alan Richardson says Hayes has been a great mentor to his younger teammates and Hayes says he's interested in a coaching career.
Hayes had asked the club to keep his media conference "low-key", without success.
"I've had some pretty serious injuries and I feel like the club has always really supported me through those," Hayes said.
"I did my knee when I was over 30 and had the open-heart surgery as well (in 2012).
"The club never mentioned retiring to me."
Hayes says the tag of most-admired player in the competition doesn't sit comfortably with him.
"Over my career I've tried to treat people the way I'd like to be treated, and that's respectfully," he said.
"If people warm to me through that then that's nice. As a player I've always just wanted to be respected by my teammates and by the club and I feel like I've got that."
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