Having been named best-on-ground for Noble Park in the 2004 Eastern Football League Grand Final, Gwilt also relinquished a promising Premier Cricket career with South Melbourne before joining the Saints.
He then went from a 'smoky' to a surprise selection when he made his AFL debut on the eve of the 2006 finals, playing his first match against the Brisbane Lions at Telstra Dome in round 22.
Gwilt then played in St Kilda's qualifying final win against Adelaide and its loss to Sydney in the preliminary final, capping off a remarkable rise in less than 12 months.
Fast forward to 2008 and Gwilt's career, as he says, has had its "ups and downs", with a serious ankle injury, considerable time at VFL level and 19 matches coming since.
"'[It's been] frustrating at times," Gwilt told saints.com.au.
"In my second year, I hurt my ankle and missed seven or eight weeks and it took its toll a little bit and I hadn't missed that long before and I'd never been injured before, so it was a bit of shock to miss eight weeks of footy.
"You lose your touch and fitness, so 2006 was a bad year, but I was lucky enough to get another two-year contract when Rossy came to the club and he's improved my football.
"I think the club's happy with my progress, but I've still got a long way to go … I think I'm improving week-by-week, which is what I want to be doing."
Still, Gwilt may be on the verge on seeing more 'ups', with the versatile Saint has playing six of the past eight matches for St Kilda. His performance against Port Adelaide at Telstra Dome on Sunday was particularly encouraging.
"I was concentrating on my effort and intensity and it was there for the whole game," Gwilt said of his round 18 match.
"[Ross Lyon] was pretty pleased with the whole team's effort.
"It's been enjoyable and it's good to be winning and it's good to be back, after concentrating on a few things that the coaches and the teammates have been wanting me to work on … I've been working on them at training and hopefully they're starting to pay off in games."
The almost 22-year-old (his birthday is on August 11) said his hard work was now translating into self-belief at the elite level.
"The first half of the season I was playing with the Casey Scorpions and I wasn't playing too bad", Gwilt said.
"But it was a matter of taking the next step and trying to take my footy a bit further. My fitness has definitely improved and that gets your confidence up a bit, because you know you can run a game out playing forward or back or running with blokes.
"I enjoyed going forward last week for the first time in a while, because I used to play forward a couple of years ago. But I don't mind where I play, as long as I'm playing."
