Marcus Gayle was a Crazy Gang member and one of the Reggae Boyz.
Now, as manager of the Staines Massive, he is looking to lead Staines Town into the second round of the FA Cup for only the third time in their history.
The 43-year-old former Wimbledon and Jamaica forward is going back to "the club where it all started" when he takes the Swans, who are mid-table in Conference South, to Brentford in the first round on Saturday.
Gayle began his career as an apprentice with the Bees in 1988 and went on to make 229 appearances in two spells at Griffin Park.
"It shaped my career and my character as well, in terms of how to appreciate the game," Gayle told BBC London 94.9.
"I learnt some tough lessons but some valuable life skills at the same time. I've got fond memories of the whole ground.
"I spent two solid years cleaning out the changing rooms every day. I cleaned boots, the stands and did odd jobs.
"It was basically a nine-to-five job for not very much money but at the end of it we all knew we had an opportunity to train and play with the first team and have a chance of forging a career at the club.
"The life skills we learnt, and the appreciation of what we do in football, was ignited at Brentford. I fully appreciate the opportunity I was given as a 16-year-old school leaver to ply my trade with a well-run club.
"It means a hell of a lot to me to go back there and I want to reflect that back towards the club and the fans."
Hammersmith-born Gayle left Brentford in March 1994, joining Wimbledon for a fee of £250,000. He spent seven years with the Crazy Gang and during that time played for Jamaica at the 1998 World Cup.
His 20-year playing career, which also saw spells at Rangers, Watford and Aldershot, included a second spell at Brentford in 2005-06 - when the Bees missed out on promotion to the Championship via the play-offs.
Gayle's playing days ended at AFC Wimbledon in 2008, when he became the Dons' reserve team manager, and he took the Staines job in May 2012.
"I left a League Two club in AFC Wimbledon to further myself and my career," he said.
"I took a chance in dropping down but in my eyes it was a chance to step forward into management. The chairman Matthew Boon took a bold step in bringing me in.
"Staines have given me the opportunity and believe in what I am doing. I have got a stage to perform on now.
"We wanted to give the club a fresh outlook, raise the bar and the standards.
"Hopefully I have done that with my professional background and, with all the experience I have had, try to implement those qualities into a non-league side and make this club appear as professional as possible."
Gayle describes himself as a "deep-thinking manager" despite his laid-back appearance.
"I am extremely passionate, just as I was as a player," he said.
"I wasn't loud but I was an impact player. I was a man of action and as a manager I still have those qualities - I have just got to divert them into communication skills."
After entering the competition in the second qualifying round, Staines have beaten Aylesbury United, Sittingbourne and Poole Town to reach the first round proper.
On their previous two appearances in the second round, the Wheatsheaf Park outfit lost to Peterborough in 2007-08, and were knocked out by Millwall in 2009-10, losing 4-0 in a replay at the Den after a 1-1 draw in the original tie.
Standing in their way this season is a Brentford side that reached the fourth round last season, losing to Chelsea after a replay.
The Bees, managed by Uwe Rosler, have won their past four games in League One.
"In pre-season we wanted to be in the first round," Gayle added.
"We have got there and now it is a chance to perform and play with pride. If Brentford do take it a bit lightly we are their potential banana skin.
"We are here on merit and have progressed nicely in 18 months. It is a deserved game for the players and just rewards for the chairman.
"We believe we have got a genuine chance but nerves will play a part on the day. It will be a special occasion, not just for myself but also the whole club."
Interview with Marcus Gayle by BBC London 94.9's Jamie Reid.