With a pledge of free bananas for the town's children, football mascot H'angus the Monkey was the "joke" candidate to be mayor of Hartlepool.
Some 11 years later - and with three election victories under his belt - it seems Stuart Drummond, who leaves office on 5 May, was no comedy character.
A referendum in November signalled the end for the mayoral system and Hartlepool Council will instead be governed by committees.
Tapping away at his keyboard with framed Hartlepool United shirts and squad photographs behind him, Mr Drummond joked he had seen "too much" of his beloved team's relegation season.
He still has a season ticket at Victoria Park where his campaign began as a stunt.
"I was always looking for something new to get a little bit of publicity for the club and just have a bit of fun along the way," he said.
The club's chairman loaned his mischievous mascot the £500 deposit and things soon got serious.
"Never for one second did I expect to win," he said. "I hadn't prepared for anything, it was a case of winging it and making it up as I went along."
Mr Drummond, a father-of-three, said he had an "extended honeymoon period" with those outside the civic centre, but not some of the councillors he was working alongside.
"The public saw me as one of them and almost put a protective arm around me to support me through those early years.
"Getting the respect and credibility from councillors? I probably haven't even got it from some of them now, but that was always going to be a challenge."
There was a "huge shift" in attitudes, Mr Drummond said, when he was re-elected in 2005 with a majority of more than 10,000.
He looks back over his tenure with pride.
"I've been quite overwhelmed by the support I've been given from people and the amount of people who have expressed their disappointment at what's happened," he said.
"If all those people had voted in the referendum we might have had a different result."
The mayor insisted the result of the poll does not rankle with him personally as he would not have stood for a fourth term.
"It's a shame that nobody else will get the opportunity to step into my shoes and bring a fresh pair of eyes to it and take it to the next stage," he said.
"It's not really the system of governance that's important, it's about how the town fares and the decisions that are made."
Having one directly-accountable figurehead for the town has helped Hartlepool punch above its weight, Mr Drummond believes.
"Hartlepool is like one of the biggest villages in the country. There's a strong community spirit and a lot of local pride here.
"To have somebody to be able to promote that on a regional, national and international basis is a big benefit."
Hosting the Tall Ships in 2010 gave the town a huge boost in confidence, the mayor said.
"For us to bring the world to Hartlepool and see so many people smiling and enjoying themselves, that doesn't really happen that often.
"Every day in this role you're always trying to improve things and make people feel better in their own lives. The Tall Ships did it perfectly."
Mr Drummond took a deep breath before describing the "most challenging" role of his life.
Soon after joining Cleveland Police Authority, he found himself elevated to chair.
"Little did I realise the 12 months that lay ahead," he said.
"I didn't realise the state the authority was in. It was on the verge of government intervention because it was so poorly governed."
Operation Sacristy, a criminal investigation into allegations of corruption at the authority, began in May 2011, six months before Mr Drummond took over.
The investigation continues and the former chief constable and deputy chief constable have been sacked for gross misconduct in recent months following separate misconduct hearings.
"If it was a TV drama it would be quite hard to believe," Mr Drummond said.
"In the fullness of time everything will be made available and people will make their own conclusions. All I can say is I wouldn't want to go through that again."
If Mr Drummond breathed a sigh of relief on leaving his police role, his wife Rebecca will be even happier when he leaves his current job.
"She cannot wait for 6 May when I won't be elected mayor anymore. She doesn't like the attention it brings and some of the publicity. She's really looking forward to it."
So what does the future hold? There are, Mr Drummond said, "a couple of irons in the fire".
"I've had some interviews recently and I've been telling some of these tales and people have been flabbergasted.
"From day one the whole thing has been unconventional. It's not a bad thing to have on your CV I don't suppose.
"Whatever I do next I will always be banging the drum for Hartlepool.
"That's in my blood now."