In his maiden electoral battle in Joo Chiat in 2011, Workers' Party's (WP) Yee Jenn Jong fell short by just 388 votes of ousting veteran People's Action Party (PAP) backbencher Charles Chong from the single-seat ward.
Today, the 50-year-old is undertaking a bigger test, leading a five-member WP team to challenge not one but five PAP candidates in Marine Parade GRC.
Doing battle over the next nine days alongside Mr Yee are lawyer Terence Tan, chocolate factory owner Firuz Khan, corporate lawyer He Ting Ru and wealth manager Dylan Ng.
They will clash with the PAP team, made up of anchor minister Tan Chuan-Jin - touted as a fourth-generation leader for the ruling party - elder statesman Emeritus Senior Minister Goh Chok Tong, seasoned backbenchers Seah Kian Peng and Fatimah Lateef, as well as Mr Edwin Tong.
Following the electoral boundaries review last month, the constituency has given up the MacPherson ward and absorbed Joo Chiat.
Up for grabs are the votes of more than 146,000 people, nearly seven times that of Mr Yee's solo battle for the old Joo Chiat.
Can Mr Yee, who had to settle for becoming a one-term Non-Constituency MP in 2011 as one of the best-performing losing candidates, actually wrangle Marine Parade from the PAP team? That is the constituency ESM Goh has represented since 1976 and where he enjoys great popularity.
Three factors should come into play.
First, how convinced will residents be that the WP can run another town council, given the problems that still beset the Aljunied- Hougang-Punggol East Town Council with its finances?
Well aware of the question mark that hangs over his party, Mr Yee said after the close of nominations at Kong Hwa School yesterday: "I think I (will) let the voters decide about the team itself. But what I can confidently say is that these people have actually worked with me on the ground for many years." He said they had "genuine heart" and the know-how to run a town council from scratch.
Second, Mr Yee will have to contend with the gigantic presence of ESM Goh.
The 74-year-old former prime minister, who is fighting his 10th election in Marine Parade, is said to have wanted to retire. But he was asked to stay for at least one more term to help with the transition of the national leadership. ESM Goh said yesterday: "I've served you with sincerity, humility and integrity for some 40 years. My hair has turned white.
"But it's worth it. I stand ready to serve you again."
Still, it is unclear if his presence will shift the tide to the PAP, which retained Marine Parade with one of the party's slimmest margins in the 2011 General Election. It polled 56.6 per cent of the votes - a shocking result against a relatively unknown National Solidarity Party (NSP) team.
This time around, the WP is turning up the temperature of the competition. Its team members have been spotted pounding the pavement and distributing fliers in the last two months. A shopowner in Marine Parade, who declined to be named, added: "They look very sincere and seem to want to listen to what we have to say."
Third, the WP new faces say they have the "home advantage". Among the five candidates, three - Messrs Yee, Tan and Firuz - live in the GRC and are familiar with the estate and residents.
Some PAP activists concede it will be an uphill battle to improve on the winning margins, despite the feel-good factor from the SG50 celebrations.
But when asked about the tougher fight, ESM Goh seemed unfazed, noting that opposition parties come and go. "In Marine Parade's case, since the 1990s, there were three or four parties which have come and gone. Now a new tribe is coming. Do they really have interest in Marine Parade's people's welfare?
"I've spent 40 years there. I built up a community," he said, adding he would leave it to voters to decide whether he had done a good job.
Still, the PAP team is going all out to reach the hearts, minds - and eventually votes - of constituents by going door to door.
Mr Tong, who was deployed to the Joo Chiat ward after the Moulmein-Kallang GRC was wiped from the electoral map, has been walking the ground. He has also been getting support from ESM Goh and Mr Tan Chuan-Jin.
As Mr Tan said yesterday: "Whatever that needs to be done, we have been doing it over the last four years... Whether general election or no general election, our duties remain, our focus remains very clear. It's always about our people."
This article was first published on September 2, 2015.
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