In the last 14 years, the Workers' Party (WP) has tried three times to win over East Coast residents to its cause. But despite getting closer in 2011, when the national mood swung against the ruling People's Action Party (PAP), voters remained ultimately unconvinced.
This year, the WP is mounting a fresh challenge. But much has changed in both camps since the last time Singaporeans went to the polls.
For the PAP team, this year's general election marks the end of an era. Mr Lim Swee Say, the constituency's anchor minister, is likely to retire. But the identity of his successor is perhaps the party's best-kept secret so far.
Their long-time opponents in East Coast are also playing their cards close to their chests. Although it is clear that the WP's 2015 team will not return for a second bout, the party has given no indication of what its new line-up will look like.
Lastly, the single seat of Fengshan, carved out of East Coast in the last general election, is now returning to the fold.
The ebb and flow of political tides in East Coast over the past three elections has made it a constituency to watch, as both sides start squaring off to secure the mandate of its 121,772 voters.
But with much about each party's slate still undisclosed, it remains unclear what shape this battle will take.
GUESSING GAME
All signs indicate that East Coast is likely to lose its anchor minister, Mr Lim, who has seen the constituency through two general elections and notched up a total of 23 years in politics. Mr Lim himself was moved to the constituency a month before the hustings in 2011 to shore up the PAP slate then.
No official announcement has yet been made. But Mr Lim had previously indicated on two separate occasions that the 2011 election would be his last, making his retirement, in a sense, overdue.
Activists expect his successor to come from a group representation constituency with two anchor ministers. At one point, the talk centred on Minister for Social and Family Development Desmond Lee, who is currently an MP for Jurong GRC. The constituency is helmed by Senior Minister Tharman Shanmugaratnam.
But recent developments have made this possibility seem increasingly unlikely. Mr Lee has been making virtual appearances at West Coast GRC events in recent weeks, prompting speculation that he could move there to bolster the PAP team.
Another four GRCs - Bishan-Toa Payoh, Pasir Ris-Punggol, Tampines and Tanjong Pagar - have ministers to spare.
But the majority appear to have already been earmarked for posts in other constituencies, leaving just four options for East Coast.
Tanjong Pagar GRC could offer up either Trade and Industry Minister Chan Chun Sing, or Minister in the Prime Minister's Office Indranee Rajah.
And Tampines - which shares a boundary with East Coast - has Deputy Prime Minister Heng Swee Keat and Minister for the Environment and Water Resources Masagos Zulkifli.
Dr Gillian Koh, who is deputy director for research at the Institute of Policy Studies, says the opposition will not be in for an easy fight if a fourth-generation PAP leader is fielded in East Coast.
This will also be the case if a strong 3G leader is fielded, she adds.
Aside from Mr Lim, East Coast will also lose three-term MP Lee Yi Shyan, who was Senior Minister of State for Trade and Industry and National Development until he returned to the backbench in 2015, following a minor stroke.
Mr Tan Kiat How, the 43-year-old former chief executive of the Info-communications Media Development Authority, is tipped to succeed him.
The constituency's two other MPs - Senior Minister of State for Defence and Foreign Affairs Maliki Osman, and three-term backbencher Jessica Tan - are likely to stay on. Joining them will be one-term Fengshan MP Cheryl Chan, whose single-seat constituency is now part of the GRC.
HOT SEATS
In 1997, Bedok GRC was expanded to take in parts of Eunos, Marine Parade, Tampines, Changi and Aljunied. This amalgamation was renamed East Coast GRC. The new GRC went uncontested in that year's election, as well as the next, in 2001.
It saw its first electoral battle in 2006, when a WP team led by lawyer Chia Ti Lik - then deputy organising secretary of the party - entered the fray. The PAP team, helmed by then Deputy Prime Minister S. Jayakumar, sent their opponents packing. The WP's vote share then was 36.1 per cent.
In 2011 - the year in which the PAP's overall vote share fell from 66.6 per cent to 60.1 per cent - the WP mounted a fresh challenge. This time, it was up against a team led by then labour chief, Mr Lim. The PAP team won with 54.8 per cent of the vote. East Coast was the worst-performing GRC won by the party that year.
The next general election in 2015 saw a massive national swing towards the incumbent, which secured 69.9 per cent of the popular vote. In East Coast, the men in blue nevertheless garnered a 39.3 per cent vote share.
Its slate comprised IT consultant Gerald Giam, former librarian Mohamed Fairoz Shariff, sociologist Daniel Goh and consultancy firm chief executive Leon Perera. The last two were subsequently appointed Non-Constituency MPs (NCMPs) - seats reserved for losing opposition candidates with the highest vote shares.
That year, Fengshan SMC was also carved out of East Coast and subsequently became the subject of a heated electoral contest between long-time PAP grassroots volunteer Cheryl Chan and the WP's Dennis Tan, a shipping lawyer. Ms Chan won with 57.5 per cent of the vote.
The WP's 2015 slate will not be making a comeback this year. Associate Professor Goh has dropped out of the running, citing health reasons, while Mr Giam and Mr Perera will move to contest as part of the WP's Aljunied GRC team instead.
Who, then, will the WP send to East Coast? The party has traditionally sent its B Team to contest the constituency. But the creation of a new Sengkang GRC, coupled with Emeritus Senior Minister Goh Chok Tong's decision to step down as an MP in Marine Parade GRC, could give it pause for thought.
"East Coast appears to have moved down the WP's pecking order," notes Singapore Management University law don Eugene Tan, a former Nominated MP.
"They have long contested in East Coast GRC, which has yielded them a few NCMP seats, and seek to keep faith with the voters who previously voted for them. But it seems like the WP's second-best GRC line-up will be in Sengkang."
THE COVID-19 FACTOR
East Coast residents whom Insight spoke to say they are generally happy with the ruling party's performance in their neighbourhoods. Even so, many desire more opposition voices in Parliament and the Covid-19 pandemic weighs heavy on their minds.
Ms Siti Khadijah, a 30-year-old teacher, says many upgrading works have been carried out in her neighbourhood over the years. But she has never had an MP visit her home.
"I would love to see my future MP getting to know residents and doing more house visits to connect with us," she says.
"I would not mind giving the opposition a chance this year because I want to see what they have to offer and what they can do for the people," she adds.
Mr Kwan Fook Choy, 67, says: "To me, it's important that a candidate is of good character and has a heart for the people. But I also believe it's important to have some opposition in Parliament to balance out the PAP."
For other voters, the Government's handling of the pandemic and its decision to call an election now will play into their decision at the ballot box.
Mr Hashim Ali is one of those who feels that the election has been called too soon, and is unconvinced by the ruling party's explanation for why it has done so.
"Things are not stable yet. I'm not against the Government; they have done a good job," says the 57-year-old, who works part time as a security guard. "But the big question is: 'Why now?' If they can give me a good explanation, I will vote for them."
Others, like a 40-year-old who wanted to be known only as Aida, are more swayed by the ruling party's response to the pandemic crisis. "The PAP has done a good job during the Covid-19 crisis and handled it well. That's important to me."
• Additional reporting by Jolene Ang
