Two years ago, some long-time Workers' Party (WP) cadres backed Mr Chen Show Mao's challenge against long-time party chief Low Thia Khiang for the role of WP secretary-general. They were unhappy at how Mr Low has been fielding younger and newer party members at general elections.

Since then, some in the party have avoided this group.

Not one man.

WP assistant secretary-general Pritam Singh quietly reached out to the group's leaders last year to better understand their issues and try to smooth things over, said a party member from the group who spoke on condition of anonymity.

"He knew they were unhappy and wanted to speak to them," said the member in his 60s.

The effort to reach out helps to explain how the 41-year-old, within eight short years of joining the WP, became the favoured candidate to succeed Mr Low as chief of Singapore's biggest opposition party.

On paper, Mr Singh did not seem a natural successor to Mr Low, who has left his indelible imprint on the WP that he has helmed for 17 years.

Chinese-educated, Teochew-speaking with a gift for colloquial and hard-hitting speeches, and politically shrewd, Mr Low, 61, led the WP to unprecedented heights - including the wresting of a group representation constituency from the ruling People's Action Party (PAP) in 2011. He has said he wants to step down this year.

Mr Singh, who obtained his law degree with Singapore Management University's Juris Doctor programme, is relatively inexperienced in politics. Yet, interviews with party members, residents and political observers yield the broad strokes of a man who they say is more similar to Mr Low than not: Both are known for their effectiveness in communicating, their down-to-earth manner - and the ability to be direct and blunt when it matters.

Mr Singh declined to be interviewed for this article.

One well-known tale among party members is that when confronted by unreasonable or long-winded residents during sales of the party's Hammer newsletter, Mr Singh is often the one still patiently listening after others have left. "He is friendly to work with and his residents like that," said Mr Gurmit Singh, a grassroots volunteer for Mr Singh.

Eunos resident Aziz Naim, 56, said: "He always says 'hi' first when he sees me. A leader should be sincere and not snobbish."

His party colleagues said Mr Singh is well-liked for his consultative manner and for leading by example. Said former Non-Constituency MP Yee Jenn Jong: "He is very fair. It's more a discussion and he listens to what you have to say."

But in 2010, when a 33-year-old Mr Singh walked up the narrow stairs of the WP's former headquarters in Syed Alwi Road and asked to join the party, it was his bite that impressed party members.

Party cadre Frieda Chan, who knew Mr Singh from their undergraduate days in the 1990s, said he has always been passionate and vocal. In a bid to better understand and discuss religious issues, he had done a diploma in Islamic studies.

The former Jurong Junior College student's argumentative abilities honed in law school would come in handy in Parliament, winning him plaudits among party members.

Even former WP chairman John Gan, who supported Mr Chen in his bid to become party chief, agrees Mr Singh has done well: "Pritam is daring in Parliament and able to voice out on many issues, which is why many are behind him."

In his maiden speech in Parliament, for instance, he pushed for freedom of information legislation, drawing a rebuttal from Law Minister K. Shanmugam.

But Mr Singh also made some missteps when he first entered Parliament in 2011, full of football analogies and often crossing swords with PAP leaders. For instance, he came across as arrogant and overly combative, noted some. On one occasion, during a debate on the WP's town council troubles in 2015, he had refused to answer questions put to him by various MPs, saying his duty was only to Aljunied GRC residents - drawing flak from the public.

Mr Singh has since mellowed, choosing his words with greater care, said those interviewed. WP's deputy organising secretary Kenneth Foo Seck Guan puts this down to Mr Singh's sharper political acumen and presentation skills acquired over the years. "He seems to have learnt how to present a better tone. He is assertive, and not aggressive," he said.

Some say luck had a part to play in Mr Singh's success. He became an MP a year after he joined the party, when the WP team in Aljunied scored victory on the back of voters' unhappiness with the PAP.

Others say he made his own luck. While he is one of those embroiled in the WP's ongoing Aljunied-Hougang Town Council saga and is facing a lawsuit over it, he has since helped resolve the issues there.

In 2015, he took over as chairman of the town council from party chairman Sylvia Lim. Working with consultancy KPMG as town council chairman, he has fixed 15 of the 17 issues flagged in a special audit.

Said Mr Foo: "Everyone, including himself, knows it is no easy task, but he took it on and did it well."

After years of the WP being associated with Mr Low, some wonder if Mr Singh can connect as well to the party's traditional base of Chinese-educated voters and senior cadres. Political scientist Derek da Cunha feels it is not clear if Mr Singh's ethnicity would affect the party, since it has been led by non-Chinese before - Mr David Marshall and Mr J.B. Jeyaretnam - and "so going for another non-Chinese as leader would not be new or novel for the WP".

Whether it will indeed be Mr Singh will be decided on April 8, at the party's leadership elections.

Party leaders from start to present

DAVID MARSHALL

Chairman (1957 to 1963)

The Workers' Party was founded in 1957 by Mr David Marshall, who envisioned it as a moderate alternative to "the left-wing PAP and the right-wing Labour Front".

The lawyer became Singapore's first chief minister when the Labour Front formed the coalition government in 1955.

But he stepped down 14 months later after failing to secure self-government for Singapore, and left the Labour Front.

Riding on union support, he formed the WP, which managed a few wins against the PAP. The first was the 1961 Anson by-election, which Mr Marshall won.

But he left the party in 1963 after being deceived by fellow members, and WP fell dormant.

J.B. JEYARETNAM

Secretary-general (1971 to 2001)

In 1971, Mr J.B. Jeyaretnam led a team of lawyers, unionists, businessmen and educators to take over and rejuvenate WP.

He was elected in the 1981 Anson by-election, becoming the first opposition MP post-independence, and was re-elected from Anson in the 1984 General Election.

Mr Jeyaretnam was known for his fiery speeches in rallies and for being outspoken in Parliament. But he had to vacate his parliamentary seat and was disqualified from elections until 1991, after he was jailed and fined for making a false declaration in WP's accounts.

He also faced several defamation suits in his time as WP chief, some brought by PAP leaders.

He returned to the House in 1997 under the Non-Constituency MP scheme, but lost his seat in 2001 after he was declared bankrupt.

Mr Jeyaretnam left WP in acrimony in 2001, after accusing Mr Low Thia Khiang of not helping him to pay off his debts - a claim Mr Low has denied.

LOW THIA KHIANG

Secretary-general (2001 to now)

Mr Low, who won Hougang in the 1991 and 1997 elections, took the helm of WP after Mr Jeyaretnam's departure.

He has been credited with building up the party, which has attracted younger, more educated members, including current WP chairman Sylvia Lim.

The WP made a breakthrough under his leadership when its team won Aljunied GRC in the 2011 General Election.

But winning the GRC also brought the WP its biggest problem - its town council was unable to submit clean accounts since 2011, eventually resulting in an audit by the Auditor-General's Office.

Last year, an independent panel representing the town council sued Mr Low and Ms Lim, asking them to account for $33 million in payments.

Mr Low announced during the party's anniversary celebrations last year that he will step down to make way for younger leaders.

Tham Yuen-C