Ever the enigma, Mr Chen Show Mao has kept his reasons for mounting a leadership challenge close to his chest.
When asked by reporters a day after his failed bid why he had stood for the post of secretary-general, he first gave a non-specific reply: "It gave us an opportunity to exercise our democratic rights."
But, in words hinting at possible discontent among some quarters in the Workers' Party (WP), he added that the Central Executive Council (CEC) election gave members a chance to "choose how to govern ourselves for the next two years".
Mr Chen's thinking when he decided to accept the nomination for secretary-general may also have been foreshadowed much earlier - in his maiden parliamentary speech in 2011.
He noted then that Singaporeans told him there were political fault lines here, and that such divisions were not conducive to unity and the country's development.
Speaking in Mandarin, he asked: "But how are these divisions caused? Is it because different voices have emerged in society or is it because we cannot accommodate different voices?"
Party insiders say Mr Chen could have been contemplating a challenge in 2014, when the WP last held its CEC election.
But he, or his backers, decided to hold off after doing the maths and realising there would not be enough votes to prevail, they add.
The May 29 election, on the other hand, was a favourable time for a challenge for three reasons, say these well-placed WP members.
First, a win by Mr Chen now would give him a clean slate to build his record for the next general election. It would not have been the case if he had done so and won in 2014. With a GE then looming, Mr Chen would have had to lead the WP while hoping that Mr Low's past stewardship would still rub off on voters - an awkward position for a new party chief to be in.
Second, a challenge in 2014 - near the end of an electoral cycle - would have given rise to public and voter concerns about the WP's internal stability. Had he mounted a challenge it might also not have translated into the kind of results the WP achieved nationally in GE2015. Even if he had won the post, he would have had little time to consolidate his position ahead of the national polls.
Lastly, the WP believed it was on a trajectory where voters were willing to vote for the opposition. And if the WP was confident of retaining and building on its gain of Aljunied GRC, a failed leadership challenge in 2014 could have translated into Mr Chen being dropped from the WP slate in GE2015.
But by mounting a challenge now, Mr Chen has a good gauge of his level of support among WP cadres. And should he decide to do so again in 2018, it will not come as a shock to members.
The question for Mr Chen, say observers, is this: What's next?
Party members tacitly acknowledge that his performance in Parliament has been lacklustre. Support within the party may also have weakened. Both members who put him up for party chief - Mr John Yam and Mr L. Somasundaram - lost their re-election bids. Yet fresh faces aligned to Mr Low Thia Khiang were elevated to the CEC.
In a fresh response yesterday to The Sunday Times on his decision to contest, and to what members said about his performance, Mr Chen would only say: "I considered whether to contest and finally decided to accept the nomination as I believe the party ought to stand tall enough to undergo this open democratic process, and that WP leadership will emerge the stronger for it. Now that the elections are over, much remains to be done and we in the WP stand behind the elected CEC under Thia Khiang's leadership."
Analysts believe that while he and Mr Low has struck conciliatory tones, Mr Chen's challenge has lasting consequences.
Given that he garnered 42 per cent of the vote in a party known to value internal discipline, National University of Singapore political scientist Bilveer Singh says the WP is now likely to close ranks and work towards having a more predictable CEC election come 2018.
"This will probably be the last time you see this type of 'democracy' as WP leaders will solidify the party so that the public will not doubt it as a united party of the future," he says.