When Workers' Party (WP) chief Low Thia Khiang was first elected secretary-general in 2001, he was the youngest member of the Central Executive Council (CEC).
Two weeks ago, after seeing off his very first challenge for the same post, he observed with satisfaction that he was now the oldest.
The circumstances in which he took over the WP explain his emphasis on party renewal and the need to bring in fresh blood to its leadership ranks.
In 2001, Mr Low was taking over the reins of a WP that had enjoyed electoral success in having won the Anson by-election in 1981, and having earned two Non-Constituency MP seats over the years.
But the party was also stagnating, failing to attract enough promising new leaders, while its previous secretary-general J.B. Jeyaretnam, was mired in expensive libel action.
Over the next 15 years, Mr Low shaped the WP into Singapore's leading opposition party by paying attention to the finest details - even playing fashion police by making party activists don more formal attire at outreach activities to give them a more respectable and serious image.
However, the spectre of a political party filled with ageing members continued to haunt Mr Low, and two weeks ago, he described how it was a "very scary" prospect for a party to be without clear succession plans.
It appears that he is ready to enter the next phase of party renewal, having described the current CEC as being the best team he has assembled so far.
Beyond the WP's rejuvenation, Mr Low also played a crucial role in breaking the People's Action Party's (PAP) monopoly on GRCs.
This crowning achievement came in the 2011 General Election, when he left the safety of his Hougang single-member constituency to contest and win Aljunied GRC.
Political observer Derek da Cunha feels that the party's electoral success under Mr Low is enough for him to secure and cement his place in Singapore's political history.
"Ultimately, the only standard - and it is a standard applied around the world - by which one should judge the leader of a political party is the number of seats his party secures in the legislature. Everything else is secondary," he says.
He goes on to point out that Mr Low's predecessor, Mr Jeyaretnam, could secure only one elected seat for the WP in Parliament at any one time during his 30 years as party chief.
"On the other hand, Mr Low secured six fully elected MPs in GE2011, which was a decade after he took over the helm of the WP," he adds.
"If a party leader consistently fails to secure parliamentary seats for his party, then the convention around the world is that such a person should step down as leader. Clearly, this is not an issue that applies to Mr Low.
"The WP has nine parliamentarians - six MPs and three Non-Constituency MPs. It does not share the parliamentary limelight with any other non-PAP party."
Seen in this light, the leadership challenge by fellow Aljunied GRC MP Chen Show Mao may warrant just a footnote in Mr Low's long and storied political career.
But the contest could still cast a pall on Mr Low's legacy should it lead to disunity within the Aljunied team and ultimately cause them, and the party, to lose at the polls.
In the meantime, Mr Low has moved to close ranks publicly and has refused to be drawn into commenting on Mr Chen's leadership challenge. Mr Chen has also retained his position as party treasurer, a move which National University of Singapore political scientist Bilveer Singh says makes Mr Low look good and accommodating.
"I do see a purge and marginalisation of those opposed to Low taking place, even though this is going to be a 'slow burn' to show Low's magnanimity and not vengeance," he adds.
Chong Zi Liang