SINGAPORE — For a hot minute on Nomination Day, WP chief Pritam Singh hopped on a bus bound for Yusof Ishak Secondary School – the nomination centre for East Coast and Punggol GRCs – teasing what looked like a bold departure from the party’s Aljunied stronghold to conquer new ground.

But the Leader of the Opposition would then alight, and subsequently board another bus bound for Poi Ching School, the nomination centre for Aljunied GRC, where he would eventually contest.

If he had left with the first bus, things might have panned out differently at the polls on May 3, with the WP potentially winning more seats instead of retaining its existing 10.

“In hindsight, everybody is a master,” Mr Singh himself said on May 4 when asked how he would have conducted things differently.

Political observers said the way the WP played its cards this general election was ambitious and conservative in equal parts – a paradoxical mix of bold manoeuvres and calculated restraint that ultimately delivered mixed results, offering both reason to celebrate and cause for regret.

Conservative, because the party’s top brass – Mr Singh and chairwoman Sylvia Lim – stayed put in their Aljunied “home base” along with head of policy research Gerald Giam, choosing only to swing vice-chair Faisal Manap out to Tampines GRC.

Ambitious, as the WP appeared to have deployed its candidates in a way that gave it the best possible chance to win big – all 26 of the 97 seats it was contesting, which would have been a leap towards its medium-term goal of securing a third of Parliament from the 10 seats it held.

Several aspects of its campaign hinted at this game plan to chip away at the PAP’s vote share uniformly across all eight battlegrounds where the 26 were fielded.

One, the WP spread the deployment of its higher-profile first-time candidates – such as Senior Counsel Harpreet Singh, former Institute of Mental Health director Ong Lue Ping, and start-up co-founder Michael Thng – across Tampines and Punggol GRCs, not prioritising either one.

NTU political scientist Walid Jumblatt Abdullah opined that had t...