A strong crop of nominees made the process of deciding the winner a difficult one for the award's 15-member judging panel, which included editors and senior writers from The Straits Times and others from various walks of life.
The number of finalists also grew from 10 last year to 12 this time, noted youth leader David Hoe, 29, one of the judges. "Every one of them had traits that Singaporeans could aspire towards... Because of this, we had many rounds of deliberation," he said.
Some, like security officer Peter Lim Kok Seng, 55, who donated part of his liver to a stranger, embodied selflessness, noted Mr Hoe.
Others, like Wong Fong Industries' Mr Eric Lew, 43, who injected new life into a family-run company by setting up a research and innovation centre, demonstrated how Singaporeans can ride the technology wave and be receptive to changes disrupting the economy.
But the Schoolings' remarkable story, of their tenacity and determination, year after year, to chase and attain the greatest heights of sport, won the panel over.
"In this time and age of uncertainty, the Schoolings' story was one of how everyone - the older generation with the experience, and the young with dreams - can come together to move forward," said Mr Hoe.
ST executive editor Sumiko Tan said: "When Singaporeans look back at 2016, who can forget that moment Schooling beat Michael Phelps - Michael Phelps! - to win Singapore's first Olympic gold medal? His win really brought Singaporeans together."
Social entrepreneur Saleemah Ismail, 48, hopes the tribute to the Schoolings will spur "more parents to take a leap of faith, and trust that their children can take that non-conformist path". "The sacrifices and acts of courage made by parents should be applauded."
Said ST editor Warren Fernandez, who is also editor-in-chief of Singapore Press Holdings' English, Malay and Tamil Media Group: "We had to pick one winner, but the 12 finalists were all winners, whose stories of compassion, perseverance, initiative, and true grit deserved to be celebrated."