When Mr Goh Chok Tong was deciding who should be deputy prime minister when he succeeded Mr Lee Kuan Yew in 1990, Mr Ong Teng Cheong was his first choice.
But when he put the name to his boss, Mr Lee wasn't impressed.
"His reaction was not very good. He asked why Ong Teng Cheong. He did not say, why not Lee Hsien Loong. But from the way he asked, I could sense it, that he was thinking of the future and the future lay with Lee Hsien Loong, not Ong...
"His thinking was that Hsien Loong had the potential to be the prime minister. If something happened to me and Teng Cheong would take over, future political succession would be disrupted."
As I listened to Mr Goh recount this in one of the interviews for the book Tall Order: The Goh Chok Tong Story, on which I sat in together with author Peh Shing Huei, the thought crossed my mind: Was Mr Goh that naive or was his faith in the elder Lee so absolute?
Mr Goh's answer to a different but related question was revealing: "People think I have been naive and used by him; that I was his stooge and I did not even know I was his stooge. People would come to that conclusion that I was stupid. I was indeed flexible, but I was not a stooge...
"Ours was a close interaction, the regular lunches, and he spoke frankly. In a sense, he moulded me and because I knew him and his purpose, I trusted him, and he learnt not to force me to be someone I'm not."
You might still think him naive, but he stayed on as prime minister for 14 years, overseeing a period which saw Singapore continue its dramatic transformation into a global city of international repute.
Mr Goh's achievements as the man who succeeded Mr Lee to keep Singapore going are well known. But not the inner workings of the men at the top and how they came to terms with each other dealing with affairs of state.
Tall Order contains many such accounts of these interactions, about how an unlikely civil servant rose to become prime minister under Mr Lee's watchful eye, with the son waiting in the wings.
There is also that famous put-down by Mr Lee in front of a live television audience at the 1988 National Day Rally when he revealed that Mr Goh wasn't his first choice because he wasn't decisive enough.
Mr Lee followed it up a week later with even more damaging comments that the man had a problem speaking in public and should see a psychiatrist.
Mr Goh opened up about being humiliated so publicly in the book.
"I was bewildered and trying to figure out why he was doing that for," he said.
As he recounted, he wasn't sure whether it was because Mr Lee wanted to make clear at the outset that he wasn't to blame if his successor did not work out or that he was trying to get the team to reconsider its choice and go for Dr Tony Tan instead.
You can choose to go by Mr Goh's interpretation or form your own Machiavellian version.
It is what makes Tall Order such a fascinating story. Even when you have the man at the top telling it, you can't be sure it is the complete story.
Whatever the truth, it could not have been easy for Mr Goh following on the heels of the giant Lee because he was in many ways exactly what Mr Lee wasn't - an awkward, unnatural politician without the killer instincts to destroy his political opponents.
But he and his colleagues learnt quickly under the tutelage of bosses who gave them space to grow in their jobs.
One early example: Mr Goh prepared the Government's Budget in only his third year as a senior minister of state in the Ministry of Trade and Industry.
"If you look back in history, I am the first non-finance minister to present three Budgets. The first was in 1979. Mr Hon (Sui Sen) had sent the whole file to LKY with a scribbled note: 'This is the Budget prepared by SMS.' He had not made a single correction. It came back approved. Lee Kuan Yew (LKY) made about two, three small editorial corrections - that was all."
That same year, he and Mr Lim Chee Onn, both political novices, were asked to take charge of by-elections called by the People's Action Party (PAP) in seven wards.
They repaid the confidence their senior charges had in them by delivering results and by their faith to the cause, shaped principally by Mr Lee.
Mr Goh was probably the most trusting of the lot. He trusted Mr Lee almost absolutely, even when, at times, he must have felt hard done by. It could not have worked otherwise.
The way they were chosen and inducted into politics would form the template for future political succession in Singapore.
But the question remains if the model still works.
The issue is especially relevant today as the country awaits the choice of the next prime minister and the transition to the fourth-generation (4G) leadership.
Mr Goh's accounts raise several important issues about how political renewal in Singapore works and the implications for the future.
The first concerns the nature of the cohort which Mr Goh belonged to, technocrats with no prior experience or interest in politics but persuaded by Mr Lee to join the party because there was a job to be done.
As one member of that team, Mr S. Dhanabalan, put it, while most people elsewhere entered politics for personal ambition or a strong conviction that the government of the day was on the wrong track, it was not the case for him and his peers.
"We never said we wanted to be leaders because of the high standing in society or we wanted to change the system, that this or that policy was wrong and we had to change it," he said.
"We all came in because we agreed... that successful people, in business or civil service, if they did not come forward to enter politics, then the wrong people would come in... and that would be disastrous for Singapore."
There was no jostling for the top job. If anything, no one wanted it, and, as a result, they supported whoever was chosen.
It is important to understand how this attitude developed in the group, among men of different backgrounds but shaped by the circumstances of the time.
They were pioneers making the transition into political leadership, prepared to face an uncertain future with no promise of monetary rewards. (It was only later that ministerial salaries were pegged to private-sector rates.)
Much has been made of the PAP's selection system which is now a hallmark of the party, but Tall Order has a more important message: Leaders are shaped more critically by each generation's unique circumstances and values, which, in turn, affect how they work as a team.
Whether subsequent cohorts succeed as well with the same selection system is hard to say.
You have to ask what values shape them and their motivations.
This brings me to the second lesson, which is in what Mr Dhanabalan said about how they were not motivated to make any changes to the system.
Singapore was fortunate that the country did not require them to do so, a testimony, perhaps, to Mr Lee's policies that made Singapore successful then. They didn't need changing and Mr Goh and his team built on them to drive the country forward.
But what if circumstances demand change and the old formulas no longer work?
Would the selection process be found wanting then, attracting people unable or unwilling to make the necessary changes because they share the same mindset and worldview of the incumbents?
It is a pertinent question to ask of the current 4G leadership, drawn mainly from the same small civil service pool but facing a radically different world facing disruptive change.
Will Singapore be as fortunate as in Mr Goh's time when change was not required?
And if it isn't, who or what will provide the impetus to transform?
Finally, the book is about leadership: Mr Goh's brand was not just different from Mr Lee's but he had to exercise it when the latter's influence still loomed large.
He was obviously a man of considerable ability. Otherwise, he would not have lasted under Mr Lee's watch and earned the respect of his equally talented colleagues.
But leaders need to have a vision for their team and the country.
When asked, Mr Goh said his was a very simple one: "Why was I in it for? And why was I picked? So, I come back to what I have said quite often: Keep Singapore going - I kept it simple on purpose. I did not want to raise expectation nor be weighed down by the enormity of the task. So, no highfalutin or pretentious slogan. At the back of my mind, I was deeply concerned that Singapore must survive, grow, prosper after Lee Kuan Yew had left the scene, and that the responsibility has fallen on me and my colleagues."
It is not difficult to understand his thinking because the pressing question at the time was whether Singapore could survive LKY.
Making sure it would was worth devoting a lifetime to.
Mr Goh and his colleagues delivered on the promise.
But is that vision enough for today's generation, which has enjoyed peace and plenty all their life and for which survival is no longer an issue?
If it isn't, what possibilities can future leaders offer that can inspire and excite the people?
It's a question the 4G leaders need to answer.
• The writer is also a senior fellow at the S. Rajaratnam School of International Studies, Nanyang Technological University.
• Tall Order: The Goh Chok Tong Story is now available in bookshops.
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