SINGAPORE &ndash It was the year 2000 and the start of a new millennium. At the time, property tycoon Kwek Leng Beng&rsquo s elder son, Sherman, was all of 25.

 

The proud father in an interview detailed how his son was gaining exposure in Silicon Valley, at the cutting edge of entrepreneurial developments, and trying to strike out on his own.

 

The older Mr Kwek was 59 then, already fielding questions on who would succeed him in heading his business empire.

 

But fast-forward 25 years, and the father and son are now embroiled in a public battle over property giant CDL, with the father, who will be 84 in 2025, trying to fire the son, now 49, from being group chief executive of the company.

 

What happened in the intervening 25 years to turn father and son against each other is a complex web that is still being untangled, littered with what the older Mr Kwek calls missteps and a corporate governance issue that crossed &ldquo a red line&rdquo .

 

In 2000, the young Mr Sherman Kwek was already in the public eye, thanks to his famous father, who made the list of one of the world&rsquo s 50 richest Chinese people in 1995.

 

But he did not want to join the family business back then, which encompassed the sprawling Hong Leong Group that controlled Singapore&rsquo s two largest and most profitable property development companies &ndash City Developments and CDL Hotels.

 

Instead, he wanted to set up his own dot.com business after graduating from Boston University.

 

In his interviews at that time, Mr Kwek was sanguine about his son not joining his business, which was also handed down to him by his father, Mr Kwek Hong Png, who died in 1994.

 

At a results briefing in 2011, Mr Kwek said: &ldquo I am not averse personally to getting an outsider to come and run the company... if my relatives or my son cannot perform.&rdquo

 

His remarks then were made even as Mr Sherman Kwek had finally joined the family business in 2010, serving as chief executive of CDL China. Mr Kwek also has a younger son, Kingston, who is a stock trader in his early 40s.

 

And in 2014, the company appointed a new chief executive who was not a Kwek for the very first time &ndash an Australian, Mr Grant Kelley, who was previously with a private equity fund.

 

But three years later, Mr Kelley resigned, and Mr Sherman Kwek became the designated successor the following day, taking over the group CEO role in 2018.

 

Over the next few years, to people on the outside, things seemed to be going swimmingly, with father and son showing solidarity whenever the company faced any difficulties.

 

But on Feb 26, the listed company called for a trading halt and cancelled its results briefing. And it emerged that Mr Sherman Kwek had reportedly become entangled in a tussle for control over CDL with his own father.

 

The older Mr Kwek accused his son of bypassing the nomination committee to change the composition of CDL&rsquo s board. He called it an &ldquo attempted coup&rdquo and filed court papers to address it.

 

A closed-door High Court hearing on Feb 26 was held to hear Mr Kwek Leng Beng&rsquo s lawsuit against his son and several board directors.

 

In response, Mr Sherman Kwek said he was disappointed over the &ldquo extreme actions&rdquo taken by his father and said there was no intention to oust his father as chairman.

 

Earlier in February, Mr Kwek tried to get his son dismissed as group CEO, saying Mr Sherman Kwek was &ldquo consolidating power through the irregular appointment of two new directors&rdquo .

 

But the reconstituted board objected to the attempt by the chairman to fire the CEO.

 

Besides the corporate governance issues, the older Mr Kwek recalled the other times his son had put the company in &ldquo a precarious position&rdquo , spotlighting Mr Sherman Kwek&rsquo s debacle with Chinese developer Sincere Property Group that led to a loss of $1.9 billion for CDL in 2020.

 

During his tenure as chief executive of CDL China in the early 2010s, Mr Sherman Kwek said CDL had to play catch-up with other developers such as CapitaLand, which had entered the China market earlier.

 

In 2019, he was very optimistic about the Sincere investment, which was the group&rsquo s single largest investment in China. He said this would transform the company in China, where it was &ldquo very painful&rdquo to buy one project at a time over the last several years.

 

&ldquo Now we can seriously bulk up on scale and grow with our partner with the necessary expertise on the ground,&rdquo he said.

 

But these dreams of conquering the China market crashed and burned when Sincere started facing liquidity challenges.

 

Mr Sherman Kwek also faced some of his first public challenges to his leadership as three directors resigned in the space of three months in protest over the Sincere venture.

 

One of them is the cousin of the older Mr Kwek, marking one of the first public family rifts in CDL&rsquo s history. Mr Kwek Leng Peck resigned as a non-executive, non-independent director after holding the post for more than 30 years.

 

Ultimately, the deal that Mr Sherman Kwek once hailed as game-changing cost CDL almost all its investment.

 

But all that seemed to be water under the bridge for father and son, according to the biography Strictly Business released in 2023 about the older Mr Kwek.

 

He said at a results briefing in 2021 that &ldquo we should not keep talking about Sincere... We must now forget about all these old subjects&rdquo .

 

In the book, Mr Sherman Kwek called the episode &ldquo the darkest and most painful period&rdquo of his career, while saying he will &ldquo tread more carefully in the future&rdquo .

 

However, these old wounds seem to have resurfaced in the current battle between father and son. The older Mr Kwek said in his media statement: &ldquo I take my role as executive chairman seriously and have always prioritised the interests of all shareholders, not just those of my family.&rdquo

 

And apart from when Mr Kwek Leng Peck resigned over Mr Sherman Kwek&rsquo s business decisions, this is the first time the Kwek clan has been so publicly embroiled in a family crisis related to succession.

 

In 1994, when the pioneering Mr Kwek Hong Png died, media reports had suggested that there could be a struggle for control between his son, Mr Kwek Leng Beng, and his Kuala Lumpur-based nephew, Mr Quek Leng Chan.

 

However, the family rejected any talk of succession struggles and analysts back then felt that there was no problem with succession. Mr Kwek Leng Beng went on to inherit his father&rsquo s crown and by 1995, he was Singapore&rsquo s richest man, with an estimated fortune of US$5 billion.

 

The image of unity was upheld, with newspapers often running stories about the successful Kwek clan and its sprawling business empire held together in Singapore and Malaysia.

 

In 1997, a fellow developer even said he thought of the Kweks each time his children sang Old MacDonald Had A Farm.

 

&ldquo Why? Because midway in the song, the lyrics go: &lsquo And a quack, quack here, and a quack, quack there. Here a quack! There a quack! Everywhere a quack, quack!&rsquo ,&rdquo a report quoted him as saying, noting that Mr Kwek beamed at the joke and was said to have regarded it as a high compliment paid by a competitor to acknowledge his prowess at managing his empire.

 

When the question of his own succession arose in 2000, he had expressed reservations about the old way of doing things, where a family owns and runs the business.

 

These concerns were not unfounded when there were reports of public family divisions over family-run businesses. The Yeo family&rsquo s tussle over food and beverage company Yeo Hiap Seng, which pitted brothers and nephews against one another, in the early 1990s would have weighed on his mind.

 

In 2011, he even said he would rather get an outsider to helm the company if a successor could not be found within the family, calling it &ldquo silly&rdquo to let a family member run it if they were not able to do so.

 

Media reports at that time named candidates among the third-generation Kweks, which include Mr Sherman Kwek and Mr Kwek Eik Sheng, who is the elder son of Mr Kwek Leng Joo, Mr Kwek Leng Beng&rsquo s brother.

 

The anointing of Mr Sherman Kwek as CEO seemed to have settled the issue. But in the biography Strictly Business, it was noted that the decision on the next Hong Leong group leader still has to be made with the support of the other branches of the Kwek clan.

 

The very public spat between father and son has seen them pointing fingers at each other. In a statement on Feb 27, Mr Sherman Kwek said the underlying reason that led to the public fallout at the company was his father&rsquo s adviser, Dr Catherine Wu. Her official position is that of an adviser to the board of Millennium & Copthorne Hotels, a wholly owned and principal subsidiary of CDL Group.

 

The battle between the duo adds complexity to the issue of succession.

 

In the 2023 book, Mr Kwek said directly: &ldquo I nominate Sherman,&rdquo when addressing the question of who will inherit his crown.

 

But with the latest saga, the line of succession may no longer look so clear. Instead of the end of the story, it might just be the beginning of a brand new chapter.