Politics in Singapore is often regarded as a product of merit rather than legacy.

However, Lee Hsien Yang’s recent moves suggest a different approach—one rooted in legacy, rebellion, and whispers of dynastic ambition.

Lee Hsien Yang, once a quiet fixture in Singapore's elite circles, has increasingly stepped into a role as an unlikely dissident, raising questions about his true intentions and psychological motives.

Many who have closely followed Lee Hsien Yang’s public life note an undercurrent of frustration – perhaps even a hint of regret – surrounding his exclusion from contention for the premiership.

Through the years, his demeanour has occasionally reflected a quiet but discernible tension, a seeming resentment directed at what some view as a missed opportunity.

“His actions suggest a sense of capability on par with his brother, and perhaps a lingering discontent over his exclusion,” observe seasoned media members familiar with his trajectory.

Such exclusion, if indeed deeply felt, might represent more than mere sibling rivalry; it may hint at an enduring struggle with unresolved ambitions that extend back decades.

Lee Hsien Yang was always in the shadows of his brother

After Cambridge (class of ’79), Lee joined the army, taking a year off to earn his MS in management science at Stanford in ’89. Lee spent 15 years in the military; his last post before he parachuted into Singtel in 1994 where he was appointed director of the joint operations and planning directorate, later becoming CEO.

In Lee Kuan Yew's memoir From Third World to First: The Singapore Story, the elder statesman celebrated Hsien Loong’s accomplishments but seemed guarded when discussing Hsien Yang.

Five of the nine pages dedicated to the Lee family delve into Hsien Loong’s stellar academic achievements, his swift ascension through Singapore’s military, political, and governmental ranks, and his steady guidance of the economy during challenging times.

“Loong was always interested in what was going on in the country and in government,” his father writes with pride. Anecdotes abound—stories of Hsien Loong learning Malay, raising an albino son, and battling cancer—offering a deeply personal glimpse into his life and character.

By contrast, Hsien Yang’s portrayal is sparse.

Described briefly as a Cambridge First, Hsien Yang is noted to have had “the potential to be head of the civil service, [but] preferred the challenge of the private sector.”

When critics accused his appointment as Singtel’s CEO of being nepotistic, Lee Kuan Yew defended it as a decision rooted in meritocracy: “It would have been a disaster for him, and for the system of meritocracy that I had set up, if he had been appointed because of me. The officers he served with and his peers knew better,” he asserted.

“So did the fund managers. Singtel shares did not weaken.”

Lee Kuan Yew overhyped Hsien Yang's credibility - or at least tried to

Many Singaporeans, however, may find that last statement by Lee Kuan Yew hard to reconcile with Hsien Yang’s track record at Singtel.

By the time he had taken his $17 billion bid for Optus in 2001, investor confidence had already faltered, with shares dropping 22 percent that April. Despite the global telecommunications sector’s surge, Singtel’s performance under his six-year tenure remained largely stagnant—a source of contention among Singapore’s fund managers and a stark contrast to his brother’s celebrated rise.

Singtel under Lee was ranked the 18th greatest wealth destroyer in a 2001 study of 5,069 global firms by The Economist.

Hsien Yang’s resignation from Singtel in 2007 fuelled online speculation, with rumours of marital issues related to alleged infidelity with a Singtel-Optus employee in Perth. However, this remains unproven.

On Lee's resignation, Lee told a press conference that year he did not have a specific reason for wanting to step down. “It’s really hard to find a reason. At some point in time you decide that you have been in a role for some time and you would want to look for change, and 12 years us a very long time for tenure of any CEO."

There was dark talk of new jobs for Lee Hsien Yang.

A mid-ranking ambassadorship was mooted and then dismissed because, as one telecommunications analyst who knows him put it, "he doesn't like travelling, he really is a hometown boy". Speculation had it that he might move over to the Singapore Press Holdings board or go back to the military. Or, like his higher-achieving elder brother and dynamic father, perhaps move into politics.

But politics was out. “I’ve said many times before that I do not think politics is something I am suited for. I have no great interest to pursue a career in politics,” Hsien Yang said at the time.

Another former Singtel executive found the statement shoddy given that both Hsien Yang and Suet Fern had long thought that Hsien Yang was destined to helm the position for the nation's coveted office, even suggesting that this legacy was one their son might eventually continue.

“You could sense a shared conviction between them that perhaps the PM’s office was their family’s by right."

Despite claiming that he is not interested in politics, Hsien Yang joined Progress Singapore Party in 2020. Netizens were quick to accuse Hsien Yang of joining politics to spite his brother as part of their long-running feud over the fate of their father's house in Oxley Road.

In 2024 exclusive interview with The Financial Times, Lee Hsien Yang and Suet Fern expressed concerns that Hsien Loong used state mechanisms to hinder their branch of the family from entering politics, particularly regarding any future political aspirations of their son, Li Shengwu.

Ego, power, and legacy

Whether Lee Hsien Yang’s journey is driven by resentment or dynastic illusion, his ambitions appear to be shared by his family. His son Li Shengwu is said to represent the embodiment of their collective aspirations, a future once envisioned for Lee Hsien Yang himself.

While Lee’s public image remains that of a disciplined businessman, those close to the family note an intricate web of frustration, ambition, and a lingering belief in a legacy they feel was unjustly denied.

Lee Hsien Yang’s evolving role has raised many questions. His story is almost Shakespearean, with denied ambitions morphing into a personal rebellion, a legacy quest that he may now hope his son will fulfil.

Perhaps what is most perplexing to Singaporeans is this lingering notion of leadership as family inheritance.

Such dynastic perceptions seem out of sync, even dangerously detached from reality in a society like Singapore that is deeply rooted in meritocratic ideals, albeit with a smattering of cronyism.

As Lee Hsien Yang’s saga unfolds, his motivations remain shrouded in mystery, hinting at a personal journey not yet complete—a rebellion against legacy, or perhaps a rebellion for it.