There is no question that Lee Kuan Yew's vision, skill and tenacity built Singapore from a tiny imperial backwater in Southeast Asia into a shimmering centre of international finance, where income levels are far higher than in Canada.

Few statesmen are as singularly identified and intertwined with their country's progress and global stature as Mr. Lee is with Singapore. And his death at the age of 91 has prompted an outpouring of appreciation from both Singaporeans who owe him their prosperity and world leaders who recognize his leadership. He was Singapore's prime minister for three decades, and wielded enormous influence as a cabinet-level adviser even after he stepped down. Richard Nixon – though hardly an arbiter of moral leadership – once mused that in another time and another place Mr. Lee might have "attained the world stature of a Churchill, a Disraeli, or a Gladstone." To many in a rising Asia, Mr. Lee doesn't need fading, anglophile references such as these.

But his passing also prompts a number of questions about what the world can learn, and should remember, about his life and legacy as one of Asia's most memorable postcolonial leaders. A ruthless authoritarian who delighted in persecuting his opponents – "Everybody knows that in my bag I have a hatchet, and a very sharp one," he said – Mr. Lee was also an unabashed champion of the "Asian values" argument that civil and political rights, such as freedom of speech and assembly, needed to be subordinate to the economic and social rights of material well-being and security. These two defining characteristics of Mr. Lee's leadership seem at odds with the Asia of today, to say nothing of the many lives he ruined in order to maintain power and his stunting of Singapore's politics – where his eldest son, Lee Hsien Loong, is prime minister today.

Story continues below advertisement

As the world remembers Mr. Lee and his successes (as well as his quirky opposition to chewing gum and jukeboxes), it is worth recalling those who dared to oppose him over the years. Many were battered into bankruptcy or prison by Singapore's harsh criminal defamation laws. Under Singapore's constitution, they were then prohibited from running for public office.

Chia Thye Poh, a physics lecturer and member of parliament in 1966, is one of them. He was detained for 23 years without charge and then confined to house arrest on Singapore's Sentosa island for nine years. Mr. Lee refused to pardon him, and restrictions on him were only lifted in 1998.

Chee Soon Juan is another. A lecturer and secretary-general of the opposition Singapore Democratic Party, Mr. Chee was fired and sued after an election in 1993. In 2001, Mr. Lee sued him personally, bankrupting him. Mr. Chee has been jailed more than 10 times. "I've lost count," Mr. Chee has said.

Joshua Benjamin Jeyaretnam, a former leader of Singapore's Workers' Party and a senior judge, is yet another. In 1981, he became Singapore's first opposition MP, but after being sued multiple times, including by Mr. Lee, he had bankruptcy proceedings brought against him and was eventually forced from office.

Mr. Lee, no fan of corruption, was also no fan of the press, strictly limiting domestic criticism, occasionally banning foreign publications and launching countless defamation suits. After British journalist Alan Shadrake wrote a critical book about Singapore's justice system and its use of the death penalty, he was arrested – and at the age of 76, was locked away for two months in 2011. "I am not at all impressed by the carefully nurtured Lee myth. This was the man who got rid of all opposition leaders or critics and ensured the media he didn't destroy remained strictly under his control," Mr. Shadrake wrote to me in an e-mail.

There are countless others. But Mr. Lee justified his actions, and crackdowns such as one in 1987 against a "Marxist conspiracy," as necessary to maintain stability.

His death, this week, was mourned by many – including likely suspects who take similar political approaches. India's hardline Prime Minister Narendra Modi tweeted that Mr. Lee's "life teaches valuable lessons for everyone." Babatunde Fashola, the successful but soft authoritarian governor of Lagos who has demolished slum dwellings, tweeted: "He was an inspiration."

Story continues below advertisement

The renown Mr. Lee garnered for his successful city-state, of course, took place in a broader context in which South Korea and Taiwan were also seeing economic gains under authoritarian rule. But both Taiwan and South Korea have transitioned, arduously, to democracy. Even Indonesia, after three decades of a much less benevolent dictator in Suharto, elected an outsider. Mr. Lee's views may still prompt grins in Beijing and provide grist for philosophy classes, but as a unifying vision for Asian political systems, it seems increasingly dated.

Singapore will never forget Mr. Lee as its founding father – as it has never really forgotten Sir Stamford Raffles, who chose Singapore's location as a trading port in 1819 – but it will now have to move on. Mr. Lee's party, like the Barisan Nasional in Malaysia, is at once the natural governing party and increasingly unpopular.

"His death [is a] watershed moment in Singapore's history," University of British Columbia assistant professor Kai Ostwald wrote to me. "Without question, it will mark a clear transition into a new era for the country, at least symbolically."

Mr. Chee, who is still living with the effects of Mr. Lee's persecution, offers a hopeful perspective on Singapore's new era.

"I prefer not to dwell on the personal side of things even though I've been jailed, made bankrupt and barred from elections," Mr. Chee wrote in an email. "Lee Kuan Yew has passed away and I've sent my condolences to the family. What I am concerned about is the future of Singapore. For the country to progress, we need to democratise and the people need to be free."