A look at Lee Hsien Loong's 20 years as Prime Minister
At age 52, Lee Hsien Loong became prime minister and led Singapore for 20 years.
He anchored the country through multiple periods of uncertainty – from global economic challenges to the Covid-19 pandemic.
In his personal life, he has also overcome adversity — he has beaten cancer twice, and went through a very public and ugly dispute with his siblings.
2004 Became Singapore’s third prime minister
Lee Hsien Loong was sworn in on Aug 12.
In his first National Day Rally less than two weeks later, Lee said: “I can't promise air-con coaches to take us to the destination in comfort. But we can provide everyone with good coaching, running shoes, water to drink, and first-aid stations along the way.”
Not afraid to embrace new ideas, he proposed a five-day work week for civil servants and the controversial idea of having casinos in Singapore.
2005 Integrated Resorts to ‘reinvent Singapore’
Concerned by the potential harm to society, the Government had long resisted setting up casinos.
But in April, Lee told Parliament the Government will be developing two Integrated Resorts at Marina Bayfront and Sentosa. The IRs – with hotels, malls and convention spaces – will give Singapore the “X-factor” and “buzz”, he said.
2006 First General Election as PM
In a landslide victory, Lee led the People’s Action Party to win 82 out of 84 seats in the GE.
Lee unwittingly introduced the term “mee siam mai hum” (he meant to say “laksa mai hum”) into Singapore lingo during his National Day Rally speech, when he was showing how he could connect with heartlanders as easily as local blogger Mr Brown’s bak chor mee man.
2007 ‘Keeping the status quo’ on Section 377A
One of the most contentious issues during Lee’s time in office was Section 377A of the Penal Code, which criminalises sex between men but not enforce it. An open letter was sent to Lee in October and an online petition garnered 2,341 signatories to appeal for Section 377A’s repeal.
After a two-day debate in Parliament, the Government struck a compromise to retain the law. Lee said: “If we force the issue and settle the matter definitively one way or the other, we will never reach an agreement. Instead of forging a consensus, we will divide and polarise our society.”
Some 15 years later, in November 2022, Parliament voted and repealed the decades-old law.
2008 Singapore wins right to host first Youth Olympic Games
In 2007, Singapore submitted its bid to host the inaugural Youth Olympic Games – aimed at inspiring youths to spend more time on sports, and less on the Internet and television. In February 2008, Lee and hundreds of Singaporeans erupted with joy at the Padang when it was announced that Singapore would host the games in 2010.
2009 First drawdown of past reserves
Singapore slid into recession following the collapse of American investment bank Lehman Brothers in September 2008.
In January 2009, while the Cabinet considered the proposed Budget, Lee informally discussed with then-President SR Nathan on the need to use past reserves to support the Budget measures.
Mr Nathan would later approve the first-ever drawdown on Singapore's past reserves – $4.9 billion to fund two special schemes.
2010 His mother’s death
On Oct 2, Lee’s mother, Kwa Geok Choo, died at age 89. In a eulogy, Lee said his mother had “quietly contributed to Singapore”. “All of our lives, Mama has been there for us. We have rejoiced together, grieved together, and shared critical moments together,” he added.
2011 Lunchtime apology during GE rally
Amid public unhappiness over higher housing prices and overcrowding on public transport, Lee made a rare apology for mistakes his government may have made.
At a GE lunchtime rally in Boat Quay, he said: "If we didn't quite get it right, I am sorry, but we will try and do better the next time.”
The PAP later clinched 81 of the 87 seats, with the five-seat Aljunied GRC won by the Workers’ Party. It was the first time the ruling party had lost a GRC, which also saw the loss of two full ministers and a senior minister of state.
2012 Social media debut
With photos of his #jalanjalan selfies and throwback shots, Lee is one of the most followed public figures in Singapore on social media — with 1.7 million followers on Facebook and more than 730,000 on Instagram.
In April, Lee put up his first post — a “welcome” note — on Facebook. “Many of my colleagues have been using social media, including Facebook. Having watched them, I have decided to join the fun,” he wrote.
2013 First National Day Rally at ITE College Central
Lee delivered his ninth National Day Rally speech at ITE College Central in Ang Mo Kio for the first time. The rally was previously held at the University Cultural Centre in the National University of Singapore.
“I brought the Rally to ITE to underscore my longstanding commitment to investing in every person, every Singaporean, to his full potential,” he said.
Noting that Singapore is at a “turning point”, he then announced a swathe of changes to expand social safety nets and make society more equitable, such as MediShield Life and HDB grants for middle-income Singaporeans.
2014 Sings xinyao tune at the National Day Rally
In his Mandarin speech, Lee took a lighter approach to drive home a point that there are many opportunities for Singaporeans to fulfil their dreams — by singing a line from Small Stream That Flows Forever, a tune by xinyao pioneer Liang Wern Fook.
2015 Prostate cancer and Lee Kuan Yew’s death
Lee had already survived a bout of cancer after being diagnosed with lymphoma in 1992. In January 2015, he revealed he had prostate cancer. He later went through surgery and took a week of medical leave.
The nation grieved with Lee after his father, founding prime minister Lee Kuan Yew, died on March 23. In his eulogy, he said: “He went away peacefully... But his values, his love, and his words – these will stay with us, inspire us, and live on in us for a long, long time.”
2016 Feeling faint at the National Day Rally
The audience gasped when Lee slouched over the lectern midway through his speech. Lee, who was helped off the stage, was reportedly feeling unsteady because of prolonged standing, heat and dehydration.
He resumed his speech an hour later.
2017 Oxley Road dispute with siblings
In one of the rockier periods in the life of the Lee family, Lee’s younger siblings — Lee Wei Ling and Lee Hsien Yang — accused him of misusing his power when handling the matter of their late father's house at 38 Oxley Road. On June 19, Lee apologised for the publicly aired dispute, saying it had damaged Singapore's reputation and affected confidence in the Government.
2018 Hosting Donald Trump and Kim Jong Un
The words ‘shocking’ and ‘incredible’ were used by political observers when Donald Trump and Kim Jong Un exchanged handshakes at Capella Hotel in Sentosa on June 12. It was the first-ever meeting between leaders of North Korea and the United States. Lee and Kim also discussed bilateral relations, and developments in North Korea and the region. Trump was presented with a birthday cake during a working lunch with Lee and other officials at the sidelines of the historic summit.
2019 Appoints Heng Swee Keat as Deputy Prime Minister
In a move that signalled progress in Singapore’s leadership transition, Lee appointed Heng Swee Keat, 58, as DPM in April. Lee, who was 67 then, had previously said he hoped to step down before his 70th birthday. Heng took himself out of the running as Singapore’s leader two years later, saying he was stepping aside for someone younger with a “longer runway”.
2020 Pink shirts and magic cup
Lee’s wardrobe choice was given coverage as pink shirts became a staple of his television appearances. He said it was because his TV producer told him to.
Another meme-worthy image that tickled netizens during the Covid-19 pandemic was a blue ceramic cup that usually appeared every time Lee made a national address with a Covid-19 update. And he seemingly was able to speak in a different language each time he took a sip from the ‘magic’ cup.
2021 Covid-19 booster
On Sept 17, a chirpy Lee rolled up his sleeves and took a Covid-19 booster shot at the Singapore General Hospital. “If you are offered a booster, please take it. It will reduce your chances of getting seriously ill, or needing ICU care,” he wrote on Facebook.
2022 Made Lawrence Wong Deputy Prime Minister
Lee made it even clearer who was in line to succeed him when he promoted Lawrence Wong to DPM in June. This came after Wong was picked as the PAP’s 4G leader two months earlier.
2023 Political succession 'back on track'
Lee shelved his plans to step down before he turned 70 because of the Covid-19 pandemic. In his National Day Rally speech, he said: “Now Covid is behind us, and my succession plans are back on track.”
2024 PM Lee steps down
Lee announced that he will step down on May 15. In his final major speech as PM, Lee said at the May Day Rally: "I have done my duty, and I am very happy that I chose this path of public service all those years ago."
On May 15, 2024, Lee formally handed over the reins to Lawrence Wong. At the inauguration ceremony, Lee was also sworn in as Senior Minister and will remain in PM Wong's Cabinet. 

PRODUCED BY: Ching Shi Jie, Low Ching Ling, Desmond Chua, CJ Foo, Michal

PHOTO CREDITS: The Straits Times, MCI, Facebook/Lee Hsien Loong