Two Decades of Leadership: PM Lee’s Key Moments and Decisions

From family disputes to pandemic management, a look at how Lee Hsien Loong navigated challenges as Singapore’s Prime Minister.

For 20 years, Prime Minister Lee Hsien Loong has led Singapore through pivotal moments that shaped its economic, political, and social landscape. Known for his meticulous and pragmatic approach, Mr. Lee often seeks diverse viewpoints before making decisions. Cabinet colleagues recall his ability to separate personal matters from public duties and his willingness to tackle difficult decisions for the country’s benefit.

The Oxley Road Saga
In 2017, a public dispute between Mr. Lee and his siblings over the fate of their family home, 38 Oxley Road, brought private matters into national focus. Accusations of misuse of power and conflict of interest emerged, prompting Mr. Lee to address Parliament with a ministerial statement. Despite the deeply personal nature of the disagreement, Mr. Lee recused himself from government decisions related to the house, ensuring transparency. A ministerial committee explored options for the historic property, eventually presenting multiple proposals.

Senior Minister Teo Chee Hean, who chaired the committee, noted Mr. Lee’s ability to remain objective, despite the personal toll. “PM was very clear he was not going to be involved in the decision,” he remarked, emphasizing the Prime Minister’s commitment to public accountability.

Integrated Resorts and Casinos
One of Mr. Lee’s earliest major decisions was the introduction of integrated resorts (IRs) with casinos. Despite divided opinions within the Cabinet, Mr. Lee facilitated open discussions, ensuring all views were considered. The economic benefits were weighed against potential social issues, leading to the establishment of safeguards such as entry levies for locals. The move marked a turning point in Singapore’s tourism and economic strategy.

The 2011 General Election Loss
The loss of Aljunied GRC to the opposition Workers’ Party in the 2011 General Election was a significant moment in Mr. Lee’s tenure. The election reflected public discontent over issues such as housing and transport, influenced by policies implemented during the global financial crisis. Mr. Lee initiated a post-election review to identify areas for improvement, ultimately strengthening the People’s Action Party’s strategy in the era of social media.

Fixing the MRT System
In 2015, Singapore faced one of its worst MRT disruptions, prompting Mr. Lee to dive into the technical details personally. Collaborating with then-Transport Minister Khaw Boon Wan, Mr. Lee analyzed engineering data and introduced measures to rebuild public confidence. His hands-on involvement underscored his problem-solving approach and dedication to addressing pressing national issues.

The COVID-19 Pandemic
The pandemic tested Mr. Lee’s leadership in unprecedented ways, delaying his planned succession. Balancing public health with economic sustainability, Mr. Lee relied on input from experts and ministers while ensuring Singapore remained a global aviation hub. His steady guidance through the crisis reaffirmed his commitment to seeing the nation through challenging times before transitioning leadership.

A Legacy of Growth and Resilience
Reflecting on Mr. Lee’s tenure, colleagues highlight his discipline, patience, and unwavering focus. Senior Minister Teo observed a shift in Mr. Lee’s leadership style, with a growing emphasis on understanding and managing people. Former Cabinet member Lim Swee Say praised Mr. Lee’s positive energy and ability to inspire his team.

As Mr. Lee prepares to hand over the reins to Lawrence Wong, his two decades of leadership leave a legacy of resilience and adaptability in the face of complex challenges.

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