Winston Cheng – GC Powerlist
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Southeast Asia 2025

Transport and infrastructure

Winston Cheng

General counsel | Land Transport Authority of Singapore

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Southeast Asia 2025

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Winston Cheng

General counsel | Land Transport Authority of Singapore

Team Size: 60

The team is providing legal support for the deployment of autonomous shuttles for intra-town trips. This involves making use of an existing legislative framework to trial the use of autonomous vehicles, as well as modifying the application of other legislative provisions in the context of using the vehicles as public service vehicles for scheduled, fare-paying services.

The team is involved in the crafting and modification of existing arrangements and contractual mechanisms to facilitate the transition of public transport bus fleet to Electric Vehicle (EV) Buses and the integration of EV charges into the existing public bus ecosystem.

In the lead up to the unveiling of the first train for the Singapore-Johor Bahru Rapid Transit System Link (RTS Link) in June 2025, the team rendered legal assistance in the preparation of agreements between LTA and various stakeholders involved in the project. In addition, the team is also involved in advising on regulatory-related matters under the relevant cross-border legislation.

Just last year, the team was closely involved in the provision of drafting and advisory support for the documentation relating to the Jurong Region Line (JRL) operator tender award. The JRL will be Singapore’s seventh MRT line, serving both existing and future developments in the western part of Singapore. It will significantly improve connectivity of the region and support the development of the Jurong area.

How do you approach managing legal aspects during periods of instability or crisis to ensure the organisation’s resilience?

My approach to managing legal aspects during periods of instability is focused on three areas, (a) comprehensive governance framework within the Legal team; (b) proactive risk management; and (c) operational resilience.

We have a comprehensive governance framework, with clear processes and decision matrices that guide our responses during periods of instability. This includes proper escalation pathways and systemic reporting structures to management. The Legal team is equipped to respond swiftly in the event of any instability or crisis. Proactive risk management is also key. Through preventive risk oversight, the team constantly assesses legal exposures, monitors regulatory changes, and develops targeted risk mitigation plans. This forward-looking approach helps us anticipate challenges and risk-manage before issues escalate. We also have operational resilience. We have focused on strengthening our legal capabilities through cross-training between the different divisions within Legal, developing standardised templates and a common pool of resources and maintaining strategic partnerships with panel law firms to ensure access to specialised expertise.

General counsel often speak of the need to be strategic to reach the pinnacle of the profession. How are you strategic?

In my view, being at the pinnacle of a profession does not have to mean that you are at the top of a hierarchy. What is important is that we must always do what is right and uphold the rule of law, no matter how difficult it is.

What do you think are the most important attributes for a modern in-house counsel to possess?

We should possess strategic vision, have strong legal fundamentals, and be adaptable in this fast-changing world.

Based on your experiences in the past year, are there any trends in the legal or business world that you are keeping an eye on that you think other in-house lawyers should be mindful of?

AI and automation have dominated the world, including the legal profession. As in-house lawyers, we need to keep up with such developments.

Winston Cheng - Southeast Asia 2022

General counsel | Land Transport Authority of Singapore

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Winston Cheng - Southeast Asia 2024

General counsel | Land Transport Authority of Singapore

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