EP.31 / Randall Winston


Rebuilding in LA's Pacific Palisades neighborhood (Source: AP News)

LA's Capital Infrastructure Program, Rebuilding the Palisades, and Preparing for the 2028 Olympics

Randall Winston is the Deputy Mayor of Infrastructure for the City of Los Angeles. His portfolio covers everything in the public right of way, including street services, engineering, street lighting, sanitation, and transportation. Randall is currently doing something no one in his role has done before: building the city's first comprehensive, multi-year capital improvement plan.

Randall and I go back almost 20 years to UVA, where he wrote his graduate thesis on LA infrastructure as a master's student. His path since then has included law school, the U.S. Army National Guard (where he still serves as a Lieutenant in the Reserves), and eventually City Hall. In this episode, he makes the case that a disciplined, data-driven capital plan is the foundation LA needs to finally deliver on the potential the city has always had.

Of course, we can't talk about LA's infrastructure without addressing the 2025 wildfires and what it will take to make the city more resilient. Randall walks us through the city's five-year plan to underground 45 miles of utilities in the Palisades, and why he's cautiously optimistic about federal funding for that work despite the political headwinds.

Plus, we talk about 2028: what pedestrian and bike connections are being built to serve Olympic venues, the fan zone strategy being tested through FIFA this summer, and how the Games are accelerating improvements the city will benefit from long after the closing ceremony.


About Randall Winston

Randall Winston’s career spans law, architecture, and public service, which collectively have shaped a career focused on advancing equitable, sustainable development. Randall serves as Deputy Mayor of Infrastructure for the City of Los Angeles, where he leads Mayor Karen Bass’ infrastructure policy and alignment of public works and transportation investments. Previously, he was an attorney at O’Melveny & Myers where he represented government and environmental organizations facing complex litigation and state and federal investigations.

Prior to his legal practice, Randall was appointed by Governor Jerry Brown to serve as Executive Director of the California Strategic Growth Council, a state agency integrating efforts to achieve the state’s climate and sustainable community goals. Under his leadership, SGC invested over $1.3 billion in transit-oriented affordable housing, land conservation, and capacity building in the most under-resourced communities throughout California.

Randall also served as an advisor to Governor Jerry Brown, where he worked across state agencies to lead implementation of Executive Orders on green buildings and electric vehicles, including development of unprecedented regulations to reduce emissions from the building and transportation sectors. He also led the planning and execution of trade missions to China and Mexico, working with foreign government officials and businesses across the state to forge international trade and environmental agreements.

Before serving in the Brown administration, Randall worked for Pritzker Prize-winning architect Norman Foster, collaborating with interdisciplinary teams on design, urban planning, and infrastructure projects throughout the world. He also spent two years working for urban development and architecture firms in Beijing, China.


Topics Covered

  • How architecture, law school, and the military shaped Randall's approach to public service

  • Day-to-day responsibilities of the Deputy Mayor of Infrastructure

  • Why LA is the only major U.S. city without a capital improvement plan

  • How the new CIP will change the way projects get prioritized and funded

  • Why resurfacing a street legally triggers a much larger project

  • Inside the infrastructure response to the January 2025 fires

  • What's being built to get LA ready for 2028

  • Randall's vision for LA in 2035

  • Three must-visit places in LA

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EP.30 / Alan Pullman