The Big Dig The Big Dig

Highway Teardown Tour | 11. Boston, MA

Jul 22, 2026 · 40m

Summary

Host Ian Koss explores the final chapter of Boston’s Big Dig: the creation of the Rose Kennedy Greenway. Guests Chris Cook and Stephanie Pollack discuss the park’s fraught history, from legal battles over green space to funding crises and the debate between open space versus cultural buildings. They also examine lessons for other cities rethinking downtown highways, emphasizing that infrastructure projects must serve as better neighbors rather than just being torn down.

Topics discussed

Introduction and the podcast's unexpected journey The Highway Teardown Tour and the Greenway's origins Guest introductions: Chris Cook and Stephanie Pollack Early activism and the Conservation Law Foundation's role Ownership disputes and the 'urban void' era Resolving the funding crisis and lease agreements Engineering challenges and alternative design visions Debate: Open space vs. built structures The value of passive parks and community programming Sponsors and break Federal Highway Administration and national teardown efforts Case study: Improving infrastructure in Birmingham, AL Favorite Greenway spots and final thoughts on teardowns Outro and credits
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