Portland boosters invited Lewis Mumford and Robert Moses to Portland to comment on the growth of the city and the region in the years surrounding World War II. Mumford emphasized regionalism and a dispersal of the population to new towns, which would be satellites to the central city, strengthened as a regional centre. Moses, coming to Portland just five years later than Mumford, stressed freeway, bridge and park development, with a mind toward girding the city for post-war growth. In the mid-century, Portlanders were more inclined to adopt Moses' suggestions, almost all of which were eventually implemented. A shift in political culture in the 1960s and 1970s, however, brought a renewed commitment to the ideals Mumford had espoused and, today, the Portland area's regional planning agency, Metro, has adopted a Regional Framework Plan that embraces the Mumfordian vision, with an almost blatant rejection of Moses' commitment to freeways, bridges and other types of massive investment in auto-accommodating infrastructure. This paper discusses the difference between the two paradigms of planning and provides some explanations for the shift in the Portland region from a Mosesian to a Mumfordian ideal.