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The most stringent anti-sprawl measure adopted by any American state is Oregon's urban growth boundary (UGB) program. Urban growth boundaries are lines on maps within which high-density development is encouraged, and beyond which such development is generally forbidden. Outside the boundary, rural industries (such as logging) and open space are promoted. This Article focuses on three issues: whether UGBs are constitutional under recent Supreme Court case law, (2) whether the UGB has in fact saved Portland (Oregon's largest city) from the social problems caused by sprawl, and (3) whether the side effects of UGBs make them a cure worse than the disease of sprawl. The article addresses issues (2) and (3) by comparing Portland to three metro areas of comparable size and regional growth rates: Seattle, Denver, and Salt Lake City. The article concludes that: (1) Oregon's UGB presents no constitutional problem, (2) the UGB has promoted infill development within the city of Portland, causing the city to be more prosperous than comparable cities, and (3) that housing prices have not increased more rapidly in Portland than in comparable cities, a fact which suggests that the UGB's effect on housing prices has been minimal. In other ways, Portland has continued to evolve in the same directions as nearby metropolitan areas without UGBs. On the negative side, this means that the UGB has not had an enormous effect upon automobile use, traffic congestion, or urban consumption of farmland. Although Portland's air is cleaner than it was a decade ago, the same is true for other western cities without UGBs. On the positive side, the UGB has not led to the horrors imagined by UGB critics. Portland's real estate is not significantly more expensive than that of comparable western cities, its traffic congestion is no more annoying, and its air is no more polluted. In sum, UGB supporters and opponents alike may have overestimated both the positive and negative effects of UGBs.