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In the United States there is, simultaneously, an abundance of unemployed lawyers and a significant unmet need for legal care among middle-class households. This unfortunate paradox is protected by ideological, cultural, and practical paradigms both inside the legal community and out. These paradigms include the legal chase for prestige, the consumer’s inability to recognize a legal need, and the growing mountain of debt new lawyers enter the profession with. This article will discuss a very successful National Lawyers Guild experiment from 1930s-era Philadelphia that addressed a similar situation, in a time with similar paradigms, by emphasizing community-connected lawyering. That is, lawyering where the attorney prioritizes the client, works and is active in the community he or she seeks to serve, practices preventive lawyering, and charges fees that a working-class or middle-class person can afford. This article then pulls this Philadelphia Experiment forward to our current time and discusses it in the light of other, more recent developments, including rural lawyer programs, the medical residency model, and crowd funding platforms. In doing so, this article hopes to equip today’s practitioners with ideas they could utilize to help bridge this gap between unmet legal needs and an oversupply of lawyers.