This paper, originally published in the NYU Journal of Legislation and Public Policy, discusses a wide array of issues arising from the use of Section 501(c)(4) social welfare organizations to conduct the lobbying necessary to advance charitable goals. The paper goes on to propose an innovative legislative change that would allow the creation of a “separate segregated lobbying fund,” to make it easier for charities to expand their lobbying capacity without having to build and manage a separate legal entity.