Through a case study of a school parcel tax campaign in Pasadena in early 2010, this commentary examines several persistent dilemmas regarding the current condition of public education in California. Until the 1970s, public schools were mostly funded by local property taxes. Local voters could use their influence over local school boards to determine local property tax rates. Although this reflected the strong U.S. tradition of “local control,” it also led to significant inequities, due to the wide variations in wealth between affluent and poor communities. Since the late 1970s, funding for public schools in California has been primarily a state matter, but public schools are still governed by local school boards. State funding has sought to narrow the gap in per-student spending between wealthy and poor school districts, but at the same time, per-student funding has declined so dramatically that California now ranks 46th in per-student spending. Faced with these realities, advocates for public schools have utilized a measure unique to California—the local parcel tax—to supplement local school funding. This article looks at the strengths and weaknesses of the parcel tax as a source of school funding. It compares the Pasadena Unified School District with other districts that have waged parcel tax campaigns, and, through a case study of the Pasadena campaign, examines how the overall political and economic climate, the state law requiring a two-thirds margin to pass, as well as efforts by supporters and opponents of the parcel tax, shaped the outcome.