Abstract: In 1976, the First National Bank of Boston, Gillette, and three other Massachusetts companies announced their plan to oppose a referendum authorizing a graduated income tax. State officials responded that Massachusetts law prohibited this type of corporate political expenditure. The U.S. Supreme Court intervened, declaring that Massachusetts could not prohibit speech based solely on the “corporate identity of the speaker.” The Court reasoned that shareholders through “corporate democracy” were better positioned than states to regulate companies’ political engagement. In the wake of this decision, the Boston City Council—a municipal corporation—announced its plan to spend its corporate dollars in support of a 1978 tax referendum. That same election, Massachusetts Citizens for Life—a nonprofit corporation—financed newsletters promoting anti-abortion candidates. State and federal officials again blocked these corporate political expenditures. This time, however, the Supreme Court protected only the nonprofit, observing that a “voluntary political association” did not “suddenly present the danger of corruption merely by assuming the corporate form.” These Supreme Court decisions armed business and nonprofit corporations with a powerful new weapon—the First Amendment—that future lawyers wielded against advertising bans, labor contracts, healthcare requirements, and, of course, campaign finance laws. At the same time, the decisions left the City of Boston unable to support referenda that the Bank of Boston was free to oppose. This paper will situate this “First Amendment libertarianism” in the political, legal, and social context of 1970s Boston, a city gripped by racial crisis and dependent on business corporations, especially the Bank of Boston, for financial survival. This context helps explain why courts, lawyers, and executives expected that shareholders could responsibly oversee governments better than governments could oversee shareholders—or themselves.